#842: “I have a much-older boyfriend who has seven kids. Is my situation ok?”


I’m 25 and currently semi-secretly dating a man 17 years my senior who has 7 children, one of whom is only 4 years younger than me. BF and I are coworkers, met at work a year ago and had an instant connection. A select few people at work know about us. They expressed surprise and confusion (and a little revulsion) at first, but seem to have accepted the idea.

His children and parents love me (his eldest child even gave me gift ideas for his birthday the first time I met her). The youngest five are from one mother and she takes care of them primarily, and BF has emphatically stated they are not my responsibility. A couple come over, I ask about school, let them play my Xbox, give them junk food and they go home. So that’s not really a problem.

Here are my main concerns:

1) Telling my family. I CAN’T. I love my parents so much but they are pure-hearted, frankly naive, upper middle class, white collar conservatives who want me to marry a dashing young astronaut. I can’t help but believe it would crush them and make me a pariah to my extended family, who are deeply religious and conservative (I’m the black sheep atheist though, so I’m kinda used to that). Script ideas?

2) His kids. SEVEN. From three different mothers! It took a while for me to put aside my prejudice and accept that he came from an abusive, broken family (13 siblings from 4 different mothers). He never had a proper family unit and views my own family with poorly concealed awe. Whenever he mentions my dad (who is thankfully old enough to be his father) there are stars in his eyes. STILL THOUGH. Guess I still can’t put it all aside…

3) MY kids. Still can’t decide if I want them, but I definitely want the option. He stated at the beginning he would never have more kids, but hinted recently he “might not be done yet.” Part of me really likes the idea, but another part is horrified at being the 4th mother of his children and asks me wtf I’m doing with my life.

4) The ageplay. As an example, if I tease him too much, he’ll tease back and say that I’m grounded unless I stop. Usually the convo has a sexual overtone. We’re just joking and honestly I really like it. But the fact that I like it makes me feel weird.

What’s happening? Is my situation okay or not? He’s a sweetheart. Gentle, loving, extremely witty, very protective. I’m very happy with him. Just getting a random hug from him makes me grin like an idiot, even after a year.

I feel conflicted and could use advice.

– In Over Her Head

Dear In Over Her Head,

You are the boss of you, and you are the only one who can decide if this relationship is adding happiness to your life. Neither I nor our kind commenters can decide what’s okay for you. If you decide to break up, nothing we said could keep you there, and if you choose to stay and be happy, no amount of doom and gloom from us can change that.

Let me put my own history & biases on the table: When I was 25 I had a short but intense (&unwise)(&hot) relationship with someone 30 years my senior (that I would have rather chewed off a body part than told my dad about) who had kids around my own age, and I heard a lot of romantic and sexy stuff from him about how magical and great my 25-year-old self was and how I was the One True Thing he’d been searching for all this time. I enjoyed myself a lot at the time in between bouts of agonizing about whether this was normal and wondering who could I tell about it.

At 42 I roll my eyes at the memory of basically every word that came out of both of our mouths. The “you’re grounded, young lady” jokes with accompanying sexual overtones are probably the least cringe-y thing I can remember because they were honest and funny. I could not have been talked out of anything back then, and you cannot be talked out of anything right now (nor should you necessarily be), but wow, my lens on all of that has changed with time. Now I know many times over the hard lesson that having great chemistry with someone is not always enough to build a happy life with.

What I’d like to do is to suggest some questions to ask before you think about getting very serious with your boyfriend, and especially before you think about having kids with him. Ask him, ask yourself, and ask the situation some questions. Off the top of my head:

Does he date or has he dated women his own age? For instance, are his prior serious partners roughly the same age as he is, or do they all trend younger? Does he have female friends his own age? How do women his own age in your office see him/interact with him/do they seem to respect him or do they roll their eyes at him? How does he treat & talk about women his own age? Age differences aren’t always a problem in romantic relationships, but there can be icky, sexist aspects to them. I would especially beware of someone who is in search of a “clean slate” or a “new beginning.”

Is he a good dad? Is he a great dad? Is he present in his kids’ lives, does he know all their ups and downs and stories about their days and their friends and stuff? Does he have the time & emotional bandwidth for all of them? Is he truly a partner with their moms in raising them (even if the romantic relationship soured)? Is he supportive financially? How do the mothers of his children talk about him?

If he is thinking about settling down and having kids with you, what does he think will go differently this time? I’m sure you’re pretty amazing, but I’m also pretty sure that the lady he had five kids with was also “amazing” once upon a time. People do learn and grow as they age, but the best predictor of future behavior is often past behavior. The kind of dad he is and has been is probably the kind of dad he will be. Is he good enough at it for you, to be the kind of dad you want for your theoretical future kids?

There’s maybe a story in here about someone who is very charismatic and good at beginnings but not so good at the middles of things. I would be very leery of anything that smacks of a redemption narrative, like, “Finally with you I will be the man I was supposed to be all this time.” :Cue 42-year-old-woman-eye-roll:

I think the secret nature of this relationship and how that all evolves in the next year or so will be a good test for you. Is it stable & happy & viable enough to make it worth running the Family Opinion gauntlet? Or does it only work for you if it stays a secret?

If you do decide to tell your folks about your boyfriend, the more basic the script the better, probably: “I’m dating ______. We met at work. I’m really happy so far.” The more matter-of-fact you can be about the facts that you know will worry them, like, “He’s been married before and has kids from prior relationships,” the more people *might* take their cue from you about how to react. When they raise objections to him, try a strategy of not arguing with them. “Yep, that gave me pause, too/I can see why that would raise some eyebrows/I had a lot of questions about that, too, etc…. but so far my fears have not been founded.” You don’t owe your parents living the exact life they pictured for you, but I think you’ll do better if you acknowledge why they might see some red flags (’cause you see some red flags, too).

Time and a track record of happiness & good interactions over time sometimes have a way of smoothing out family & friend (& advice bloggers) reactions to relationships that seemed shocking at first (just like at work, with your colleagues who had “revulsion” at first but have settled into acceptance). I’m not saying that your family will relax (you know them better than I do) but they’re either gonna freak out in the beginning or they won’t, so you might as well be matter-of-fact and sure of yourself in how you present this instead of doing their freaking out for them.

I wish only happy things for you, dear Letter Writer. Please remember: Relationships don’t have to last forever or move toward marriage/kids to be fun or important or worthwhile.

272 thoughts on “#842: “I have a much-older boyfriend who has seven kids. Is my situation ok?”

  1. LW, I have known relationships with greater age differences that have last decades, and included children. I have known relationships with less than a year in age difference that ended in disaster. Remember: it doesn’t have to work for your parents or your friends or other people. It has to work for you and your sweetheart. There are several things to consider about any relationship, and a few that apply even more so to relationships with an age difference. It sounds like you have a good idea of some of those, and the Captain has suggested more things to think about. But if this makes you happy and feels right, and then for a month or a year or decades, I wish you happiness.
    Two notes. Raising kids looks like many different things, and as long as the kids are safe and happy and cared for, having a ‘normal’ family doesn’t matter. Even if the half-sibs are old enough to be the parents. Even if one adult in the household is clearly not a parent. Happy and safe. Second, age-play can be a lot of fun. As long as it doesn’t translate to him using your age against you when you are not playing, enjoy it.

  2. Just wanted to add another question for LW to think about…LW says that when her SO mentions her father he gets starry eyed. But has he actually met her family? It sounds like she has a great relationship with his people but has he expressed an interest in getting to know hers? When two people are contemplating a future together, especially having and raising children, it’s normal to want to know/meet the people your partner comes from. I would be leery of a partner that is fine introducing his family/friends to me….but shows no interest in getting to know mine. Or worse, encourages me to keep our relationship secret from my people.

  3. Excellent advice from the Captain. I want to echo that you can love someone and they can be great for you but they may not be great for you FOREVER.

    My own spouse is quite a bit older than me. I wouldn’t change anything in our relationship, but that age difference is not always easy–things like retirement, illness, and death are things we navigate very differently right now. Just my two cents on that.

    Good luck, LW. Love and hugs to you.

  4. Go slow LW…go slow and the answers will come if you ask the right questions for you. All the hugs, and rock that birth control.

    1. Summs up my reaction perfectly. Go *slow*. Don’t move together/join finances/marry/have children/buy property together. You can be in a very serious relationship for *years* without doing any of that (speaking from lived experience.)

    2. Yes, especially to the birth control. While dating an older man who has children isn’t necessarily a problem (I did, and we’re happy together nearly 30 years later), dating a man who has had three previous relationships is a bit more problematic. Frankly, he’s not a great risk.

    3. This is exactly what I wanted to say. Go slow, go slow, go slow. Especially with anything that makes it significantly harder to split up later–things like merging finances, moving in together, and developing a relationship with his children. (Even if you aren’t in any way responsible for them, if you and he are together long term you will have some kind of relationship with his children, but bonding too fast with a partner’s children is potentially not-good for everyone involved.)

      And I would add that if you feel pressure from him to speed up the timeline, take that as a HUGE red flag.

  5. Being able to articulate his childhood abuse and trace it up to his current issues is really only useful to you if he is able to use that knowledge to improve himself. Right now, he’s kind of just using it as an excuse for how he got into this situation and hasn’t illustrated how he’s going to use that information to develop a stable family unit going forward. And IMO it’s not an especially convincing excuse–it’s a little pat. If he’s just getting bored with his partners or bored with parenting, a rough childhood is convenient as a rationalization that makes him seem like he isn’t at fault or a bad dude. Listen closely when he talks about these things–has he learned lessons? Does he expand on his insight? Or does he bring up his abusive childhood as a way to end the discussion?

    1. Amen. My husband had an abusive childhood and has a colorful marital past (no kids, though). However, he has not once blamed that childhood for any of those failures, and it’s one of the things I love the most about him — that he went through so much and doesn’t use it as an excuse, and doesn’t hate the world for it. In fact, he’s uncomfortable if I point to the fact that I’m not surprised by his romantic past considering what he grew up with seeing in his biological mother. That’s really the key — understanding it as an element of one’s response to the world, and learning how to work with it, not leaning on it as an excuse.

    2. I have to admit, the part about the abuse actually raised a red flag to me. He could be repeating the same relationship patterns; if he grew up in a family with him and 13 other kids from 4 different mothers, and now he has 7 kids from 3 different mothers, he’s already headed down the same path. He could also be using the abusive past as sympathy bait to keep the LW from questioning other aspects of the relationship. And most alarming to me is that there doesn’t seem to be mention of how he got past the abuse he experienced, which makes me wonder if he’ll repeat that pattern and become abusive to the LW later on in the relationship. Why did he break up with the other mothers of his kids? Or did they leave him? It’s not unusual for an abuser to go after one person and treat everyone else wonderfully.

      1. People from abusive backgrounds *do* often recreate patterns, partly because everyone is working from the playbook they were given, and partly because it can be an important part of healing and recovery to re-enact a pattern and have it end *differently*. It’s not fair to label an abusive childhood as a red flag because it’s stigmatizing and something an abused person cannot change, so it implies that abused people are inherently and permanently more dangerous than non-abused people (which isn’t true and therefore isn’t helpful).

        I wouldn’t take his past as a red flag. Pasts just give you context. Use what you know about his past to help you interpret if there are any red flags in his behaviour *now*. The Captain’s advice is excellent.

      2. The sheer number of children this dude has strikes me as a red flag, too, but I have to say, I strongly disagree with you that survivors of abuse tend to become abusers themselves. I know that this does happen sometimes, but what I’ve noticed about the people I’ve interacted with is that although most abusers were once themselves abused, the majority of people who were abused come out of the experience with the desire to never behave that way to anybody. Many of my closest friendships and relationships have been with people who have survived really gross abusive stuff, and it’s because I gravitate toward people who are good at respecting boundaries. When I meet someone who’s really good at hearing a no, who’s really good at making the people around them feel safe, who knows how to not pressure anybody into anything, 99 times out of 100 that person learned those lessons by having their boundaries violated by an abuser.

    3. “This situation” may or may not be worth referring to that way. Yes, it is not a socially acceptable one. But if the kids are all well and happy, love in caring homes, have caring relationships with this man and their other parents, then assuming it’s bad because its nonstandard may be entirely unwarranted. It may be that LW needs to overcome societal prejudices here, or that there are actual red flags.

      I know people with kids from multiple coparents whose children are well loved and in stable living situations. Basically, I think that alone isn’t *necessarily* an actual problem or a situation that would require excuses, and looking at the details and the stability of their homes is far more telling.

  6. I would *personally* be heebed out by that age difference, but LW, you are the master of what does and does not heeb you out. It is not anyone else’s job to be all “dude yuck no” about activity between consenting adults that harms no one.

    I think you just have to keep an eye on that “harms no one” caveat. The reason large age differences heeb me out is that on the advice board where I am a member there is usually at least one post A DAY that goes “I’m a woman in my late teens or early 20s in a relationship with a man 10+ years older than me, it’s amazing and fabulous except for the part where he’s terrifyingly controlling and/or a huge misogynist, how do I get him to stop treating me like an incompetent child?” And the answer is that you can’t because that’s why he is with you, so he can do that crap.

    Which doesn’t mean that all relationships with a big age difference are like that by any means. But it is a thing that is way more likely to happen in relationships with a big age difference, so it’s worth keeping your antenna up.

    1. I like this comment! With the exception that, interesting fact I am sure you super did not know, “heeb” is slang for Jewish; and that was pretty distracting.

      But yeah, other than that I’m with you.

      1. Yeah I’m assuming stellanor is deriving it from “heebie-jeebies” but I’m with you, seeing “heeb” in isolation totally threw me! (; And stellanor, I think you have a great point about how even though large age gaps certainly don’t mean a relationship won’t work, it’s important to acknowledge the power dynamic that is inevitably at play.

        1. I am privileged to hang out with lots of non-bigoted people and live in a very liberal place, so I do sometimes encounter unfortunate slang that I do not know what is (occasionally, awkwardly, even when it is being used to insult me, although my total confusion response just seems to annoy the person so TWO THUMBS UP TO THAT).

          See also: When I was in middle school and didn’t understand why some girl was calling me and several other girls a hoe because I did not in any way resemble a garden tool…

          Which is to say, yes, sorry about that, did not know!

          1. Yeah, the hoe comment confused me for awhile too. And still doesn’t bother me as much as a lot of other insults, because hey, gardening rocks! And brings us food!

      2. Yup, totally did not know that, will stop shortening heebie-jeebies in this way going forward.

        I find my personal creeped-out-alarm generally means THIS HAS A HIGHER THAN AVERAGE LIKELIHOOD OF TURNING OUT POORLY, KEEP YOUR EYES OPEN. Sometimes with more data I can become comfortable. Sometimes with more data I’m like, NOPE, RUN AWAY!

        1. I think we need an onomatopoeic word for stuff that makes you go “Hueeeeeeghk,” but not because of the physical implications. Like “squick.” Emotionally squicky?

          1. “Skeeves” as the verb form of “skeevy”? Looks like it really picked up in usage in the late 70s,

      3. Huh. FWIW, I’m Jewish, I’ve heard of the “heeb” slur, and I didn’t connect it to stellanor’s “heebed” at all until you mentioned it.

      4. and I spend a lot of time there saying check out captainawkward, she is awesome and there was this one post that is similar to your situation etc etc..that and read ‘why doe he do that’ and/or gift of fear.

    2. Is the advice board r/relationships? Because I feel like 75% of the questions are exactly that. “I’m 18 and he’s 45. I love him so much, but he wants me to drop out of high school so I can take care of his kids. What do I do?”

      1. And the other half are “I treat my girlfriend like a sex toy and she doesn’t like it. How can I stop her being so irrational?”

        1. I couldn’t deal with r/relationships after a while. Like, there is no possible answer to most of those questions other than PLEASE PLEASE BREAK UP but you know they won’t. 😦

          1. Ugh, yes, and you just know that when they lead with “breaking up/divorce isn’t an option” in the headline, the body of their question is going to be like “he’s literally the worst person on the entire planet, he hasn’t even tried to get a job in 30 years, does no chores or childcare, and makes sculptures out of beer cans all day, how do I get him to stop”

            You can’t take divorce advice off the table, and then describe a situation to which the only option is divorce. You can’t make your SO change, strangers on reddit DEFINITELY can’t.

          2. It’s like the thing that you see sometimes with advice columns, where someone writes in with “my SO/coworker/roommate is doing X thing that annoys/upsets me. How can I make them stop without having a conversation with them or bringing it up or making it awkward in any way?” I always think, “Uh, I don’t know, become a wizard? Because barring Raistlin-like powers I think you are probably going to have to talk about this, sorry.”

      2. My best friend at 19: “Sure, my 40 year old fiancé is hassling me to drop out of university so I can work full time and support him because he’s screwed up his liver with alcoholism and his health is failing him. Sure he’s not really achieved anything, but you have to remember that all his ex-girlfriends were crazy bitches. Everyone makes sacrifices for love. What are these red flags you keep talking about? I don’t see it. What is a red flag anyway?”

          1. Same here.

            I’m also surprised that there is a CA / reddit overlap in the Venn Diagram of Advice because although I’ve found certain areas of Reddit extremely helpful and supportive (such as Raised by Narcissists), any time the site is mentioned in other feminist spaces I visit, hoards of women tell me how awful it is. But reddit is big. It has loads of areas. Some will be great, some will be awful, depending on your views and wishes. But I’ve never seen a subreddit mentioned positively in a predominantly feminist space before. Which I think can be a shame.

            Anyway – sorry, didn’t mean to derail. This can of course be a conversation for another time and/or place – perhaps I’ll ask about it if you do an AMA! 😉

    3. What squicks me is the combination of age difference and the descriptor, “protective.”

  7. LW, the Captain is right that nothing you’ve said about your partner or the relationship means it CAN’T be happy, successful and good for you. It isn’t automatically sleazy, dodgy or wrong because of any of the details you’ve given us.

    I have been in a similar situation and what eventually ended the relationship was simply the fact that we were at such different stages of our lives and wanted different things. For example: his desire to do outdoor adventures was waning, he was a NO to kids, he had been divorced and didn’t want to marry again. These were questions I hadn’t yet settled, or things I didn’t feel the same about. So just as an example, If you don’t know if you want kids, and it turns out your partner is done having kids, you might find you want different things in the future.

    My ex was 20 years older than me (I was 21 when we started dating) and we had five years together. I feel like the relationship enriched my life and we had some great times I would never wish away. But it ended – and that was ok too.

    In terms of telling your parents, they may well be horrified. Mine were absolutely. But what mellowed them was seeing over time (probably about a year) that my ex was good to me and good for me. Your parents may hate the *idea* of your partner, but over time they could learn to love *him*.

    As a postscript, at 31 I do now look ale what askance at a much older man dating a younger woman, particularly if it’s a pattern. If he has exes his own age and relates well to women as friends and colleagues, those are good signs. Relying on you too much, slagging off his exes and dating decades-younger women is not the sign of a great guy, so as the Cap says, do have a think about those things.

  8. Honestly, what struck me was your catering to your family’s expectations. What if you fell for a man your age who didn’t fit their script for your life? He might have a disability, or be an unambitious/househusband type. How would your family react, and how would you handle that?

    1. Let me get this straight: the LW is a very young woman dating a man a) significantly older than herself, b) with a history of failed relationships and c) who has 7 children, 5 of whom are apparently still young, and what struck you was her being concerned about her parents’ reaction? Seriously?

      To begin with, if you have a loving relationship with your family, it’s perfectly natural that you will want them to preferably love and at the very least accept your partner. That’s not “catering” to their expectations, as in choosing your partner based on what your family expects. Note that the LW didn’t ask if she should break up with this man because her parents will disapprove, she merely asked advice about how to handle the situation as smoothly as possible. Secondly, the LW has herself some very understandable reservations about this relationship, which I suspect would make it harder to stand her ground. It’s one thing to be firm with your parents when you think they are being prejudiced and narrow-minded about your partner, it’s another when they are voicing your own thoughts to you.

      1. Do we know that they are her thoughts, though, or ‘values’ that she’s regurgitating from her parents? I know that in my twenties I made a lot of choices based on what my parents thought was best, or what would cause the least friction in our (my parents and my) relationship. They meant well, but I wanted something different but just hadn’t figured out how to tell them that and deal with the fallout responsibly.

        I get that the Captain and commenters think that there are some caution flags in this relationship, and the LW agrees or she wouldn’t have written in. But that doesn’t mean that it isn’t worthwhile for her to think about whether her parents’ desires for her and her own match up. Hoping that your parents like your partner is not the same thing as only choosing partners that you know they won’t object to even if it’s not what you really want in your heart of hearts.

        1. I think it’s courteous to take the LW at her word that when she says she has certain worries, that she is in fact having those worries in her own head, and is not experiencing parent-induced false consciousness, particularly as she is clear about her parents’ expectations as separate from her own.

      2. No one is saying that this guy is gold star boyfriend and the LW should hang on for all she’s worth. It’s more that being unable to be honest about what the LW wants with her parents is separate problem. There are tons of guys out there who might be a good match for the LW that her parents might disapprove of. The Captain had a good point that she doesn’t owe her parents to live the life that they want for her.

  9. LW mentions that Partner gets starry eyed *mentioning* her dad. But has he actually met her family? It didn’t sound so from the letter. If you’re contemplating a future with this man, I’d be very leery if he never actually wants to meet your family and friends, especially family. It’s incredibly off that LW has such a great relationship with many of his people but seems to spend 0 time with hers. And if Partner is actively encouraging LW to keep the relationship a secret, that’s even weirder and should definitely give LW a lot of pause for thought. Especially if the pair do end up having children…those children will be the product of BOTH family lines. If it’s real love and real commitment, and if you decide you do want a future with this person, he should be expressing some desire to get to know your people, too. Has he? If not, why do you think that is? Are his reasons legit….or do they make you feel not right? Something to think about…

  10. The bit about the best predictor of future behavior is often past behavior is very very true. I’d add my own mantra to that: Keep score by what people do more than by what they say. (and pay attention when the two don’t match up!)

    It’s possible that part of what’s got you feeling conflicted, LW, is that while what you have with this guy is nice, it isn’t what you want. The best seasoned, best prepared, best cooked piece of fried chicken is not sushi. It’s good, but if you’ve got a hankering for sushi, it’s just not what you want.

    People don’t have to be mean, or bad, or cruel to not be right for you. Relationships don’t have to end because one person did something bad to the other; they can end because they’re just not what you want.

    I don’t have an opinion on if the LW should break up with her guy or not, but I’m getting hints from the letter that she’s making some assumptions about relationships that maybe need to be reconsidered.

  11. LW, I’m confused by this: “The youngest five are from one mother and she takes care of them primarily, and BF has emphatically stated they are not my responsibility. A couple come over, I ask about school, let them play my Xbox, give them junk food and they go home. So that’s not really a problem.”

    They come over to your house? To his house? Where is he when you are talking with them about school and giving them junk food? It sounds like, from this phrasing, that you’re kind of watching them. Are you living with your BF? I guess I’d like some clarification about this.

    1. Right, and on top of which, if LW wants a long-term relationship with this man, she will be a stepmother to 7 (5 of whom must be young if they are still in school). That comes with responsibilities, no matter how much BF “emphatically states” otherwise. She won’t just be Dad’s friend with the Xbox, then — she’ll be intimately involved in their lives!

      1. Even the fact that he’s trying to compartmentalize like that is a big red flag for me! What does it mean that he’s in a serious enough relationship that he’s hinting at having kids with LW yet considers his relationship with LW “emphatically” not connected to his responsibilities to his existing children?

      2. Yeah – dating someone with kids does entail some responsibility, even if it’s very clear that you are taking a very secondary role in the kids’ lives. LW, it’s worthwhile thinking through the implications of this in more detail – what if one of the kids got really sick and there were big medical bills or other associated costs? What if something happened to their mom and your partner needed to step up and do more of the primary caregiving? What if one of the kids comes to you to tell you about somethng personal in their lives? It’s not a reason to break up, necessarily, but it’s a thing you should look at head on.

        1. This is the primary reason I, who don’t want kids, don’t want to date anyone with kids: you become at least to some degree a coparent if you get serious. It’s a little like if someone in the household gets a cat or dog, you can say “that’s your pet not mine” all day long but it’s the household’s pet.

          1. People seem to get so angry on online dating sites when people nope out as soon as they learn they have kids. I may want children myself someday, but I know my limits and I’m not prepared right now to date someone who already has kids, regardless of their level of involvement in their kids’ lives. Dating and marrying someone else’s mother or father makes you at least a little bit responsible for their wellbeing. Take my opting out early as a blessing to you and your kids, people! /rant

          2. Yes, this is very important. I’ve never dated someone with kids, but both my parents remarried so I’ve seen the gf / bf /stepparent thing in action. My dad dated plenty before he finally settled down for the second marriage. One of my stepparents is da bomb, the other one is an abusive, narcissistic asshole. Here are some suggestions from a stepkid:

            When it comes to kids, the dating stage is very different from the seriously dating stage, where you are thinking about life-entanglements such as moving in together. When you’re dating, the stepparent is like a cool aunt or uncle – they (usually) are trying to make nice, so they spoil you and don’t give you crap (AKA let you play video games and feed you junk). Kids like that. When you actually step into the parent role, no matter how distantly, the dynamic does change. Particularly if they are young and regularly living in the same house as you (most custody arrangements I’ve experienced have a few of these a month at least – alternating weekends with Wed. visits, for example).

            It’s very important to be clear exactly what your role is regarding his kids, and to observe a) how well behaved they are b) how much control he has over them and c) (this one is huge) what kind of relationship he has with the kids mothers, and how effectively they parent as a unit.

            Obviously, kids are going to be snots sometimes (my sisters and I certainly were, to all parents involved), but that’s a normal part of parenting. But being a steppy is a little different. Will you be allowed to discipline them, or will they basically get to do whatever they want when they are home alone with you? Discipline can be a very fraught subject even between the blood parents of the kids, so it’s really important that everyone’s on the same page and parenting like adults. Also, divorced kids in an unhealthy situation tend to pick up unhealthy behaviors, such as taking advantage of a stepparent’s perceived lack of authority or running back to the parent with the most sympathy when something happens they don’t like. It doesn’t always happen, but in a toxic situation it’s SO MUCH MORE LIKELY to happen. Kids are very good at observing when their parents don’t present a united front, and the more people there are, the more potential weak points they are.

            Keep in mind that by all this I don’t mean to say that divorce and exes and step-parenting are all Horrible things that should be avoided at all costs, because sometimes they work out swimmingly for everyone. My stepmom, as I said above, is Da Bomb. And I’m definitely not saying that your boyfriend is trouble and his kids are nightmares, because for all I know they aren’t. But in my experience this situation has a huge potential for drama. The best thing you can do to protect yourself, OP, is observe how the family functions. And give it enough time that you see how things really work – the surface, sociable aspect of this family’s life may be very different from the *real* side you’d see living in it day to day. That’s true of any family, simple or complex. But everyone’s situation is different, and as the Captain said, we can’t make a statement on your situation. Only you can do that. Best of luck, OP.

          3. Yeah. I love kids, but due to medical issues, I’m not a reliable care provider except in the very short term (I can babysit for two hours, that sort of thing). But I can’t exactly say to an SO who wants kids “we can do that, so long as you do all the hard parts.”

            So I spoil my siblings kids instead, while knowing that I’m always going to have to make it clear that parenting is not in my future.

          4. Speaking as a mom with joint custody of a 12-year old and a 10-year-old, I *WANT* people to Nope on outta there if they’re uninterested or uncomfortable about the prospect of having a significant role in my kids’ lives!!

            I have no problem with people who don’t want children… totally their business; they are the boss of their life, and I am not. But it is a very bad idea for me to date them, for exactly the reasons outlined above: if the relationship gets serious enough for us to do even a pretty mild modicum of life-entwining, well, my kids are the most important things in mine, and anybody I get close enough with that we want to start considering each other family is going to end up family to them too; we’re a package deal.

            That being the case, the absolute last situation I want to find myself in is madly in love with somebody who is madly in love with me, but doesn’t want to be part of a family with children, so we have to break up — mutual shattered hearts and all. SO much easier on everyone involved if I say *right* up front in the profile that I have kids who live with me most of the time and are the joy of my world, and if that successfully cues everybody who is looking for a childfree existence (either temporarily or permanently) to breeze on past me and find somebody more compatible with them; leaving me to find people who are, in turn, more compatible with me. Why would I be upset that someone who’s romantically incompatible with me anyway, on that kind of an irreconcilable level, didn’t start dating me?

            The whole thing is very like the guys who consider it unfair that, because I’m a woman looking for other women, I’ve set my profile to be invisible to men, so they don’t have a chance at me. Seriously, dude? I’m a lesbian. You don’t have a chance at me anyway. We are fundamentally Not Right For Each Other. You don’t wanna waste your time pursuing me — trust me on this. It will avail you naught.

        2. Not just the bigger stuff… just being around as an adult figure in their life makes you responsible. Kids can’t magically pretend an adult doesn’t exist. And even if you try to stay out of child-rearing as a neutral party, the kids will still come to you. Daddy’s not letting them do something while you’re around? They’ll whine or appeal to you to change his mind. They want to do something that they knew Daddy would say “no” to? They’ll ask you first! And you’ll have to do the dance of “did you ask your father/what did your father say?”… even if you’re not “in charge” or even baby-sitting, you’ll be treated as some kind of authority figure by proxy. Always being the good guy giving them candy and video games isn’t feasible long-term, nor is ignoring them. They will form relationships with you, have expectations of you, and you’ll be a part of their lives whether you want to or not (and they’ll be times when your BF needs you to have his back on something.)

          I speak from experience as the child-free 12-years younger sister of a brother with 4 kids. I dislike kids so I stayed out of the way as much as I could when they were young, but after his divorce my brother moved back in with my parents and I was left in the thick of it. I never baby-sat, I never watched them for more than 5-10 minutes, but I still became an authority to them simply by being present in their lives every day. It’s not a web you can be divorced from, even moreso if you’re dating the person with kids.

      3. Something about this guy strikes me as a nice, but lazy dad. Does he do things with his kids that are necessary but not enjoyable for him (taking them to stuff they like and he doesn’t/supervising them like an actual adult)? Or does he rely on the kids to manage themselves? Do the kids look after each other more than he looks after them?

        I know he says the kids are his responsibility, but sometimes people just say what they want others to hear. Maybe reenactments of the Lord of the Flies doesn’t bother him, so he doesn’t think you need to step in to stop his kids from going off unsupervised while they vandalize stuff (based off of many true stories).

      4. Good eye, because if she’s as detached from his family as Dad wants her to be, what does that mean- that she’s just his non-reproducing playtoy he escapes his parenting responsibilities with?

        1. Having this be a “semi-secret relationship” which both parties are finding stimulating and have reasons to enforce, kinda goes along with my idea.

          Re the age-dependent hazing- LW, see if you find “People joke about their truths,” as useful as I do. Best wishes though, you are the only one who gets to decide what will make you happy.

        2. Hmm, you seem to be implying that it’s a bad thing to have a fun sexual relationship with someone who’s not involved with your children in a caretaker-y way. Did I get that right? If so, I have a thing to say:

          I’m in a friendship-with-benefits with someone which has a very playful feel to it, and I do think that that’s part of the appeal for him — his life is pretty high-stress right now, and he seems to really like to get away from it all and hang out with someone who’s a little outside it, who’s not super connected to the more serious/responsible parts of his life. He’s a wonderful parent (a largely stay-at-home dad, actually) and his daughter is always in good hands while he’s not with her. I think it’s healthy for him to get a break from serious stuff now and then, and our arrangement suits us both really well. (I should mention that we’re both poly. His baby-mama and his other partners know about us and are fine with it, as are mine.)

          My point is that it’s not necessarily bad or unhealthy to have a relationship that’s fun and playful and where you can get a temporary escape now and then from your parenting responsibilities. So long as you’re making sure the kids are taken care of while you’re not with them, that actually sounds like it could be a really healthy thing to have in your life, as it seems to be for my fwb.

          It’s also possible that you were intending to point out that this type of compartmentalized relationship can realistically only get so intimate, and that it might not be what LW wants for that reason. I’ll agree that a parent who’s heavily involved with their children’s lives can only give so much to a partner who’s not interested in being involved with the kids. I can’t tell from her letter what the LW wants, how much intimacy she’s hoping for with this dude or what she wants their relationship to look like. LW, good luck, and I hope you can figure out something that works for you both.

          (Also, I didn’t interpret the dude’s statement that the LW wasn’t responsible for the kids as him wanting to keep her separate from them — more as him trying to make sure she knows he doesn’t expect her to be their stepmom just because she’s dating him.)

          1. Right, except that in this letter she seems to be working through evaluating him as a potential life partner. If she decides she’d rather just keep it casual, and he agrees, then they’re golden, but I don’t think she’s decided that — she’s considering marrying him and reproducing with him herself. If she wants either of those things, then maybe this is a warning.

      5. I think this is one situation where sitting down and seriously considering worst-case scenarios is a wise move. BF can say whatever he wants, but if LW marries him, she’s going to be responsible in some sense-and if their mom dies or is no longer able to care for the kids, she’s going to have a boatload of unplanned responsibility. And yes it’s morbid, but it also happens.

        1. Yeah, I think there was a letter here a while back on a similar topic–LW, if you marry this guy, you become those kids’ stepmother. If he has a relationship with them, then you do too. There’s really no way around that, at least not if the kids in question are *children*.

        2. Absolutely happens. A former coworker of mine was a noncustodial parent to her two kids, and then her ex-husband died very suddenly — she wound up having to suddenly take over full-time not just with her own daughters, but with two other children as well that he’d had whose own mothers weren’t involved.

          She wound up taking a three-month leave of absence from work because trying to get his affairs in order, taking care of the girls, and then *moving* because a one-bedroom was not adequate for five people — it was all too much for her to do while trying to keep any kind of steady work. She’s moved on, and I’ve got all confidence that she’s a great mom/stepmom, but it’s a hell of a cautionary tale about the ways life likes to look at your plans and laugh maniacally just before sweeping them all into shards.

    2. This quote also makes me a little confused about how serious or long-standing their relationship is. It’s serious enough that she’s been introduced to his children, including school age ones, so that seems pretty serious. And she is hanging out with them enough that their dad even thought he needed to tell her they aren’t her ‘responsibility’?? Why would it even occur to her that they would be her responsibility if they’re just dating? And if they are serious enough to be living together and for her to start naturally slipping into a familial role with them… then how can he expect that to work without them forming some kind of family bond, and how well is he actually providing a stable place for them?

      It does sound like they don’t live with him, only sometimes visit, but it also sounds a little like he’s brushing off his own children as people whose emotional needs don’t need to be considered?

      It’s all just kind of confusing.

      1. If you’re entering into a new relationship when you have children, it’s generally a good idea to reassure the person you’re dating that you’re not asking them to step into the role of step-parent before they feel ready to do so (if they ever do at all).

      2. If I am reading LW’s signoff correctly, they have been dating for a year. If it had been a year and she hadn’t at least seen his kids, I would be just as worried.

        But yes on thinking about how he parents and using that information. It is important data to consider.

        1. True, a year is a while…

          I guess what I’m getting at is what is her role right now in these kids’ lives, especially the younger ones? How old are they even (and why wasn’t that important enough to mention?) How much time do they spend around her? How much of the time they’re with their dad is she there too? How much time do they spend with their dad (and if the answer is they’re mostly with their mom instead of him, why?) What have they been told about this relationship and what discussions have been had? What role does she imagine having in their lives in the future? What role does their dad imagine her having? (And even more fundamentally, what kind of a father is he?).

          I guess some of her comments about the kids made me wonder if she was reassuring herself (or worse, he was reassuring her) that they wouldn’t make too much difference in the long run? Which is really even more worrying to me than the opposite. It makes me question the dad.

          Obviously there may be reasonable answers to every one of these questions! But the kids inspire so many questions in me…

        2. True, a year is a while…

          I guess what I’m getting at is what is her role right now in these kids’ lives, especially the younger ones? How old are they even (and why wasn’t that important enough to mention?) How much time do they spend around her? How much of the time they’re with their dad is she there too? How much time do they spend with their dad (and if the answer is they’re mostly with their mom instead of him, why?) What have they been told about this relationship and what discussions have been had? What role does she imagine having in their lives in the future? What role does their dad imagine her having? (And even more fundamentally, what kind of a father is he?).

          I guess some of her comments about the kids made me wonder if she was reassuring herself (or worse, he was reassuring her) that they wouldn’t make too much difference in the long run? Which is really even more worrying to me than the opposite. It makes me question the dad.

          Obviously there may be reasonable answers to every one of these questions! But the kids inspire so many questions in me…

        3. Eh, I dated my current partner for 18 months before he met my daughter. She bonds with people really quickly, so we wanted (and were suited to) to be sure that we wanted something long-term and serious before that happened.

          I can see how not meeting them could be a red flag, I just think that meeting too soon is more likely to be a problem than the opposite.

    3. I wondered those things, also, and especially the part where the kids are supposed to be the ex’s responsibility, not LW’s. If this man’s parenting plan is letting his girlfriend babysit his kids and feed them junk food during his custody time, then having the ex take care of them the rest of the time, color me not impressed.

    4. “Semi-secret” + “instant connection” + “‘his eldest child even gave me gift ideas for [BF’s] birthday the first time I met her'” -these are people who want you to become entwined before others can comment. Aside from all else, we enjoy so many social rituals acknowledging our connections to others. Why does using their playbook mean you’re expected to skip over all that?

      1. I wondered, how does *he* feel about the semi-secret aspect? I’d I were him, that would be something I’d have talked by this point I think about how can we go public fairly soon. Does he just not care? Does he have any motivation to keep it this way?

  12. “It took a while for me to put aside my prejudice and accept that he came from an abusive, broken family (13 siblings from 4 different mothers).”

    This line is very interesting and gave me pause. I can’t tell if the assumption is 1) that the only good reason somebody might have seven children with three different partners is because they came from an abusive broken family or 2) that you have seen patterns of behavior that hint that those partnerships failed because of toxic behaviors he learned from his family of origin (I’m presuming in both cases that he has disclosed that his family of origin was abusive).

    In the case of 1), I would say, I understand that assumption. If I were dating somebody who had three former partners they were still connected to via children, I might be a little wary. But I’m not convinced that it is necessarily an indication of abusive dynamics unless there are other reasons to think so; my sister-in-law has children from three different partners, and though I don’t agree with all of her life choices, I would hate to think that somebody is writing her off JUST based on her history.

    In the case of 2), I think other commenters and the Captain have touched on why that could be a problem and what you could do to suss out how you want to move forward. Really, my thinking is the children by multiple partners and age difference are not, in of themselves, symptoms of an unhealthy relationship. However, large age differences include a power dynamic that it’s good to be aware of (again, other commenters will have more to say about this).

    It sounds like the content of the relationship thus far has been really positive, and for that, I am happy! I hope you are able to enjoy this relationship for the best that it has to offer, and that writing in to the Captain has given you some clarity for moving forward in a way that feels safe and constructive to you.

  13. I fell in love with a man in his 40s when I was in my 20s. It did not go well. There is no way to tell how your relationship will pan out until you live it, but what you can do is take things slowly, be cautious, and pay attention to red flags. His words and actions need to match. Does he participate meaningfully in his kids’ lives? Does he have a civil relationship with their moms? Is ‘protective’ a euphemism for ‘controlling’? He has a history of rushing into marriage and kids, so make sure you are the one setting the pace.

      1. Yeah, ‘protective’ always makes me very nervous and suspicious. It’s got quite a different feel to it from ‘I know he’s always got my back’, for example.

        1. Same here, I think because there is a rather unequal vibe to it. It also seems to me like it’s often men who are “protective” and it’s seen as good/manly/chivalrous etc but women are “overprotective” and it’s smothering/bad/irrational.

      2. Same. I’m deeply leery of dudes who’ve got their girlfriends or wives describing them as “protective” and thinking it’s a good thing. Just based on experience. But “protective” was probably the ruddiest flag in the letter, for me.

      3. In my experience (and, to my shame, twice on my part), that is literally always the case. I have never, ever seen anyone described as “protective” where that wasn’t a euphemism for “controlling” or “authoritarian”, and most times with a patriarchial dynamic. Squick.

        1. I made the mistake of keeping in touch with an ex, and when I passingly mentioned going out with a friend and meeting some fun guys who I had a great conversation with, he got weirdly stern. When pressed, he said, “Oh, I just worry. I don’t want you to get hurt. Maybe it’s a kind of older brother instinct.”
          He couldn’t figure out why I was so angry at him. Why yes, man who I had sex with and who is exactly the same age as me, go ahead and compare yourself to a family member, with the implication that I need an older male to screen my dates for me.

      4. Adding in the age difference as well gives it a whole new level of potential ickiness.

    1. On the flip side, there was a 20 year age difference between my dad and mom, and he had two kids from a previous marriage. But his words and actions matched: he was still on good terms with his ex – they weren’t BFFs, but for example, she couldn’t drive, and every now and then would get stranded somewhere due to bus/ride cancellations, etc, and could count on him to come pick her up if she needed it – and he had joint custody of my older sibs and was very involved as a parent.

      On paper, he didn’t fit the profile of what my mother’s parents wanted for her partner – but he *was* actually a good dude, which was demonstrated through all of the above, and they eventually came around. It was universally agreed that the age difference was weird and awkward (and that my mom was a step-mom to kids who were only 10 years younger than she was) but it was a great partnership for 37 years (until my mom passed away).

      So having that great relationship despite the age gap is possible. But *definitely* look at his other relationships – how he interacts with his exes, how he talks about them (does he act like they were all over dramatic and he was faultless in the break ups? that’s … a lot of relationships coincidentally ending the same way…), and how they talk about him, and how he interacts with his kids. If you find yourself with creeping doubts or noticing red flags, pay attention to those things and bail.

    2. When I was seventeen a friend of mine was seeing a 42-year-old. He had a daughter who was 25, an ex-wife his own age, and lived with a girlfriend who was around thirty. Basically, every ten years or so he found a younger model.

      He left the girlfriend to be with my friend, gave up his job and moved cities to be with her. Finally he’d found the right one! True love for ever! She finished her degree, and then said, “well, this has been fun but I’m 22 and my career is incredibly important and I’m moving to live abroad now. Catch you later!” He could. Not. Cope.

      This is not especially relevant, but twenty years later I still love how effectively my friend flipped the script. I was very dubious about it at the time, but now I think she was amazing. She’d never wanted kids and was very passionate about her work and her career, and as a very, very focused and savvy seventeen-year-old had made the decision that this relationship worked for her perfectly well, and enjoyed having an older boyfriend with a bit more money and not having to deal with the dramas of university relationships, without any illusions about it lasting 4-eva or anything.

      Anyway, LW, the point is, keep checking in with yourself to make sure that this relationship is working FOR YOU. Don’t make any irrevocable decisions. Keep thinking about what you want long-term and whether this fits in. Pay attention if there is a little bit of you going, “huh, um, what you just said made me kind of uncomfortable?” There are no right or wrong answers about whether this relationship is right for you or wrong for you, but you are asking some perfectly sensible questions and it’s ok not to know the answers right away and to take things slowly until you do know the answers.

    3. “Is ‘protective’ a euphemism for ‘controlling’?”

      Guys being referred to as protective tends to make me wonder exactly what he’s supposed to be protecting her from. Or who.

    4. I always end up wondering exactly what he’s supposed to be protecting her from. Raging tigers? An influx of army ants? Bad traffic signals? Cranky spaniels who object to being removed from rocking chairs?

      1. Ha! I need to remember these examples so I can use them if anyone tries the “protective” act on me. 😀 😀 😀

  14. “Relationships don’t have to last forever or move toward marriage/kids to be fun or important or worthwhile.”

    I wish it hadn’t taken me so long to internalize this. I nursed a broken heart for 20 years before finally realizing that I should have been celebrating the love we shared for a few years while going on with my life. A friend told me, “Hearts are meant to be broken. Let yours heal and love again.”

    1. One of my favorite poems, which really helped me, was Failing and Flying by Jack Gilbert, which starts “Everyone forgets that Icarus also flew.” and ends “I believe Icarus was not failing as he fell,/but just coming to the end of his triumph.” (it’s easily googable to get the entire thing in a legal form, but I think linking will get me in the spam filter?)

  15. Please also think ahead financially. Child support for seven kids is a lot of money, and it is very possible in a few years you will really resent not being able to buy a pair of shoes for your own kid because all the money is going to his earlier kids.

    1. That’s a good point – “emphatically stating” that the kids aren’t LW’s responsibility doesn’t make them any less her responsibility if they joined finances! If LW is at the point of thinking about possibly having children with this man, she should also be reassessing the role she’ll be playing in these kids’ lives, especially the ones of school age. Just something else to pay a lot of attention to when/if she interacts at all (or sees BF interacting with) the other ex-wives, especially the ones who came into the picture as stepmothers.

    2. Yeah I was thinking this. Or in the future you always have to keep your money separate because of issues with his finances and child support. And you can’t buy a house, or are worried that your salary finances all your joint living expenses because his finances previous children. Or you can’t get married because he hasn’t paid child support and his credit is a mess. Even if he isn’t paying child support now, that can change with one court order that includes back support.

      1. Or, he dies and LW’s caretaking role (and house, finances, 401k) is now seen by courts or a lawyer as part of the minor children’s support.

        A friend of mine had a relationship with a guy with kids, and when they broke up, she said the loss of the kids was harder on her than ending it with the guy had been.

    3. Not to mention attorney fees if things go really sour with one of his exes. Custody & child support modifications are expensive and hideously stressful.

    4. I used to moderate a listserv for people in age gap relationships, and one of the most frequent things young women in relationships with older men with kids wrote for advice about was that they wanted to have a child and their husband said he couldn’t afford it. Most of them displaced the blame about the squashing of their dreams of motherhood on the stepchildren and the ex-wife (usually I think because it wasn’t actually safe to be angry with their husband), but this is definitely a thing that you need to prepare for. Marrying this dude would mean that LW would end up contributing to child support, contributing to legal fees for changes in support or custody orders, etc, which doesn’t sound to me like “not being responsible for his kids”.

  16. As someone in a stable enduring relationship with a man 30 years older (it’s now been about 6 years total, 4 of them living together), I would like to echo Captain Awkward’s questions, as well as concerns about power dynamics in the relationship as raised by other commentators as well. Me and my partner have lasted because we are extremely aware of these questions and our answers to them.

    We keep track of potential changes to these answers – that is, we keep having these conversations, on and off, when it seems relevant. For example, we discussed and agree that this relationship works very well in terms of overall compatibility and stability in day-to-day matters – a consideration that over-rides chemistry by significant margin. It always makes sense to be aware of how your differences help things and how they complicate things. Age differences seem to add extra layers to these considerations that are important to explore, both in the beginning and as the relationship continues to evolve.

    As part of these questions, we also talked about “This is great now – but what happens in 30 years?”. We discussed our hopes and our fears, life and career stages, expectations, etc. And while we have not made exhaustive plans, we have an idea of how to handle the differences and fears, both immediate and in the future.

    Given that others here have mentioned chemistry as a strong factor, I wanted to add the following. For me, there was even a noticeable period of time when “hotness” and level of desire from my side had seriously fallen due to other stressors, and I contemplated what happens if it never returns. And at that point, I decided that the relationship still worked wonderfully enough to be worth it. I am happy to say that my sexual drive rebounded, yet this period was an important test for both of us.

    Lastly, despite many years together and complete acceptance from my family, the age difference still occasionally makes me uneasy in public settings. But I decided that I can deal with this unease, acknowledge it, monitor it, sometimes stay with it, sometimes confront it, etc. – just like I deal with other tricks my brain likes to play. My anxiety circulates in and out of diagnostic threshold, and I had experience with social anxiety in the past, so I am treating this unease as another subset of it.

  17. LW, you are the boss of you and you are the only one who knows what’s right. I am 11 years older than my partner, which freaked me out a ton at first. However, we have kids the same age (I had them late, he had his early), we co-parent brilliantly, and 6 years later, I hardly ever think about the age difference. But we did not get serious together for a LONG TIME and we did not involve our kids in our relationship for a LONG TIME. Take it slow, ask the questions, read the signs. You’ll make the right decision for you!

  18. Take your time and use mulitple forms of birth control, and use them reliably.

    Beyond that, have fun…

    1. I second this, strongly. This dude is FERTILE.

      What is his relationship like with the mothers of his children ? Is he currently paying child support for any/all of them ? This will reveal a great deal about what you need to know about him in the future with you.

  19. Adding to “Does he date or has he dated women his own age?” I would add: “How old were the mothers of his children when he was with them, and when they parted?” It would raise a huge red flag to me if he had a pattern of dating women in their early or mid-20s and breaking up with them, say, when they hit 30.

    1. That is precisely the pattern I would watch out for, too. It is very possible that it isn’t what’s going on here, but I have sadly known a number of guys who had a patten of dumping their partners when they get “too old” (30-35, usually). In a couple of cases it was clear that when they complimented a new girlfriend on being special and magical and exciting, what they meant was “young,” and the “magic” wore off pretty quick when she inevitably aged.

      Again, might not be going on here! But it’s something I’d keep a weather eye out for.

      1. Heehee I wish I’d said that to all the 40 and 50 something men who were after me when I was in my 20s! 🙂

      2. Because blah blah blah evopsych hip-to-waist ratios it’s all science blah blah blah old women are icky.

  20. You will also end up with some kind of interaction with the mother of his five children. Particularly challenging if you don’t come from a background of a broken home. Challenging either way.

  21. “Telling my family. I CAN’T.”

    Until you are able to own your decisions in the face of your family’s possible surprise and/or disapproval, you are not ready to commit to this. It’s really hard to learn how to be your own person when you have always been the person your parents expected you to be. In some ways, this is harder if you weren’t forcing yourself to be their idea of what you should be, but it just kind of happened because the things you wanted happened to line up with their expectations.

    If they wanted a quiet kid who did well in school, and you happen to be an introvert who loves school, then, with no malice on anyone’s part, you avoided the part of growing up where you had to learn to be steadfastly yourself in the face of parental disappointment or disapproval. And if you have carved out little areas of difference, it sounds like you’ve done them in places where you don’t have to do it way out loud and in their faces. Like, you can be an atheist and they can be unhappy about it, but if you show up for holidays and politely attend church with them or bow your head when they recite grace before meals, then everyone can pretend it’s no big deal.

    But if you marry someone they don’t approve of, they will not be able to pretend it’s anything other than what it is. So maybe while you are figuring out if this is the guy for you, you could also work on differentiating yourself more clearly from your parents’ expectations. If you quietly go to church with them on Christmas Eve, stop doing that. If you don’t ever tell them when you disagree with them politically, try the experiment of actually speaking up. Tell them things about yourself that you suspect will surprise them. If you do decide to marry this man, you will need to be able to be strong and steady in the face of their reactions, and practicing being who you are (instead of letting them think you are closer to who they wish you were than you actually may be) is a good way to build that skill. And the upside is that you will most likely learn that after a period of adjustment, they actually can and will love you just because you are you, even if you didn’t turn out to be the exact person they may have imagined when they first help you in their arms.

  22. I don’t think any one of the the factors at play here is necessarily a deal breakers on its own, but when they start piling up like this–he’s much older than you AND has multiple failed relationships AND has seven children from different mothers AND one of them is nearly your age AND you work together AND your relationship is semi-secret–well, that’s a lot of ANDs.

    LW, you are 25. The whole world of people and relationships is wide open to you. You don’t have to take on this guy’s gigantic rolling cart full of baggage just because he’s gentle and witty–and I say that as someone who is around his age and has a pretty heavily laden baggage cart of her own. You’re an adult and ultimately it’s up to you, but I really hope you’ll take the last line of the Captain’s advice to heart, and enjoy your time with him for what it is without getting entangled forever.

  23. My experience with people that have more than six children was that they were in (tight) friend groups only with others who came from large families and or had large families themselves. And it’s not even a group of people with the same religious beliefs. Being childless did make me the weirdo. Despite their initial charisma, the requirement for membership was too high for me.

  24. As usual, Captain Awkward has a wonderful response that covers all bases.

    I am a 29yo happily married to a 53yo who has a 22yo son. We’ve been together for several years now. He looked younger, I looked older, and he was supposed to be a lost weekend/6-week fling kinda thing, so we didn’t really ask about ages when we started banging. And then we actually started enjoying each other in non-sexual ways, and learning about each other, and it was like “Holy shit, this is weird! Do we still do this? Are there unresolved Daddy issues I wasn’t aware of? Is he being a creep? Am *I* being a creep” We actually ended up taking a break of several weeks to process our feelings over the whole thing.

    LW, I had *such* reservations about starting to actually date this guy, let alone getting serious with him. He had *such* reservations about getting serious with me (big point in his favor, BTW). Literally the only reason we were able to proceed in a non-skeevy way (and the reason he is/was well liked by my family, including my very cynical and judgy grandparents) was that he demonstrated that he was not someone who was just creeping on a younger girl. His previous relationships were with women much closer to his age, and he is still close friends (in an appropriate and non-sexual kinda way) with many of them.

    Even though things are pretty harmonious, there have been many, many times over the years where the age difference has caused us some conflict. Sometimes he has a tendancy to be a little heavy on the advice giving, which would be annoying from anyone, but can also feel paternalistic to me because of the age difference. Along those lines, I am sometimes very whiny and lazy, and it makes him feel gross if he has to “remind me to do my chores” or something. We’ve had to be very open and honest about the weirdness, and now we both strive to stamp that shit out immediately. I also identify with your concerns about age play, because we are also prone to playful spanking and threats thereof. Again, we have had to openly talk about the weirdness. There are also the practical considerations of building a life with someone who is in a different stage of life, which can make it difficult sometimes to make joint decisions that work for both of us.

    So, it can work, but you both have to have earnest, frequently uncomfortable discussions, and you best keep your eyes wide open.

  25. LW, I have been with a complicated man 8 years my senior since I was 19 for nearly 12 years now, and here are the things I wish I’d been told that may be relevant to your situation.

    1. In your 20s you are a constantly evolving creature. This is the best and worst thing about being young. By your 30s you settle into yourself. This leads to a more secure sense of self and self acceptance, BUT this also means that some habits, tendencies, etc. become less malleable. For habits that are maladaptive, like relationship styles learned from abusive households, it can be harder to unlearn them without intensive effort (e.g. ongoing therapy). I’ve seen my husband go through this as someone who is very motivated to not become his parents but has to fight the tendency to do so often.

    2. As I’ve gotten older I’ve gotten much better at evaluating partners who have unresolved baggage or bad relationship habits that I would now view as deal breakers. I was not good at spotting them in my 20s because I didn’t have the life experience to know my own deal breakers so well. As the Captain pointed out the factors that are a small issue for you now may become Big Issues for you in 3, 4, 5 years – having kids, financial stability, health concerns with an older partner, etc. This guy already has three failed relationships with the mothers of his children – are they also much younger? Has he had any successful relationships with same-age peers? There may be good reason why he is dating someone with so much less experience, even if it’s not in an intentionally malicious way (e.g. they are more likely to overlook “protective” behavior that is actually controlling – not saying this is the case, just an example).

    For me personally, if I was dating the OP’s partner in an alternate universe, my requirements would be that they have actively worked on the issues stemming from their abusive household in therapy, in the past and ideally present as well. They would be able to articulate how they contributed to the failure of the relationships with the three mothers of their children in a fair and realistic way, with a concrete plan for how to avoid those mistakes going forward. They would be transparent about the financial impact of child support for 7 children on what kind of lifestyle the OP should expect, e.g. whether they plan to work past retirement age or expect OP’s income to help compensate if they merge households down the line. They would also be willing to have a pragmatic (not romantic “I want to make babies with you because lurrrv”) conversation about what role the OP will play as possible step-parent and what is/isn’t on the table in terms of future children.

    I will also reiterate that you can have a great relationship with someone that doesn’t grow into a life partnership because you’re in different places in your lives, careers, reproductive plans, etc. Being in love in years 1-3 and running a household together in year 10+ look and feel very, very different from each other. Someone who has so much inherent complication in his personal life may not be a partner who can handle complication you may bring to the table, e.g. if you get sick, want to move or change jobs, or have a kid. So things might be great when you are young and “uncomplicated” but you need to know what happens if that changes, because it almost definitely will.

  26. LW, any one of the things you’ve mentioned is not cause for concern on its own. Even the whole, when taken in full context and with your own understanding of the complexities around it, could be totally fine. But it’s also a good and normal and healthy thing for you to worry, and it *is* possible that this could turn out to be a squicky situation.

    I would pay attention to some of the sideline things – the details. As those tend to be what raises red flags, for me.

    For example: You mention that you are just casually dating, and you’ve been assured that the 7 children by prior women will not be your responsibility at any point, and even that the mother is the primary care-giver of the younger ones. And yet, you have them at your house? Feeding them snacks and playing games? The first major question that jumps out to me about that is: Does the mother of those kids know about this? Has she met you? Is she aware that you watch them sometimes? It seems odd to me, because in my experience when kids live with Parent A and have *visits* with Parent B, the expectation is that Parent B will spend that visit time *with the children*. And it’s generally a worrying sign if Parent B is handing their kids off to another person – especially someone they’re just dating – on any kind of regular basis.

    1. I assumed she was at his house while the kids were visiting. Which does mean he’s not giving the kids his undivided attention, rather than saying “can’t see you this weekend, spending time with my kids”, but isn’t as entwined as having them at her house.

    2. Indeed. I have seen too many relationships where Parent 1 fights for custody just to make life difficult for Parent 2, or to reduce what they pay in child support, then shoves the kids off on whoever will take them when it’s their turn to parent.

    3. I interpreted that part of the letter very differently: I figured the kids were coming over to dad’s house, while the LW is there, so she hangs out with them because they’re in the same space.

      1. It was the “my Xbox” that made me think it was her house or they were living together already. I guess there’s no reason why her gaming system couldn’t be at his house, but still.

      2. They are coming to LW’s house: “A couple come over, I ask about school, let them play my Xbox, give them junk food and they go home.” Whether or not BF is there while they are is up in the air.

  27. LW, only you can decide if this relationship is right for you. I would be wary of the fact that he already has 7 children by 3 different women – for many reasons, but mostly because, and this is just how I roll, I wouldn’t be comfortable with being so limited in where we can live, how much money we have (because of the serious child support I’m sure he is paying … hopefully) and because I wouldn’t feel comfortable with my kids being 8, 9, and 10.

    That’s just my .02, though.

    1. This. I feel like there’s a lot of pressure (for women especially) to be “open-minded”, and not have too many deal-breakers, and to just give all the potential partners in your dating pool a chance, etc. Objectively speaking, there’s nothing wrong with large families. Objectively speaking, there’s nothing wrong with half-siblings. Seven children by three different women does not automatically make this man a bad person. (Though as others have pointed out, it might be worth digging a little deeper into the circumstances.)

      However, if you consider having your own kids with him, think long and hard about whether you want them to be 8, 9, and 10, as Temperance said. He could very well be an awesome father, who is physically, emotionally, and financially there for the existing seven, and he could be just as awesome in the same ways for any kids you had together. But, after thinking about it long and hard, you decide that’s not something you want to risk with your own kids, that does not make you a bad person at all. Everyone’s allowed to be a little bit selfish (or even a lot) when it comes to choosing their partners. And not like you need a “good” reason to break up (if you choose to one day), but that is a pretty good one.

    2. I agree with your point.

      The already existing seven children are a serious barrier to LW’s future children, seems to me. People of great wealth do this routinely, but if finances are not unlimited, and time never is, the quality of any future children’s upbringing is a real issue to consider. The existing children, in the minds of their mothers and also in the eyes of the law, take precedence.

      And that’s a lot of precedence.

      Large and happy blended families do exist, but everyone involved has to want that to happen. One un-cooperative parent, or one child with extra needs, and the stress is that much harder to deal with.

  28. LW, I’m pretty torn about whether your underlying question is, “he’s perfect, so why do I dislike all these unimportant things about him?” and “he’s really imperfect, so why do I still want to stay with him so much?” Let me say at the outset: you CAN break up with a perfect person; you CAN stay with an imperfect person.

    I actually think you’re asking both of these questions. I think you’ve layered a million zillion narratives onto the relationship so it’s making it difficult for you to see it clearly. The secret relationship, the edgy chemistry, the kinky ageplay, the sexy transgression, the damaged man who can be healed by you and your family, but on the other hand the star-crossed love where your family can never know.

    The Sound of Music vibes, where you get to bang a sexy dude who’s a really terrible father, and be the Maria to his kids.

    Hopefully that’s not too harsh. I just mean: I think there’s a lot going on here, that’s making it really difficult to see your relationship clearly, and it’s hard to know where “people don’t like my relationship because it’s culturally iffy” ends and “people don’t like my relationship because they see something bad that I don’t see” begins. I think the Captain’s questions are perfect for starting to break through those narratives.

    It’s ok to break up with this guy. It’s ok to break up with him because you can’t handle what he’s like right now, even if you think it’s because of a troubled childhood. It’s ok to want to do ageplay with your partner, though I might suggest confining it at first to defined times, since those dynamics do not make for a stunningly healthy relationship. It’s ok to treat this relationship as a time for discovery and not forever.

    You’ll land where you land, and may change your mind,

  29. The age difference, by itself, isn’t necessarily bad. My partner is 21 years older than me, and yes, he was divorced and the father of three teenagers when I met him. BUT… I was a lot older than you when I met him, he’d only been married the one time, and I never felt I had to hide my relationship.
    I’m not sure why your family’s religion is necessarily a barrier, unless it’s a religion that is adamantly against divorce. He is divorced, right? Not just “separated”?
    Personally, I think the three previous relationships are more of a possible red flag than the age difference. Was he married to each, or did they just have children together?
    One divorce – the marriage could have been a youthful mistake.
    Two divorces – the second marriage could have been a rebound mistake, but it’s a bit risky.
    Three (or more) divorces – now you’re getting into risky territory. This is, quite possibly, a person who can’t maintain a relationship for any length of time at all.
    I agree with the comments mentioning birth control. Whatever you do, do not have a baby with this man until you’re absolutely sure of him. Frankly, I don’t see him as a great long term candidate.

  30. LW…what worries me is your list of concerns. There are only 4 on the list but dang, it’s a heavy list. Your family, his family, your yet-to-be kids, and the gaping chasm of your age…those are BIG issues. Honestly, if I wasn’t able to comfortably share my love for someone with my family it would immediately make me rethink my relationship. You’re not saying your parents are hateful people, just that they’d be really uncomfortable with the age difference. You then later mention that you, yourself, are uncomfortable with the age difference. Obviously, it’s a bigger issue than I think you’d like to admit to.

    Here’s the thing. My mother was 17 when she met my father. My father was 34. Those 17 years were HUGE. He was 6 years younger than her mother, 7 years younger than her father, had been married and divorced, had three kids, been in the armed services. In essence he’d lived her entire lifetime (twice!) while she was busy being born and growing up. Their marriage didn’t last (for reasons that went beyond their age difference) but I remember all too well listening to my grandparents lament that she’d been forced to grow up too soon by a man old enough to know better. Two kids (my sister and I) were part of that growing up!

    Nobody gets to make decisions on how to live your life other than you, but be careful.

    1. Yes. I’ve got bad experiences with relationships I didn’t want to tell the people I’m close to about. Something was off.

      1. I would say, as a general rule of thumb, if you do not want to tell the people who matter to you about a certain relationship, there is a reason.

        If it is a good reason, like “my racist parents will be jerks to my new partner,” it makes sense that you do not want to tell them. If you are not able to articulate a reason, chances are it is your gut/intuition telling you something you are not ready to acknowledge yet, which could be a red flag. Only you can know!

        My general mode of operation is that I only want to form relationships with people I am happy to know – people who are great and decent and help me become a better person every day. I do not want to form relationships with people who are not decent (liars, thieves, abusers, etc.) nor with people who bring out the worst in me. Life is too short.

  31. As the third wife of a man ten years older, who had a kid with each of the previous wives, one of whom had the boy live with her and one of whom had lost custody of the child and we raised her…

    You have no idea how complicated this can become. Because I certainly did not. I was 21.

    My husband had learned a lot from these disasters, and I was more mature than both of his exes put together. We managed to make it work. But it was flippin’ hard, constantly, and we had stresses that the usual couple does not ever have to contemplate.

    Both of his exes were crazy in different ways. The first one, the one who lost custody, was a screaming psychopath. She would breeze in, manipulate the heck out of our vulnerable daughter, create uber-drama, and then vanish again. The poor kid was Mommy-starved and would put up with anything. We also could not get her to understand what was going on. We lost touch for a while when BirthMom convinced her to dis-invite her father from her wedding, on the basis that BirthMom was going to pay for “the dream wedding I never had.” Only two weeks before the big event BirthMom announced that “it slipped my mind that I’m pregnant and my husband is out of work, we don’t have a spare dime.”

    Second ex had self-esteem issues. I felt sorry for her because in her own baby book she was referred to as “So-and-so’s little sister.” Terribly insecure, she “loved” her son by getting him a lot of unnecessary medical treatment. When I took them out to fly kites and he broke his arm because she hadn’t told us she had put totally pointless orthotics in his shoes, we went to court and made her have to run any non-emergency medical through his father. Didn’t always work.

    Kids are expensive. And we were only dealing with two of them. Of course it didn’t help that the exes were constantly dragging us to court and stirring up trouble with the poor kids’ heads. Don’t think you won’t get attached and involved. This is what the future holds.

    Speaking of which, your own kids: That is going to be different. Very very different from anything you imagined. Because no one wants to picture, as the commenter above mentioned, “my kids being [numbers] 8, 9, and 10.” Now if your BF were independently wealthy, it would not come up that #4’s prom dress and #7’s braces will be taking priority over #8’s shoes and #10’s new dress for baby pictures. Because if BF is not independently wealthy, it will come up. Like it or not, legally in most states and pressure from the exes, always: the first kids in the lineup get priority. Your kids are going to come last.

    Then there’s the exhaustion factor: in my case, I wasn’t heartset on having my own children. I was the oldest of four and handled a lot of the caretaking duties with my siblings, then went right into caring for two stepchildren. It was fortunately okay with me that we didn’t go ahead and have more children. Because by that time I was utterly exhausted and simply could not contemplate starting a third round.

    I was able to reassure a friend who had the same thing happen. She’s in the eighth year of a wonderful relationship with a man who had two children with his ex. At first, there was no money for them to have children, and now… she no longer wants her own. When these two are out of the house, they are next going to enjoy the financial freedom and couple time they haven’t quite had yet.

    If you are happy to have your life take a shape you had never contemplated before and will ask of you things you don’t mind giving up, mazel tov! If your BF is incredibly stable, scrupulously fair, and pitches in on all household tasks, you just might make it through the next twenty years and have him to mostly to yourself.

    In my case, fate took a dark turn. Just as the youngest was becoming an adult, my husband abruptly died. We never did have “two of us” time. And he was only ten years older than I was.

    Think about this. Think a LOT.

  32. Speaking from my own experiences: I was almost always attracted to men older than myself, and never considered age differences a problem, though some people in my life were inclined to raise an eyebrow. My first three serious relationships were with men 20+ years older. They were wonderful, loving relationships and wonderful men and I wouldn’t give up those experiences for anything. A lot of who I am today — a lot of the good things — was nurtured by and grew out of what I shared with them.

    However, as I approached age 30, I realized that the one thing I had never been able to achieve with any of those men was a relationship of equals. That matters a lot to me, and I need it to be important to my partner, too; I need both of us to have equal respect for each other’s status, wisdom, and agency in the relationship. While I don’t think it’s impossible to find that even with a large age difference, I do think that makes it much, much harder to find. So I chose, from then on, to look for men whose ages were within maybe five years of my own (in either direction). For me, it was a good choice.

    My story is not yours, and only you can make your own choices. Just something to think about, see if it might — or might not — be relevant to your own situation.

    1. “I need both of us to have equal respect for each other’s status, wisdom, and agency in the relationship.”

      Thank you for putting so clearly one of my own feelings about relationships. That’s really good language to keep my priorities from sliding when/if I start dating again.

  33. LW, your own chosen signoff is a clue to your real feelings here. Are you asking for permission to doubt the seemingly good things about this relationship? You don’t need it—listen to your own voice.

    Was your family strict and severe? You mention things about your own background that make me wonder how much early-established expectations of male approval and control are contributing to this relationship’s seeming so wonderful. Step back (go a few days without seeing him and getting those strokes and praise from an older man who is “protective”) and look for patterns. Look for patterns in his previous relationships that you know of, look for ways in which you are falling into a pattern yourself. Make and keep room in your own life for yourself and your own development independent of him. Also, what the heck is he “protecting” you from?

    I get an echo of a grooming vibe from this relationship as you describe it. You got involved with him when you were 24, you don’t mention whether you’ve had a previous serious relationship like this one, and you do know that your own long-term plans are not settled. He has a ton of baggage and limitations: what if you decide to pursue career opportunities elsewhere, out of state, out of region? His seven kids and three exes limit his mobility, not to mention his finances and ability to contribute equally to maintaining yet another household/family. And if they aren’t limiting his finances, energy, and attention, there’s another red flag. (Unless he’s rich beyond my imagining and money is never going to be a problem.)

    Use two forms of birth control with this man, and make one of them something he does not have access to.

    1. “Use two forms of birth control with this man, and make one of them something he does not have access to.”

      Yes. Like, go get an IUD or an implant. Something he cannot touch, cannot hide, cannot fuck with in any way.

      1. An IUD could be messed with but, if my removal experience is anything to go by, you would notice. It has a… Feeling? Not pain but a feeling.

        1. I have an IUD, and … I feel like I would notice someone’s fingers messing around with my cervix.

        2. OMG WHAT. Someone tried to take out your IUD without you knowing? That’s beyond boundary-smashing.

          1. I hope Nashira means that the IUD was removed in the normal way by a doctor in an office, that she remembers the feeling, and that it would be noticeable if someone tried to remove it…? I hope?

          2. Yeah, WHAT? I really, really hope Nashira is confusing an IUD with something like a NuvaRing. If not, I’m super sorry, Nashira.

          3. …No, I had it removed by a doctor and replaced with an implant. I would not be copacetic about someone messing with my birth control.

          4. The cervix is partially dilated to insert or remove an IUD, so not something he could do on the sly. And hey, she doesn’t even need to mention it.

      2. ^^THIS. Reproductive coercion is a thing.

        LW, you say that he first said he was done having kids and is now saying that he might not be done. What were the circumstances around that change of sentiment? It might not be an issue if YOU brought up possibly wanting to have kids someday and, after some thought, he is considering changing his position. If, however, it was a random statement…that could be a red flag.

        I would definitely ask questions about his past experiences with birth control. If he talks about hating to use it, expresses anything along the lines of believing that a woman who currently doesn’t want to be pregnant should share the decision to use her own birth control, or talks about multiple bc failures/talks about highly effective bc means as if they are useless…watch out.

        Not all bc failures are accidental. And a man who decides that a shared child is the perfect hook to keep you in his life will pressure you to have kids and/or sabotage your bc.

  34. LW, I am your age exactly and I wouldn’t be uncomfortable dating someone who was 42; I have a couple of friends who are that age. But crucially, they treat me like an adult who is their equal, not like a child. Your point about ageplay worries me a little here – outside of the teasing, does he take you seriously? Or does he use your age as a way to shut you up? Does he value your opinion on grown-up topics (whatever he might perceive those to be – politics or finances, for instance)? Does he respect and value your work, encourage you to believe in yourself, and seek promotion if appropriate? If you were having a conversation about a neutral topic, would there be a significant difference in the amount that he listens to you and asks you questions than if he were having the same conversation with a male friend of the same age as him?

    In relationships with big age gaps, there can be the danger that the older partner doesn’t take the younger one seriously – even if they have the best of intentions. If these conversations are harmless, teasing fun with a sexy edge, that sounds great and you shouldn’t feel weird for liking it. But if you start to feel like he doesn’t respect you as his equal, that turns this into a massive red flag.

  35. My husband is 15 years older. We met when I was 30 and he was 45. But he had never been married (which my parents and some friends thought was a red flag) and had no children. We’re a great match, though, and while I’m a bit freaked that he turns 60 this year, it’s worked out very well. We have no children, because neither of us wanted them.
    So honestly, the age difference in your case is not what gives me pause, but the fact that he has so many kids with several women does. What does that say about his ability to focus and connect? Those kids all deserve a full-time dad, but how is that possible? And if you two do have kids, he’ll be stretched even thinner. That is if he sticks around. He doesn’t have a good track record.

    1. Same. My parents have a 12 years split (mom was 30, dad was 42). He did have a previous marriage with three kids, but only them. (Fortunately, we are starting to be able to form relationships with my half-brothers and -sister, and their children – they are overseas.)

      It really is the 3 mothers and 7 kids that is the concern.

    2. My dad is 11 years older than my mom is. He was married before Mom, with two kids from that marriage. I’m told that my maternal grandparents (especially my grandfather) were NOT pleased at first, and I can see their point of view. But they came around after they got to know Dad, because Dad happens to be a pretty awesome person and a good father and husband. He and Mom are still happily married, 40+ years in, and being awesome grandparents to my younger sib’s kids.

      My husband of more than 15 years is 13 years older than I am. It’s never made much of a difference to us. But when we met, I was 26, had graduated from college, was working and living independently of my parents, and had been doing so for several years. He was widowed, no kids, and no desire for kids – which suited me just fine. We have a lot in common, but with enough distinctions in our areas of interest to keep things, well, interesting. He has never once failed to treat me as his equal and partner, and he will readily say out loud to other people that I know more about some things than he does, because it’s not an ego thing for him. He doesn’t act threatened if I’m better at something than he is. I’ll just as readily defer to him or seek his input and help when it’s his area of expertise. We make a good team.

      I think, OP, that I’d suggest that you ask yourself some things. Good questions would include: Does your BF treat you as a functional adult? If you happen to know more about something or be better at something, is that ok with him, or does he seem to see it as a threat?

      What about when you disagree? Does he talk it through with you in a respectful fashion, or does he go all “don’t worry your pretty little head about it,” or “I’m older so, clearly, I know better than you do and I don’t have to listen to you”?

      Does he care about what you want – is he supportive of your ambitions?

      Honestly, the 7 kids with a number of different women does disturb me a bit. But you are the boss of you. What I would suggest is, as other posters have said, take a careful look at how he is with his kids and with their mothers. Do they get along? Is he respectful to his exes? Does he run the exes down to or in front of the kids?

      I would suggest taking it slowly and being diligent about your birth control – and while I hate to sound paranoid, I’d strongly suggest that you be diligent about making sure he does not have access to said birth control. And if you do decide to take things slowly, how does he react to that? If he pressures you to move faster than you want to, particularly with any hint of “you’re too young to know what you want and you should listen to me” – RUN. RUN LIKE THE WIND.

  36. Have you ever seen the movie Guinevere, starring Sarah Polley? There is a scene that set my standard for how to decided if a relationship with a big age difference is creepy. In the film a very young woman gets involved with a charismatic, much older artist and moves in with him without telling her family. Her mother eventually tracks her down and shows up at the loft unannounced. The mother says:

    “What is a man of your age doing with my daughter? It’d be easy enough to say you’re afraid of mature women, but that’s so glib. Afraid of what, exactly? So I kept thinking. And then it hit me. I know exactly what she has that I haven’t got. Awe. That’s it, isn’t it? I mean, no real woman — no woman of experience would ever stand in front of you with awe in her eyes…”


    I suggest you just check in with yourself about this. Captain’s advice about how he interacts with women his own age is vital. The way you describe your interactions with his kids concerns me (not anything you did!). Stopping by for a couple hours of games and snacks is fine but I noticed you didn’t mention whether they are also there for extended periods of time.

    1. whew. that exact thing was what kept me in my marriage so long. awe. we were the same age, but his accomplishments were literally awe-inspiring, and that became the basis for the entire dynamic of our relationship. since then, i try to seek out people i admire, but if i’m in awe of them, there will always be a power imbalance.

    2. The actress that portrayed her mother is Jean Smart. YASS QUEEN. That movie was awesome, and she was the best thing in it.

    3. Yep, my current relationship sounds a lot like the one described by Firecat above. He’s 13 years older; we’ve been together 10 years but barely notice the age gap day-to-day because we have equal status in the relationship. He has 3kids – now delightful young adults – from his only previous marriage, and treats their mother with respect. He loves the kids he has, but doesn’t want any more – which works out well, as I never wanted any.

      Boy, what a contrast with my previous long-term boyfriend! Similar age gap, but he had 3 kids from 2 previous marriages and would talk about wanting more with me even as he ran their mothers down. And didn’t introduce me to his family for the first five years – told me his parents hated the vey idea of me and wouldn’t accept a new girlfriend, although subsequent events led me to doubt whether he’d even informed them of my existence. Red flags a gogo!

      As for the awe thing: I am in awe of some of the things my current partner has achieved. On the other hand, I’ve also wiped his arse when he’s been incapacitated by PTSD plus alcohol (self-medicating up the yang-yang). So, huge respect, but no illusions left.

  37. LW, the Captain is right that nothing you’ve said about your partner or the relationship means it CAN’T be happy, successful and good for you. An age gap doesn’t necessarily mean a bad relationship, like some commenters here can demonstrate. Lots of people have talked about things to look out for in terms of your partner’s relationships with other women, his exes and his kids, which are important.

    I have been in a similar situation and what eventually ended the relationship was the fact that 1) we were at different stages of our lives and wanted different things and 2) I felt like I could never be truly an adult and an equal. My ex was 20 years older than me (I was 21 when we started dating) and we had five pretty good years together. I feel like the relationship enriched my life in many ways and we had some great times I would never wish away. But it ended – and that was ok too. For us one problem was that my ex had been divorced and didn’t want to marry again, and definitely didn’t want kids. These were questions I hadn’t yet settled, or things I didn’t feel the same about. So just as an example, If you don’t know if you want kids, and it turns out your partner is done having kids, you might find you want different things in the future.

    In terms of telling your parents, they may well be horrified. Mine were absolutely. But what mellowed them was seeing over time (probably about a year) that my ex was good to me and good for me. Your parents may hate the *idea* of your partner, but over time could they learn to love *him*?

    I also find, like the Cap and others here, that the older I get (31 now) the more side-eye I give to my ex, and to older men who date 20-something women in general. If it’s a pattern, it’s not a good one.

  38. LW, the Captain is right that nothing you’ve said about your partner or the relationship means it CAN’T be happy, successful and good for you. An age gap doesn’t necessarily mean a bad relationship, like some commenters here can demonstrate. Lots of people have talked about things to look out for in terms of your partner’s relationships with other women, his exes and his kids, which are important.

    I have been in a similar situation and what eventually ended the relationship was the fact that 1) we were at different stages of our lives and wanted different things and 2) I felt like I could never be truly an adult and an equal. My ex was 20 years older than me (I was 21 when we started dating) and we had five pretty good years together. I feel like the relationship enriched my life in many ways and we had some great times I would never wish away. But it ended – and that was ok too. For us one problem was that my ex had been divorced and didn’t want to marry again, and definitely didn’t want kids. These were questions I hadn’t yet settled, or things I didn’t feel the same about. So just as an example, If you don’t know if you want kids, and it turns out your partner is done having kids, you might find you want different things in the future.

    In terms of telling your parents, they may well be horrified. Mine were absolutely. But what mellowed them was seeing over time (probably about a year) that my ex was good to me and good for me. Your parents may hate the *idea* of your partner, but over time could they learn to love *him*?

    I also find, like the Cap and others here, that the older I get (31 now) the more side-eye I give to my ex, and to older men who date 20-something women in general. If it’s a pattern, it’s not a good one.

  39. To me the worrisome part is the number of ex-wives. That’s what I, personally, would take a hard look at. That said, one of the great love matches that I have seen in my own life was with a difference of fifteen years, and was not the first marriage for the gentleman in question. So, as other people say, go slow. Take a hard look at what’s up and what you really see as happening. Then go be happy, either alone or with him. Whatever works for you.

    1. Yes, that would be my concern as well. My partner is 21 years older than me, but I was older than the LW when we met, he’d only been married once before, and we were on the same page as far as children were concerned. He had three from his previous marriage and had a vasectomy, I didn’t want any so that was fine by me.
      One divorce – the marriage could have been a youthful mistake.
      Two divorces – getting a bit riskier, but the second marriage could have been a rebound mistake.
      Three or more divorces – this person is a high risk choice. The more divorces in his/her past, the more chance that this person just isn’t very good at relationships.

      1. True enough. But still, three relationships that resulted in children is pretty much equivalent to three previous marriages.

    1. I suspect comments by someone who has been silent lately are moderated. Mine often appear after several hours, but if I come back soon and comment further, the delay is not there.

  40. Hi, LW.

    Something that I don’t think anyone has talked about is that this relationship is with a co-worker, and that it’s semi-secret, and your co-workers are not necessarily uniformly happy for you. Though there may not be anything in your company handbook against having a relationship with a colleague, if your BF is in your management chain that’s a big concern. What would happen if everyone at work finds out about this relationship? Ask yourself if you’ll be happy in this relationship just as it is in two years, five, ten. If you’re not sure, then take it slowly and enjoy what you have for now.

    I don’t want to be all doom and gloom, though. My mother met and married my father when she was in her early 30s, and he was 20 years older. They were devotedly married until his death. He had an ex and two kids when they met, and while it wasn’t always easy that my mom was just a bit older than her step-daughters, it worked out.

    Best of luck!

  41. LW, I hope that my suspicions are wrong, but could you find out (preferably from your SO’s ex-wives) whether all seven children were planned for?
    If they were “accidents”? BIG red flag. Either he doesn’t care about birth control or, as is too often the case with controlling (protective?) men, he’s deliberately messed with birth control in an effort to keep his exes in a relationship with him.
    Keep your eyes peeled, LW, and good luck 🙂

    1. Oh shit this.

      Accidents happen. Accidents that happen over and over again? Are a sign of either negligence or hidden intent. It might not even be about “keeping exes in a relationship”. I briefly worked with a rather awful man who had an *unknown* number of children with a whole bunch of women, mostly significantly younger than him. He wasn’t interested in supporting them or helping raise the kids or even paying child support. He just felt *manly* when he was “sowing his seed”.

      I’ve also known guys who told new partners they had X children by previous partners… and then a couple of years down the line it turned out they had several more. Who they didn’t support or have relationships with.

    2. This. I mean, I’m one of 7 kids. And with that many kids, they are 1. on purpose (for both parents) 2. accidental (for both parents) 3. accidentally-on-purpose (one parent deliberately messed with the birth control).

      Category 1 is not really a problem.

      Category 2 indicates that somewhere along the way dude has failed to learn how to use birth control properly and responsibly.

      Category 3 means that either he, or his exes, are bad news people with bad news behaviors that will bad news fuck up your life if you get too involved.

  42. 1) You can’t tell your parents…that might be a signal that you have qualms about this relationship that you haven’t fully explored or admitted to yourself…or it might be a signal that you have qualms about your family and are afraid to be your real self around them…or some combination of both. You definitely need to spend time sorting that out. Because if it’s a family problem, you’ll be dealing with this with any future intimate relationships, or else this one will last and you will actually need to let your family in or go the other direction.

    2) I knew one guy who had 5 kids (from one mother). They were divorced, and he didn’t have custody. But he loved his kids and made them a definite priority in his life. If these kids are important to your boyfriend, then they should be a priority in his life, and their needs should factor into many of his decisions, and that will affect you. And as others have pointed out, at some point that does entail certain responsibilities on your part too, if only to figure out how to balance all those competing needs.

    3) Definitely think about what having kids with this particular man would entail in terms of money, time, attention, logistics, etc. Is that something you could envision and live with, embrace even? The Sheelzebub Principle should definitely be adapted to think about this scenario–what would co-parenting with him be like? What would being a single mother, 4th in line in this instance, be like? Definitely have all the talks, in detail, to explore this before even considering the absence of contraception.

    4) Age play–sounds like you’ve discovered some kink in yourself and it’s weirding you out. Definitely explore that as you can on your own, with your boyfriend, in therapy, whatever. In terms of age difference–others have pointed out the gendered dynamics of this, particularly in terms of unequal power and the fact that so many times middle-aged men are intentionally exploiting the lack of wisdom/experience/self-knowledge/self-confidence of twenty-something women. The age play you’re describing is definitely stepping on that turf in terms of power dynamics. Large age differences aren’t inherently problematic and don’t always lead to bad outcomes, but the risk is definitely there and the probabilities slant in that direction.

    I knew one couple with a large age gap–she was a teenager and lied about her age when they met. They were married for many years and seemed to be happy together, until the day she decided it was over and divorced him because she’d spent her whole adult life married and wanted a chance to explore, He was left pretty devastated. So not exploitative, but she ultimately regretted her bypassed youthful exploits. So that can happen instead of the older man dumping the woman for a still younger model.

    I have usually been attracted to older men, and the largest difference was 14 years. I didn’t twig to this at first until he started talking about the Viet Nam war. I was 25 at the time. it turns out he was lying, married, cheating, etc. Then there was the time he got drunk, fell asleep and then woke up and flashed back to his soldier days while we were camping in the off season. It was before the days of cell phones, and I was able to get away and use a pay phone to call a friend to leave a description of me, him, the vehicle, and our location in case I went missing so there was some starting point for the investigation. I did some foolish things in my youth, I tell you. Didn’t break up with him despite being afraid for my life. But that’s a bit of an extreme example. The truth is, I just didn’t have enough experience with relationships and just living in the world, or the language and tools to recognize how fucked-up it was, how to say no, how to take care of myself, how to expect more. Still working on it 20 years later.

    It sounds like you’re asking the right questions and thinking about the big picture. Keep doing that. Have all the difficult conversations at the front-end. It makes it easier to figure out it’s not a good long-term fit for you, or confirm that indeed you are making the right choice for you. Easier to disengage *before* living together, owning property together, getting married, having children together, in any or all combinations. Once you’ve been through all the difficult conversations, explored all the details, gotten into the nitty-gritty, your relationship will either be stronger or you will move on with less self-doubt either way.

  43. Dear LW,

    Sheelzebub comes to mind.

    How do you imagine this relationship in a year? Or 5?

    What will a semi-secret relationship feel like then?

    So, if it becomes a relationship that everyone knows about, how do you get there?

    LW, I can imagine many things going right and wrong (mostly wrong) but I am not you. If I were 25 and in love with a man in his 40s, and he had 7 children from 3 previous relationships I would be terrified.

    I would imagine a life in which none of my dreams were our priority because he’d have to put 7 people before me. And if he didn’t put them before me I would lose respect and liking for him.

    So I second the Captain. This can be a wonderful and important relationship even if it doesn’t turn out to be marriage and kids together. Or maybe, this is a relationship to back away from.

  44. Pretty much echoing all of the advice here. Take your time, go slow, ask lots of questions, and listen to the answers you get to those questions. Or the non-answers. Sometimes what a person DOESN’T say in their answer can be just as telling as the answer itself.

    My cousin was 23 when she started dating the father of her son. He was 42, and had kids that were only a couple years younger than him. He ended up being an alcoholic jerkface with verbally abusive tendencies who refused to work, but my cousin was starstruck by him and didn’t see the signs of future problems until after she had already moved in with him and gotten pregnant by him. She has repeatedly said that her one regret about all of that was that she rushed into things too fast (she went from “I met this guy” to “we’re living together and I’m pregnant” in about 3 months), and that if she had taken the time to actually date him and get to know him first she probably would have seen all of his bad habits ahead of time and wouldn’t be where she is now.

    You are young. Taking your time with this hurts nobody. Not all men who date younger women are scumbags, but scumbags often target young women because it is easier to manipulate them. Above all else, look out for yourself, and everything will turn out okay. That ‘okay’ may or may not include this boyfriend, but your happiness is more important than who you are or are not dating.

  45. LW, if you’re happy right now then there’s no need to break up! You can just enjoy the relationship now and decide to break up later if you want- no harm, no foul. Or, if in a few years after you’ve taken a good hard look at those red flags and addressed them you decide to move forward and become more serious with him then that’s great too! As the rest of the commentators have said, however, you should probably go slowly and address those issues first. Best of luck!

  46. On top of the other questionable signs mentioned that whole “might not be done yet” thing with children is concerning. It’s not that he might want more children, it’s the phrasing – “might not be done yet” is a bit unilateral. Does he expect you to have his kids if he chooses that he does want them? Have you even been asked about the issue?

    Then there’s the degree of secrecy. Keeping it from parents I get, but coworkers? They aren’t cherished family, essentially none of them have the levels of control family do, the whole matter of crushing beloved parents and being made a pariah are not issues. So, why is that being kept secret? I’m not saying that you don’t have a good reason, but I am saying that you should know what that reason is.

    I don’t know the particulars of your situation, but my first instinct here is to bail.

    1. I think she said the coworkers do know? Because she said some originally reacted negatively but then got used to it.

      I read it as she’s the one who doesn’t want her family to know.

      1. It sounds like most of their coworkers don’t know — “a select few people at work” know, but not everybody.

        That said, a lot of people think that’s the most professional way to handle having a relationship at work — that anyone who only sees you at work should not be able to tell from your behavior that you and your partner are anything more than coworkers who get along well. It’s not the route I personally would choose, but depending on your workplace and your idea of professional behavior, it’s not unreasonable for most of their coworkers not to know they’re dating.

      2. She said “a select few people at work” know, so it’s some coworkers, not all. And I do wonder at the reasoning behind that.

        1. Well, LW mentions they work together– it could have begun out of a desire to keep things from being awkward at work, and then become more difficult to bring up. Not, perhaps, the most mature way to handle things, but a trap I can totally imagine setting for myself in LW’s position.

    2. The “I might not be done yet” part jumped out at me too. I found it threatening, in the sense that it was said as a joke (“Here’s what I’m going to do, but I want to have plausible deniability in case you try to hold me responsible for my actions”) instead of discussed with the LW in a serious way.
      LW, this may be his way of telling you that he intends to have children with you (with a subtext of “I care more about my opinion on this than yours”). Would you like to have children at this point in your life, with this man as their dad? Listen to your gut and see how he takes care of his seven children (he won’t love yours better), that’s important data.

      1. I actually read that as ‘if having kids is important to you, I might come around to the idea’.

      2. I actually took “I might not be done yet” differently: I thought he was trying to reassure the LW that he might be willing to have more children with the LW even though he already has 7. So, not as a threat or a demand, but as a tentative offer.

        1. I read it that way, too. That if it was important to her he might be able to get into the idea.

        2. I saw it this way, too, not that it’s necessarily a *good* read on it either! Because I read it as a kind of desperation-please-don’t-leave-me-for-a-real-functional-family move on his part, a way to keep her sunk in longer. And if that’s the case, LW should take a long hard look at his parenting all the more, because someone who doesn’t really want kids– but is willing to father them in order to appease a partner he fears will realize that, on balance, the cons of this arrangement outweigh the pros– is someone who is not going to be a good parent or partner once those kids materialize.

        3. “I might not be done yet” is kind of bad news either way. Either he’s just saying it to make her stay, in which case it’s a string-along move, or he’s perfectly willing to have yet more kids who aren’t going to live with him or be “his responsibility” in any 24/7 kind of way.

    3. Yeah, that lack of certainty and the wink-wink aspect of it hit me the wrong way, too. So he says he doesn’t want more children but he *also* says he might not be done yet? If you’re having the “are children in my future if I stay with you” discussion and he’s coming out with that sort of hand-wavy nonsense, you might want to think twice. An adult having a conversation about child-having plans with their partner should be speaking more frankly than that.

  47. LW, you can do what you want, but imo if you want to have children, go elsewhere. He does not have a pattern of stable relationships, for one. The other reason is that research has been coming out that suggests older fathers (40+) may be passing on more health problems to their children due to sperm mutation and defragmentation. It looks like men have a biological clock too, and if you want to have kids the ages of both parents are equally important.

    1. My earlier response got eaten by the spam trap, so here’s a shorter version: Obviously health and age of parents and their availability will matter for planning future progeny, but please stop using “disabled children”/”children with health problems” as a boogeyman. Children with health problems are people, not cautionary tales.

      1. Children with significant health problems who are 8th in line (and 6th in the still-being-supported group) who may need a lot of extra attention and money are a consideration, though. Because at that point, you do have to make some big decisions as to who gets your (most likely very limited) time and money which will be unfair to either the child who has to have to have the money or time or the children who are asked to sacrifice for their sibling.
        That being said, if he didn’t already have a large brood, I don’t think it needs to be a serious consideration.

        1. Look, I always think that it’s a good idea to take a look at your finances and the stability of your situation, including the age and health of the parents, when you’re looking at having children. And taking into account how many kids you already have and the possibility of needing to care for a child with disabilities, which does take more resources, is an important part of that.

          But the way it’s phrased is so often, “Be careful if you have kids when you’re older, you might have a DISABLED BABY.” Which sounds just as gross as if you say “You might have a GAY BABY” or “You might have an AUTISTIC BABY” or “You might have a FAT BABY.” Having a kid who has to deal with being disabled and/or fat/autistic and/or otherwise non-neurotypical/gay or otherwise queer is more of a parenting challenge than having a kid who is skinny, able-bodied, neurotypical, and straight, and might cost more money, but talking about them like they’re negative outcomes is one more way our language marginalizes people, especially kids, for not fitting into proper boxes. Disabled kids are people. Gay kids are people. Fat kids are people. Don’t use “This guy might have a higher probability of non-perfect children!” as an excuse when the real problem is “This guy might not have the energy, time, money, and attention to care for another child, especially if that kid has any extra needs and doesn’t raise themself.”

        2. Comment eaten by the spam trap again, so the short version: I think it’s very, very important to separate “Doesn’t have the time and attention to care for a kid who might need extra money, time, attention” from “YOU MIGHT HAVE A DISABLED BABY.” One is an important consideration when you’re planning for your future. One is fear-mongering that turns real human beings who have feelings and lives into a thing that potential parents should be afraid of.

          1. Yes, in part because the only way to guarantee that you won’t have a disabled child is to not have children at all. (There are no genetics or prenatal choices that will protect a child from car crashes, for example.)

        3. Eh, this is a red herring either way, IMO. If LW and her BF were perfectly made for each other and going to be together forever, “slightly increased risk of health problems” isn’t a reason to completely throw that away. But if it turns out that he is not a good partner, then the possible health problems thing is a complete non-issue. She doesn’t need to marshal every little tick against him.

  48. “It took a while for me to put aside my prejudice”

    You are still a good and lovely person if this is too much for you. It’s not “succumbing to your prejudice” or failing to overcome your “prejudice” if you decide that this situation is not for you. You don’t have to be chill and cool about this to be a good person.

    1. Exactly. Not being a bigot doesn’t mean you don’t get to have standards and boundaries.

      1. This stuck out to me as well. I have been in several relationships where I found myself doing the whole “well I shouldn’t discriminate against him for Thing and it nearly always turned out that Thing was either a huge red flag or a major problem in itself.

        I guess the general takeaway is probably something about women being taught to discount our intuition/gut sense/self preservation to preserve the feelings of men. This theme is so pervasive and gross and I wish I could expunge it from our culture.

        1. Oh yes. I wish so hard that I could go back and tell my younger self that my romantic feelings do not in fact have to be “fair.”

          1. Yupp. Relationships do not fall under reasonable doubt rules a court has to take into account or non-discrimination rules an employer has to comply with. You should obviously not treat another person badly, but the deciding factor in “is this relationship happening” is: Do you want to be in this relationship? Going “but it’s unfair towards him” or “he has good sides too” is pretty close to making pro and con lists and in my opinion, if you are at the pro and con list stage, your gut has already told you it’s over but your brain is still dragging its heels.

          2. Replying to winter below (out of nesting):

            ” if you are at the pro and con list stage, your gut has already told you it’s over but your brain is still dragging its heels.”
            THIS THIS THIS.

      2. And it’s not “bigoted” or “prejudiced” to notice that someone has seven children and four ex-wives and wonder how all of that happened. This guy is in the place he’s in now because he made a series of choices that led him here. Now, I don’t *know* how all of that went down, but I’m going to speculate that there were some accidents in there, and perhaps also some times where he was more optimistic than realistic about how a particular marriage was going to play out with children in the mix. Simply put, it seems likely that at some point the dude made mistakes. And it’s not bigoted or wrong or unfair to notice past behavior and keep it in mind while you’re evaluating how you can expect a person to behave in the future, and with you. That’s called being smart.

        LW, I really hope that this guy isn’t trying to act like you’re wrong, “prejudiced,” out of line, or otherwise behaving badly if you admit to him that his history worries you or gives you pause. A good partner will respect your judgement about things like this. If he wants to explain his earlier behaviour, that’s fine; but if that explanation starts to sound like he’s telling you why you shouldn’t take his earlier behaviour into consideration when you’re deciding what kind of relationship you want to have with him, that is not okay and you need to get out of there, because either he’s lying to himself about his pattern of behaviour, or he’s lying to you, and neither of those is okay.

    2. It’s good to be open-minded and question your preconceptions. But I have, a couple of times, become so open-minded that my brain fell out.

      I wouldn’t recommend it.

      You’re a thoughtful, compassionate person, from what I have read. There is nothing wrong with being a thoughtful, compassionate, caring person who also knows what she wants, whether that is or isn’t him.

  49. LW, is this relationship “at work” with your -boss-? Because that’d help explain why the colleagues felt that obvious revulsion.. Still, while I’ve ended up with colleagues a lot myself, and happily on the whole, all I can say is that when you stray that way it’s good to keep the resume in tip-top shape. The other commenters seem to have the rest of the potential ickiness quite well covered :-(. I’ll just second the thought that I’d be leery of someone that age who doesn’t seem able to have stable relationships, and worse still blames his parents for it.

    1. I am glad you focussed on this –I have to say, IF (not saying that it is true) that is in fact the case (boyfriend has direct or indirect authority over LW), it would firmly tip me over into the BF is a “predator” categorization and I wouldn’t be necessarily be particularly impressed with the LW’s conduct either. it also puts the employer at risk (one of the reasons workplaces have disclosure requirements regarding relationships). Imagine a similar situation with the girlfriend eventually getting a no doubt “well deserved” promotion over someone who wasn’t sleeping with the boss/boss indirect. Imagine the hostile work environment established when your worth as a woman is determined by your fuckability. I understand the “no one can life your life but you” mantra and pleas for judgement free zones but acts and omissions also have consequences or others and those impacts will (and should, on at least some occasions) lead to scrutiny.

      It could, however, simply be that the workplace revulsion comes from age difference and/or knowledge of his personal circumstances. There may be unfair societal assumptions at play or, alternatively, the smoke may not be coming from dry ice. No doubt that’s where the particular factors of the relationship will help establish which scenario is true.

  50. your co-workers may have seen this guy in this relationship with someone else before. Actually, I’ve seen this guy in this relationship before. Manager, married, 5 kids. Affair with much younger woman at the office. Co-worker got pregnant, manager lost his job, co-worker lost hers, he left his wife. Now has 7 kids and just left co-worker for another much younger woman (I heard from another co-worker who kept contact)

    Make sure your birth control is safe and not able to be tampered with

  51. Sometimes, we tend to see the red flags in a relationship but then we equally always tend to brush them aside. I think there are a lot of red flags here. I also think that the letter writer is seeing/sensing these red flags already.
    Personally I feel like she should take some time off this relationship and really think about what she wants in life. I’m kind of seeing a pattern in this man’s relationship with women and this woman also needs to see it. So she has to really ask herself some hard questions first because getting children with someone is a sealed deal.

  52. LW, having doubts and asking questions is not always a red flag in relationships. It’s normal and even healthy.


    These questions you’re asking? You’re asking them for a reason. These doubts? You’re having them for a reason. The sneaking suspicion that your family would not approve, so much so that you haven’t bothered to tell them for a *year*?

    Look closely at these doubts and questions and justification for secrecy. I think in this case, and with these questions and doubts, and this many of them…I think the answer to the questions lies in the fact that you’re asking them in the first place.

    No matter how lovely he is, you’re having to talk yourself into not running for the hills. No matter how compatible, you seem to be trying to quiet this tiny inner voice that’s going, “I’m not okay with this.” It feels unfair, it feels like you’re judging decisions that you have no business judging, it feels like you’re faulting him for things he cannot help.

    I think the reason these questions keep surfacing is because you know the answer and you keep hoping you’re going to get a different one.

  53. I want to weigh in on his children. I’m a stepmother, and when I married my husband I didn’t truly understand the implications of that. We had things planned out, it was all going to be great–until those kids unexpectedly came to live with us much earlier than we had planned. And we couldn’t afford them (their mom used a loophole to get out of paying child support). And my husband’s work hours meant I was raising them alone. Also, like you, I wanted kids of my own. I only have one child, though, because the cost of supporting more than 3 children was too great for us. At least, if I wanted to have any semblance of quality of life for myself, too.

    I can’t imagine how much it must be costing to support 7 children. Is he rich? Then maybe it’s all okay, but circumstances can and do change. Is he skimping out on child support? If that’s the case, then under NO CIRCUMSTANCES should you consider having children with him! Also, while the mother of 5 may be doing most of the heavy lifting in terms of child care, what if she gets hit by a bus? Those children will come live with your boyfriend. Are you willing to live with them and help raise them and support them (because mom won’t be contributing anything financially in that case)? If you are considering a permanent future with him then you have to be prepared for that possibility, because it does sometimes happen.

    What is your boyfriend like with his kids? Is he actively involved in their lives? Is he willing to discipline them and set boundaries or is he just the fun weekend guy? My husband told me the kids weren’t my responsibility too, but then he worked 18 hours a day. So…um…who exactly was supposed to be making their dinner, supervising their homework and chores and baths, going to parent-teacher meetings, reading them bedtime stories, taking them to the doctor? It was all me. If you want a permanent future with this guy, PLEASE discuss these things in advance, ideally with guidance from a counselor trained in working with stepfamilies.

    Until you are at the point of wanting to make a permanent commitment with him (either marriage or kids), however, enjoy the heck out of your time together, and don’t feel guilty or weird about two adults having a consensual relationship (or about whatever turns you on). But as others have said…please use birth control religiously until children are a conscious and well-planned decision! I wasn’t that smart, and while I adore my son, if I could go back and do things differently, I would in a heartbeat.

  54. What’s the chain of command like at work? Where are you, relative to each other? How big is the workplace?

    At my last workplace, you had to go up about five layers of management before my chain of command met the chain of command of the person I had an office crush on, and while he’s a team leader (senior member of the team under the same manager) and I was an assistant (taking orders from a bunch of people under my same manager), we were on the same relative rung of the hierarchy in our separate departments. Though he’s fulltime and I was a contractor, which was a small point of inequality in an otherwise pretty level friendship. The fraternization policy is pretty much “as long as nobody’s getting hurt”, though I’m assuming that nobody should be dating their direct report.

    If there’s a power imbalance at work, that’s something else to watch out for.

  55. (Liberal amounts of projecting below, take with appropriate dosage of salt.)

    I generally have no problem with age-disparate relationships – I lean towards them myself, probably due at least in part to being the product of one.

    However, the main point of yours I’d comment on is #3. As stated, my parents were pretty far apart in age, and he had three kids in their teens/early twenties by the time I came along. My mom wanted a big family. He wanted to be done. I was the compromise.

    And honestly, that’s a sucky kind of feeling; I always felt like I had to compensate both for my mom’s sake (being the only kid she ‘got’ to have) and my dad’s (not being too much trouble because he didn’t really want another one anyway).

    I’m guessing when your guy said he didn’t want more kids, that was the truth, and his recent hints are him realizing he could lose you if he didn’t give you that option. If you decide *you* want children, I’d have some really serious discussions with him about whether that’s something he genuinely wants, or if he’d be putting up with it to make you happy.

  56. I know a woman who married a much older man at 18, a man who took care of her (and their kids) financially and loved her deeply as much as she loved him. Five kids later and one only a few months old, he passed away. While he’d been able to ensure that his family wouldn’t be on the streets in the event of his death, she had some hard decisions and many difficult years to go through the balancing act of working along with college – she’s sacrificed a great deal to take care of her kids, only now that she’s 60+ has she dated again (this time the guy’s younger but only by 5 years). Life can change course in a moment, even in the best of relationships things don’t have to go bad for it to just…end…

    To sum up…you don’t have to decide on forever quite yet, pay attention to how he parents and how he treats/speaks to or about women his age, but you still don’t want to get into a holding pattern for well….almost forever. We don’t know how long we get in life.

  57. The Captain touched on this, but what further would people who’ve been there suggest for the “what bad patterns are/aren’t likely to recur in a fourth marriage (or similar weight relationship) from the previous three?” I honestly have no idea what I’d do, but I’d want to know.

    In a job interview I’d just ask, but this isn’t a job interview. (We might be happier if it were more like?) Previous marriages will come up in conversation — or somehow they don’t — and that tells me something, but I think I’d want more than I could get without bludgeoning.

    Well, it’s basically the same as any new relationship where you’re wondering about their track record as forecasting future behavior. Where I know how to open more neutral topics like “so what’s your history with poly?” but have never really ‘interviewed’ for negative traits beyond knowing their ex. And sometimes looking back I’ve wished I’d done more. So I’d love tips.

  58. Putting aside Dreamboat Snr and all the obstacles he brings.. what do you want from your life? I would have been on the fence about kids when I was 25, so I can relate to that.

    25 felt young enough not to have a clear wishlist plan for my future. It was young enough to only just be independent from my parents, despite my concerted efforts in my late teens. Nothing in my own life was ideal or my first choice, I was low on funds and many of my choices were pragmatic ones you make when you are twenty something and not in a position to choose what you want vs what you can afford.

    It was hard to dream about what I wanted to be in my forties among the hand-me -down furniture and crappy temp job of my twenties.

    I am 32 this year. I reached a point where my life was a result of the drifting fate of previous years where I went with the flow. People showed up and I grafted on making those relationships WORK dammit and if my life got neglected well, wasn’t that all part of saving others and being a noble woman who redeems lost boy men with hot bodies and a multitude of issues and wasn’t I supposed to be a dutiful daughter and fix drama?

    One New Years Eve I wrote a wishlist that seemed impossible at the time; a beautiful home, a fulfilling job in my field, somewhere to write – because that’s my passion – and a dog. Maybe a man too but only a top notch drama free man. I have those things now, which honestly, I am still amazed by.

    I had a wishlist. I stopped putting time and energy into things that took me away from my wishlist. When things appeared that were shiny but not really workable, I went back to my wishlist and considered what I was prepared to gamble. Sad eyed- lost – boy – ‘fix me’ fellas came along with hot bodies and told me only I could help them. I resisted. One day a woman at a networking event brought up this great new project; the one I now work at. One day I emailed a guy I liked the sound of on a dating site and three years later, I have a writing desk that he created in the home we share and hugs from his dog.

    It is easy to let life become a whirl of drama and others people’s needs. My advice is to think about your wishlist or even write one and start to give yourself the consideration and faith that you give him. That doesn’t have to mean a break up. It doesn’t mean your list needs to have an astronaut on it. You don’t need to do an Eat Pray Love sort of voyage. But give yourself a pause to ask yourself what you want.

    At 25, so much happiness and joy awaits you if you know how you will recognise it. Don’t shortchange yourself the chance to dream because you’re x boxing with Dreamboat Snr’s kids. Any man worth his salt will want you to have your wishlist and actively support your independent efforts to reach it.

    You don’t have to choose between the life you want and the life a man has going on. It’s not an either or thing. A good partner adds to your life more than they limit it.

  59. Minus the children could be my story. Took the go slow option and that was his excuse for the first time I was cheated on. The second time was with a colleague, even younger than me. (And both ~10-20 years younger than him). Which may not happen for you, but I will warn it’s made a job I love really quite horrid at times. As there’s a huge power imbalance. I’d quit, but I genuinely adore the job 98% of the time. The 2% is vile, though.
    Anyway, in your case I’d look for patterns, and also consider whether you’d be willing to/easily find a new job if it ends badly.

  60. There are seven children with a claim on his time and other resources, and the children’s mothers (if there are offspring, there’s no such thing as an ex) and there is a cold equation there, too: either he is a committed and involved father, or there’s something wrong.

    If he’s not interested in being a father, why did he have seven children?

    And it’s really not possible to be indifferent to the children if they are around. The rules for these relationships are best handled with not meeting the children until you are a part of their parent’s life. And if you are, you are unavoidably a part of theirs too.

    1. Yeah, that’s the dilemma. Either you’re dating a parent very occupied in raising minimum 5 kids (for the sake of argument I’ll say the older two are grown), or you’re dating someone who really doesn’t fully involve himself in his own children’s lives.

      Either can be something you’re willing to deal with, but each comes with fairly major sacrifices.

      In the first case, it means accepting that the kids WILL change your life, a lot, and take up the biggest chunk of his time and energy outside work. Which may be fine and even lovely, but it’s something that will have a huge effect on your life.

      In the second case, even if you find you can still respect that person (maybe there are circumstances that make it make sense to you) would you want that for your own children? People do sometimes parent their different children differently, custody laws can back people into corners etc, but on the whole, the best predictor of what kind of parent someone will be in the future is what kind of parent they currently are.

  61. Hi LW. +1000 to the Captain’s first para (and indeed the rest of the answer). You say he’s wonderful and gentle and kind etc. – OK. For some reason I’m getting a Miss Marple I knew a case just like this in St. Mary Mead vibe. I am seeing parallels with my ex, who has 4 children with 3 women (and there were at least as many pregnancies that weren’t carried to term). And he is Darth. He hasn’t been involved with a woman of his own age since he was in his 30s. Do weigh up all the input you’ve received on here 🙂 Good luck!

  62. LW: You said you may want kids, so I’m going to address some of the parenting issues that you may not be thinking about:

    I did the very traditional thing — marriage, house, baby, i’m still married to the same man, etc. — so I have no idea what it’s like to coparent with anyone who isn’t *right there, every single day*. But I can say that even with the full support and help of my invested partner, parenting is still hard and it’s time/spoon consuming.

    If you want kids with him, look at how he parents his kids now. You want him to be is a great father, which means he should be spending huge chunks of his time and emotional resources on these kids. Because THAT is the kind of person you want to co-parent with. Anything else is just going to leave you gasping for air.

    That said, I can’t imagine what it would be like parenting with someone who invests huge chunks of his time and emotional resources on seven other children by three other women. The logistics alone would be overwhelming. And the best kept secret of adult is this: logistics are a huge part of parenting. (And paper work. Dear heavens, the paper work!) It would be complicated, emotionally, too. (See all the Cap letters about the complexities of step families.) So there’s that.

    Also, what sort of support structure do you have in place for back up? Because you need back up, even in the best of circumstances. You need someone you can call when noro tears through a household and both adults are on the floor, taking turns barfing, and then your toddler comes in and says she’s just barfed all over her night-night bunny and she’s crying and covered in vomit and you need pedialyte NOW because you’re worried about her hydration and you can’t drive to the store (because barfing). My parents and in-laws were not who I could call, but they are for many families. Before I had a kid, I thought long and hard about the who I could count on in a bad situation. If you worry a relationship with this man will alienate your family, make *damned* sure you have rock-solid back up.

    Could you parent successfully under these circumstances? Sure, it’s possible. But you’d have to go into it knowing that you’ve stacked the deck heavily against yourself and against your kids.

  63. I think other commenters have covered all the “have you considered” and “go slow” and “use birth control” pretty thoroughly, so I won’t beat that dead horse.

    It is OK to have a relationship that is just for fun! You are not required to consider every relationship through the lens of “is this leading toward marriage and kids of my own” if that’s not your priority right now.

    I could have almost written your letter 14 years ago if Captain Awkward had existed then. When I was 25, I fell in love with a 39-year-old. He only had one child from one previous marriage though, so that is different than seven, of course. For us, it worked out. We have been married 12 years, we have two kids of our own, and we have a very egalitarian partnership. A lot more so than a lot of people I know who have partners their own age.

    I think people are in the relationships they’re in because they’re getting something they need. For me, I was ready to stop messing around and settle down, I liked feeling wanted and needed, I liked having a family of choice to be part of, and I really liked being able to see what an involved father he was BEFORE having kids with him. I even liked the fact that my husband couldn’t relocate, because I love my city and don’t want to move ever. There are so many divorced parents out there, it’s better that there are people out there who find that lifestyle appealing, rather than seeing it as “settling for less”.

    My parents are like yours, I think, in a lot of ways. Mine were smart enough to know that acceptance leads to access to future grandbabies, and rejection leads to less access, though. Maybe yours are too?

    Go slow, keep your eyes open, and ask the good questions everyone else recommended. In time, the right path for you will become clear.

  64. Awesome advice, CA! Two things I haven’t seen mentioned yet in the comments:

    1) The age-play. As long as you are comfortable with it, it’s ok, and you don’t need to feel weird about being comfortable with it: unexpected things can be fun in mutually-agreed, safe, **consensenting-adult** circumstances where your wants, needs, and boundaries are being respected. That’s 100% cool.

    My concern is that you listed it as one of the things that’s bothering you. If what’s bothering you is just that you’re surprised by the fact that you like it and you worry about What That Says About You, well… it might just say that you have a kink that you didn’t know know about before, and hey, enjoy it! But if something about it just isn’t sitting right, or if the context starts to change (e.g., the frequency increases; it starts to come up in less-fun-feeling situations (i.e., you start to feel like he might be trying to use his age to influence you); he tries to start it or continues it when you’ve made it clear that you don’t want it (right now/anymore/whatever)), or if *anything* about it feels uncomfortable about it *in any way*, that’s when I would suggest that you start re-evaluating what it’s saying about him and about your relationship. As with anything sexual, power-play (of which age-play is a variant) is only fun when the people involved are giving full, willing, informed consent. But if you feel differently at any point, he needs to respect that boundary. If he doesn’t, that will speak volumes about how he sees you and your relationship. (And at that point… leave, please. It’s a really bad sign.)

    2) His ‘poorly-concealed awe’ of your family, and especially of your father. Something about this really isn’t sitting well with me. I can’t put my finger on exactly what – thoughts, anyone? – but I think it’s along the lines of his wanting to perform the life (childhood) he never had, and using you and your family as a way to do this. This is, obviously, doomed to fail because one can’t use other people as actors in the play of one’s life; it also means that you (and your family) would be set up to take the blame for anything that went wrong because you didn’t follow the script in his head.

    Since you said that your parents don’t know that you’re dating, I’m also wondering in what context he’s met your family. Have there been multiple meetings? How have they responded to his affection for them – do they think he’s nice for being interested, or do they seem a little startled by his attempts to bond with them? Does he seem overly-invested in them, for the amount of time he’s spent with them? Again, I don’t totally know where I’m going with this, but I have a gut feeling that there is a thread to pull here.

    And one more thing I have seen mentioned, but want to highlight again: ‘very protective’. BIG red flag there, I reckon. LW, you are an adult. You have what sounds like a safe relationship with your family, you have a job, you have enough self-regard to ask important questions about your present and your future. What does he think you need to be protected from? Do *you* think you need to be protected from those things? What does ‘protection’ look like in an adult relationship between two (hopefully) equals?

    1. I think this is all a very smart comment, especially about the ageplay. Like, it’s wonderful to discover a new kink, but if it starts bleeding over semi-non-consensually into the rest of the relationship…that’s bad.

    2. “His ‘poorly-concealed awe’ of your family, and especially of your father. Something about this really isn’t sitting well with me. I can’t put my finger on exactly what – thoughts, anyone? ”

      Yes, I’m not sure quite what it is about that either, but awe isn’t something I mentally associate with healthy adult relationships. It’s normal for small children to be a little in awe of their parents and adults they admire, but among adults? Among adults it seems a little disturbing (as if you feel the other person is more important or more ‘special’ than you? or even like you fear them?)

      Do YOU feel ‘awe’ for your parents too? Because you describe them as lovely and yet your reluctance to share such a major development in you life with them, and his ‘awe’, both actually look – to an outsider on the internet – more like fear? Or like a kind of distant reverance rather than the trust and respect between two people?

    3. The “Awe” comment got to me because it sounds like he thinks being like her father (from the context of the letter, “a stable loving reliable parent and husband”) is nearly unachievable. Ergo, this boyfriend will not be any of those things.

      1. Aha! Yes, I think that’s it, or at least a big part of it. Adulting shouldn’t be *that* astounding, and it’s worrying that a man in his 40s with seven children and considerable relationship experience still finds it so rare and amazing. He should be there himself by now.

        1. That was what struck me too! “Awe” is a reaction totally out of proportion to LWs dad doing what a parent is supposed to do.
          And exactly why does he find it so amazing? Has he really seen so few responsible fathers in his life that it’s a momentous occasion whenever he meets one?

          Seriously, adulting has been a major challenge for me because of executive function disorders that went undiagnosed for 48 of my 49 years, but I’m not filled with *awe* at the many people I know for whom adulting is a breeze. I may admire them for their achievements, or wondered what secret adulting tricks they knew, but to be in awe of them would be ridiculous.

          It also seems to me very much like Older Boyfriend sees LWs dad as some unattainable ideal that he cannot possibly ever reach. And that right there is something to worry about.

    4. I didn’t get the feeling from the letter that Boyfriend HAS met LW’s parents– perhaps his “awe” of LW’s dad has transpired through hearing legendary tales of his epic feats of parenting, partnership, and adulthood? And where, for many 40+ year-old men this would just be grounds for gentle respect, Boyfriend feels “awe” for this paragon of stability for all the reasons listed above, and also possibly because of LW’s storytelling style?

  65. LW, I agree with what everyone is saying and I can say, from a brief stint of a relationship I had with someone 11 years my senior, I have a few things I now ask whenever I hear about people in relationships with large age gaps (10+ years.)

    1.) Why is someone this much older interested in someone this much younger? I know it seems silly, but I tie it into what the Captain said about observing how he acts toward other women his own age. Is he going after women younger than him because he likes to WOW! them but he’s not actually impressive to women his own age? (And why aren’t they as impressed?) Do women his own age find him to be immature? (Not necessary a deal breaker, but something to be aware of.) Has he tried it with a bunch of other women and they have all, for one reason or another, rejected him? (What might they know about him that you aren’t seeing?)

    2.) Why is he single? If he’s single because his girlfriend of 7 years died in a freak car accident a few years ago and he’s finally ready to date again, it’s a bit different than he can’t keep a woman his own age or that once children are involved he becomes deeply afraid of commitment and must leave. Not to look at things pessimistically, but if a man is more than 10 years older than you and is absolutely amazing, you’d think he’d already be taken. (And most likely by someone on an equal level to him.) I know that sounds a bit mean, especially since you actually might be the love of his life and his one true, but it’s something to consider.

    Overall though, I guess my two cents is to step back and take cues from these other women (not just his exes, but all the ones who interact with him.) They aren’t your competition, but rather people you can learn from. They all have bits and pieces of information about him that you might not have. If 3 different woman have had children with him and deemed him not worth staying in a relationship with, find out why. Because, as the people have stated, his past informs his future. (Unfortunately) You can’t change other people and, try as he might, he might not be able to break his habits for you.

    1. Another aspect to your #1 is that he might just be really immature. I’ve known people (both sexes) who keep dating younger and younger people, but it’s not that they break up because one got older. It seems often that the younger one grows up some, and the older one stays the same age emotionally. The younger one grows out of the immature older one and leaves. The older person then hooks up with someone even younger because that feels like their appropriate emotional age.

      It’s like one is a rock, and the others are a stream passing by it.

      1. A bit off topic, but I love that imagery of the rock and the stream. I’ve seen it once before in a song by SJ Tucker: “better to be the river, not the stone in the middle. best to be the changing water, not the pebble dragging on.”

        Anyway. I hadn’t really made the jump to relationships with that imagery, but it makes sense. I have exes that were so wounded when I left – like I’d betrayed them. Years later, they’re still doing the same stuff they were then – same town, same people, same passions and ideologies. And that’s fine for them, but when I picture the life I’d have had if I’d stayed with them, I feel smothered. Was good for a time, but not forever.

      2. Immaturity isn’t the worst thing in the world, though. Especially if someone is maturing, just at a slower pace, or in a different order (e.g. it’s pretty common for people to develop some aspects of their life and personality first and go back and develop other ones later).

        So to me ‘immature’ isn’t actually an automatic bad thing, just something to be aware of.

        1. I think it’s a little different when there are children in the picture, though. There’s a certain baseline level of maturity and self-discipline you need to be a stable parent, and children don’t wait for someone to finish growing up. Immaturity, taking a different path toward maturation, that’s fine — but going with that is having the wisdom not to jump in too deeply to the responsibility pool while the maturity-swimming skills aren’t fully developed.

        2. There’s also a life-stage thing–the stage of life you’re in, the things that are problems and priorities and goals for you, is not as concretely derived from age as a lot of people like to think. If you do things “backward”, like marry young, go to university later, etc, you will often end up being more compatible with people who are doing the same things and worrying about the same things that you are than people who are “your age”.

        3. I kind of think that Immature + 7 children is quite possibly automatically a bad thing.

          1. It does sound like it is in this case. I was thinking more about there being different types of ‘immaturity’.

    2. “Why is someone this much older interested in someone this much younger?” Maybe for all the reasons anyone is romantically interested in anyone else!
      (I’m in a long-term relationship with a wonderful man who happens to be 23 years older than me, and towards the beginning my mom kept saying things like, “what do you want out of this kind of relationship?” as if it had to be fundamentally *different* from relationships between people the same age. What I wanted was love and humor and support and intellectual stimulation and a best friend who also made me feel all mushy (i.e. all the things people generally want out of a romantic relationship), which is what he wanted too, and that’s what we continue to give each other!). If he exclusively dates much younger women, that might be something to wonder about, but there’s no indication of that in the letter.

      I don’t have any advice to give about the 7 kids bit, but I want to chime in for team ‘Age Difference Relationships Are Not Inherently Creepy, Same Age Relationships Are Not Inherently Healthy’.

    3. Agreed with the #1, this is always my first thought in such large age gaps. But some thought about #2.
      Pondering a partner’s previous relationship status is all well and good if said partner has made it clear that they prefer to be in a relationship at all times. But people can – and have! – chosen to be single, yes even for ten whole years!! It’s not a matter of being ‘taken’, it’s a matter of /choosing/ to be in a relationship.
      So while OP may consider asking him about it, he very well may have chosen to be single this whole time and that’s okay too.

      1. He hasn’t chosen to be single, though, if he’s managed to have 7 children in the past 20ish years, even if you use a loose definition of single that includes casual or short relationships (without adequate birth control?) One child with someone could be an ‘accident’ but 5 in a row is a long-term relationship.

        1. I’m not talking about his past relationships, I’m talking about the implication that he wasn’t “snatched up” in the time that he was single. Obviously he was single before dating LW, that’s the point of time I’m referring to.

    4. Many men express contempt for women who are middle aged and older. They only see young women as desirable, as any middle aged woman who has tried online dating has discovered. There are men in their 50s and older who will only consider dating a woman at least 15 years younger.

      1. Some men do, yes. Some men also have to date younger women because women with any experience whatsoever won’t put up with the shit they try to pull. Some men don’t have a pattern of dating any specific age but meet someone much older or younger who just really does it for them. There’s such a variety that trying to generalize isn’t all that useful.

    5. CeeCee, I agree with most of your comment, but this part really rubs me the wrong way: “…if a man is more than 10 years older than you and is absolutely amazing, you’d think he’d already be taken.”

      Regardless of age, whether or not someone has found a long-term partner isn’t a referendum on their awesomeness–just look at all the letters from “terrifyingly amazing” people who are struggling to find someone. Sometimes it’s just sheer dumb luck, and not-so-nice people find partners all the time while wonderful people are single through no fault of their own. And, as pyn mentioned below, sometimes people choose to be single for a period of time, which is also a perfectly valid choice.

      As someone who spent most of my life single until I found my (amazing!) partner 4 1/2 years ago, and could never quite shake the feeling that there must be something wrong with me, I just really, really, really bristle at the idea that being single says something bad about a person’s character.

      I agree that it would be a good idea for the LW to examine why her boyfriend broke up with/divorced the 3 mothers of his children, and look for patterns that might also be playing out in her relationship. But it’s possible to do that without assuming that there must be wrong with anyone of a certain age who’s single.

      1. Yep. This for me too. For what it’s worth, I think one of the reasons I’ve stayed in an unhappy relationship much too long in the past, is the idea that being single was somehow shameful. That not being married at x age would mean that people would look at me strangely in the future and wonder what was wrong with me.

        Dear LW, I’d say focus on the good/bad of his relationship with you. Seven children, three exes (or any other past stuff) doesn’t have to be a referendum on his character for it to be something you don’t want or can’t deal with.

      2. I truly didn’t intend for it to be as bristly of a statement as it may have been taken (and can see, in retrospect, how it was enough of a generalization to be taken as such). I don’t think there’s anything wrong or less awesome with being single as opposed to being taken or that it necessarily says anything about a person’s character, but rather just something to consider.

        While I’m willing to bet that 95% of the time it doesn’t say much about a person, there’s still a small chance that it might. And if the reason they’re single isn’t a negative reason, that’s a plus!

        I guess it’s just always something I’ve suggested friend’s consider because (at an age where a lot of people in my demographic are settling down and it feels like a good partner is hard to find) I’ve have had more than one friend date someone who ended up being more of a negative than a positive. And in those situations, when they’ve looked back on these people there have been red flags right from the get-go — usually evident when they consider reasons for their last relationships ending. (In these cases it was usually problems with things like substance abuse or abusive personalities, which, if that’s why a person is single, is a good thing to consider.)

        Again, I certainly didn’t mean it in a way to assume that being single meant anyone was any less than awesome, just that there are times when it’s an indicator of a bigger, more serious situation to consider.

  66. I saw the film Anomalisa last night and it really reminded me of the Captain’s advice to be weary of someone who talks about the relationship as a ‘new beginning’. SPOILERS SPOILERS SPOILERS – it’s an animated film where all the characters apart from the protagonist are voiced by the same actor, which reinforces the sense of his loneliness – he’s a writer in Cincinnati to give a speech, he’s unhappy in his marriage and can’t relate to anyone. He meets a woman who’s the only other person in the film who has her own voice, and immediately falls for her because of it. She’s younger than him and a huge fan of his book, so all their interactions are about her fangirling over him in awe while constantly putting herself down in comparison to him – she feels very insecure because she has a small burn scar on her face, and she calls herself dumb, ugly, boring etc. They have sex and he starts talking about leaving his wife for her, how she’s different from everyone else and he needs to be with her. This all takes place over the course of a night. The next morning he starts becoming controlling and hyper-critical of her perceived flaws, and also hearing the normal voice along with her voice when she talks, and I thought he may genuinely be lonely, but he definitely won’t cure his loneliness by idealising someone as the solution to it because he can only relate to her because she’s vulnerable and worships him. Or at least that’s my take on it – it’s definitely a film that can be interpreted in different ways (including as just another self-indulgent tale about how hard it is to be a rich white man who’s a jerk to everyone – I loved it but I can see why some viewers would hate it.) Anyway, I’m not saying the LW’s relationship is like that film – I can’t disapprove based on the age difference alone because I’m attracted to older men myself. LW, if you’re happy and feel respected and loved and treated as an equal, then the relationship works. But there can be problems in any relationship, and significant age differences can create or add to those problems, and the film was a really good illustration of why a particular relationship dynamic where an older (usually male) person becomes convinced that dating a younger (usually female) partner can cancel out their whole life before they met them and fix all their problems doesn’t end well. I think this blog post by Cliff Pervocracy about some of the hall marks in a healthy relationship is really good: http://www.pervocracy.blogspot.co.uk/2012/07/green-flags.html. And this website has advice on spotting red flags in abusive relationships, if that’s something you think you might need: http://www.helpguide.org/articles/abuse/domestic-violence-and-abuse.htm

  67. “3) MY kids. Still can’t decide if I want them, but I definitely want the option. He stated at the beginning he would never have more kids, but hinted recently he ‘might not be done yet.’ Part of me really likes the idea, but another part is horrified at being the 4th mother of his children and asks me wtf I’m doing with my life.”

    This makes my eyebrows go up. Especially the part where he changed from a definite “never” to a “maybe I’m not done yet”. This could just be the LW’s phrasing, but in light of his existing children and past relationships, phrasing it in terms of his wants and desires contributes to my discomfort.

    This dude likes procreating – he REALLY likes procreating. This is not in question: he has 7 kids, and he “might not be done yet” (if he was really done, snip and no worry). So let me suggest an alternative narrative to the Captain’s about him possibly being good at beginnings but not so much at middles or parenting (especially relevant if he’s a GREAT parent): dude views women primarily as breeding partners. He has all the kids his partner wants with one (one each for the first two, five for the third, if I’m counting correctly), and then he dumps her in search of someone else who wants to gestate his offspring, becasue procreating is his top priority. (I just realized that to some extent this does match the Captain’s proposed narrative, but the difference is that in mine he would likely stay with a woman who wanted to keep gestating new people.) It would also explain pivoting to dating a much younger woman – you are likelier to be able to procreate for longer, LW. I don’t have any direct evidence that this is what’s going on, but it fits with the pattern of behavior, so it’s another possibility to consider.

  68. About your parents: You seem sure your parents would see this relationshil as a negative thing, but what I would ask myself is, do you think once they got to know him them would be reassured? Do you think over time, seeing how you felt and seeing you happy around him, they’d slowly come around and understand?

    And when you say they’d be ‘crushed’, why do you think that? Do you imagine it more as then being worried about you? Or feeling like there was something embarrassing about thr situation. Or making a moral judgement about having children out of wedlock or getting divorced?

  69. I dated a man at work who was 15 years older and was my direct supervisor. It, too, was a secret because of our boss/employee status. So, from that 8 year, long-ago and ultimately unsuccessful pairing come these questions:

    1) Is he your supervisor or boss? If so, there is built-in inequality between you.
    2) Are you violating company policy by dating him? This can have unpleasant repercussions for you at work.
    3) What do your co-workers think of him? Do they know about those 3 wives and 7 children? If not, why not? Did he date anyone else at work and what do you know about that?
    4) Has he sought therapy? Why is he recreating his birth family drama with you and his previous wives? He will continue this psychological quest unless he understands it. You should not try to fix this for him! Read that again! Not your job to fix it!

    You’ll do what’s right for you but don’t do anything with closed eyes. Remember that words and actions should match.

    Best of luck, LW.

  70. OP, I see a lot of red flags, but I also see you trying to artificially keep a relationship in the honeymoon phase by keeping it a secret. I think you should come out of hiding and be open about your bf with your family, friends, coworkers, etc. I believe that that process will give you the answers you’re looking for. Relationships are really forged where the rubber meets the road, IMO.

    1. Yes, this. “I can’t tell my parents” and “maybe we’ll have a kid together” is not a circle that can be squared, LW, unless you’re willing to cut your parents out of your life.

  71. In addition to all the excellent advice so far, I would add simply this: there’s really a lot of factors here.

    Imagine all the variables on a big board like those complicated physics equations, and its complexity can be simply overwhelming. I think that is significant, because LW is being asked to have an extraordinary juggling ability. It is the age gap AND the children AND the exes, who are not mentioned but have extraordinary power when there are children involved. Not mentioned is the finances and time, but I cannot see how that is NOT a factor, moving forward.

    On a dating level, this could be a fine relationship. But to build a life with all these moving parts and then the prospect of adding even more complication with theoretical future children sounds like a lot to juggle for a person who is a couple of decades older than LW. Much less the age LW is at, which should be a time of growing and gathering abilities, not just extracting them.

    It is marvelous to be regarded as marvelous for one’s abilities to meet daunting challenges, and this relationship certainly qualifies. But we have the right to invest all this marvelous energy into our own life.

    That is the danger for LW.

  72. LW, it feels like the most important point in your letter is the one kind of buried at the end: you’re turned on by the dynamic between you, and you feel kind of weird about that. It’s going to be very hard for you to sort out “my head is telling me one thing, but my pantsfeelings are telling me the opposite” when you’re still coming to grips with your pantsfeelings for this guy.

    You’re both adults; you don’t have any kind of past where he actually had an adult/child or place of power over you; you’re not dependent on him for the necessities of life. I think it makes sense to ask yourself WHY you find this interesting to see it if is IS coming from a problematic place, on either end of the relationship (in ways that CA and other commenters have set out very well). If it’s not, then maybe don’t worry about it being weird, and focus on all the other issues in your relationship.

  73. I get that you feel that your parents would be worried, even disappointed maybe? But where does ‘crushed’ come from? And do you think they would change their minds over time as they got a chance to get to know him? If this is something you do really want, and if your relationship with your parents is also valuable to you, sooner or later you’re going to have to let them get to know each other. If both he and they are as great as you describe them, then they will likely learn to get along.

  74. Yeah, there’s a lot here that could go wrong. I have seen relationships like this work, rarely: my grandfather was thirty years older than my grandmother, had been married multiple times and had I believe five children already when they got together; they stayed happily married until his death and had another four children together and by all accounts everything worked out fine (he did not, however, have a good relationship with most of his older children, so that’s a thing to consider). But there are a lot of ways it can go wrong. He has responsibilities to his existing children that you need to take into consideration if you’re considering joining finances or living arrangements with him, let alone having kids with him. You cannot marry an involved parent and have nothing to do with their children; if he’s not an involved parent, then you should take that into consideration before you have kids with him.

    The age-play thing is not an issue in and of itself, but if it bleeds out into the rest of your relationship that can become problematic. I’m a bit more bothered by him being in *awe* of your stable family of origin. Awe is a bad platform to build a stable familial relationship on.

  75. I had commented, and it’s not appearing… not sure if it was deemed not relevant enough because I was +1ing solid age difference relationships and didn’t address the LW’s specific situation?

    1. Third option: Captain is not always by a computer to free things from spam trap or mod queue.

      1. Dear Captain,
        I left a comment back on March 24th as I am in a long-term relationship with someone 30 years older me, and I wanted to provide some thoughts based on this experience. I am not sure if it is still stuck in the trap/queue or if you decided it was not adding to the discussion… So I am also not sure if I should try resubmitting it.

          1. Thank you for responding! That’s so strange – I tried posting it again, slightly edited, and it completely disappears. I will try breaking it down into 2 shorter ones, may that’s part of the problem.

          2. Like unlikely quest, I also notice this behaviour.

            As a poster, is there a way to note whether your comment has gone through (but is awaiting moderation) like on many sites? Or whether it has just blackholed?

            Once I thought my comment had been eaten, so I resubmitted…presently I returned &they’d both been approved. So I don’t know whether to resubmit and risk dupes, or not. (I hope this makes sense?)

            I tried to work it out by the url after I’d hit submit, because it looks like it will link directly to a comment, but since my comment doesn’t show, the whole page loads again (starting at the top, annoyingly).

            I hope this info is useful. Damn – I hope it reaches you!

        1. I will try posting my comment here. Let’s see if this works:
          As someone in a stable enduring relationship with a man 30 years older (it’s now been about 6 years total, 4 of them living together), I would like to echo all of Captain Awkward’s questions, as well as concerns about power dynamics raised by other commentators as well. I cannot comment about children, and I feel other commentators discussed this issue in detail, but I wanted to comment on the relationship overall. Me and my partner have lasted because we are extremely aware of these questions and our answers to them.

          We keep track of potential changes to these answers – that is, we keep having these conversations, on and off, when it seems relevant. For example, we discussed and agree that this relationship works very well in terms of overall compatibility and stability in day-to-day matters – a consideration that over-rides chemistry by significant margin. It always makes sense to be aware of how your differences help things and how they complicate things. Age differences seem to add extra layers to these considerations that are important to explore, partly due to differences in life-stages/goals, both in the beginning and as the relationship continues to evolve.

          As part of these questions, we also talked about “This is great now – but what happens in 30 years?”. We discussed our hopes and our fears, life and career stages, expectations, etc. And while we have not made exhaustive plans, we have an idea of how to handle the differences and fears, both immediate and in the future.

  76. LW, what do you really, truly feel when you think about the future with this man? Hopeful, or worried? Excited about the relationship’s potential, or stressed with the sheer logistics of trying to juggle 7 kids and 3 ex spouses, and dealing with the possible fallout from telling your family? What does he say when you talk to him about your concerns with being open and honest to your friends, colleagues and your family about the relationship? Why would he say that his young kids are not your responsibility, when he is bringing them to your house and you are feeding them? That’s a mixed message. If you are indeed on the road to a long-term commitment, his kids will become part of your responsibility, simply because you will be around them frequently as their dad’s partner. The fact that he stated at the beginning that he didn’t want anymore kids, yet now states that he could be persuaded to change his mind, smacks of “I better say I am open to having more kids or this woman who is more than a decade and a half younger than me (and might want a family) will dump me for a younger dude with less baggage.”

    Speaking of, do you think he is a good father? Does he make time for his kids, separately and as a tribe? You mentioned his ex is the primary caregiver for five of the kids (holy shit that woman must be exhausted), so what role does he play in their lives on a daily/weekly/monthly basis? Does he actually engage with his kids, take them places, teach them things, encourage and console them with they need it? Pay child support? Why did he not go for shared custody? If you decide to have children with this man, these are questions you need answered, because if past is prologue, you may wind up as a single parent, competing with seven other children (and three other exes), who are entitled to time, money and affection from their father. Are you prepared for that? If not, that’s ok! It doesn’t mean this relationship is over, or you’ve made a terrible mistake. It just means that, in due time, perhaps this relationship will run its course, and that’s okay. It’s okay to enjoy what you have now, enjoy the companionship and company, and know that it won’t be a long term thing.

    Only you can decide what you are willing to sacrifice for this person. He may be worth it! Or, he might be a dude who dates much younger women because it lets him avoid responsibility for his past mistakes, and allows him to control the narrative. You know him, we don’t, so take what we write with your own grain of salt. I wish you luck in whatever you decide, LW.

  77. “I love my parents so much but they are pure-hearted, frankly naive, upper middle class, white collar conservatives ” – LW I’m going to side eye you calling your parents “naive”; you know them way better than I but yet, while it’s easy for a worldly 20-something to THINK they are more experienced than straight laced parents, do remember your parents have decade(s) more experience living with you, including having you and raising you. Maybe they have different tastes and interests but I doubt they are more naive than you, and I agree with the other posters that if you’re really thinking this relationship is for the long haul you will need to tell them and if that scares you then think hard about why.
    I say this as someone who was a worldly 20-something not too long ago, with loving and supportive (and also very straight-laced) parents, and married someone my parents weren’t thrilled with. It’s worked out but I could pretty clearly articulate where the gap was; different goals and expectations (they pictured someone dedicated to their own career, I wanted someone dedicated to me/supportive of my career). If your BF is really a good guy for you with a rough past, and your parents are reasonable people, they will come around. You don’t have to tell them right now, but if you get to the point that you are thinking of a major commitment (moving together, merging finances, reproducing) then you really should! (cases where parents are abusive/toxic excluded, but LW implies this is not the case)

  78. There’s already been excellent advice given by the Captain and the rest of the Awkward Army, but this topic has been bugging me, so I’m going to add my 2 cents…

    The fact that he was your former boss *plus* the age difference makes me cringe. Either one of those things happens often enough in the workplace, but both together? It screams “Ego Trip” on his part. And the ageplay and the “protectiveness” hint at control issues — not necessarily in an abusive sense, but that can be a possibility. [Example: My own father has a fragile ego and does not manage equal-level relationships with adults very well. Unsurprisingly, he really enjoys the time he spends with his grandkids (who have to do what they are told), and looks forward to seeing them more than his adult children (who long ago stopped doing things because he told them to).]

    LW, you realize that by continuing to be involved with this man, you will have to comprise, nay, sacrifice so very much of your own youth and life experiences for this relationship? I suspect you do, but just in case it’s not quite on the conscious level, I’m putting it in writing. This man has already had a lot of life experience, and unlike many men his own age, has 3 former wives/partners and 7 children to show for it. If you remain involved with him, are you prepared for the resentment that he got live his youth while you had to sacrifice yours to take on all the responsibilities that come with instant family x3? (Or x5, or x7… whatever.) Really, I think you SHOULD feel resentful about what you would/will give up for him. I think regardless of your parents’ conservative views, they would be crushed because of what you, their daughter, would give up in terms of opportunities, life experience and happiness to be with this man.

    Another thing that bugs me… I question how much he’s willing to commit/sacrifice/compromise to really make a relationship work, as well as consciously choose to do what is best for his family. Seven kids with three moms… I have serious doubts about his willingness to do the hard (emotional) work necessary for a committed relationship and to put the well-being of his spouse/partner and children before himself when it matters most. I don’t know him and his values, but on the surface, it looks like he made (or abdicated?) a number of important choices multiple times already without a lot of thought to the futures of everyone involved. If that’s the case, he will surely continue in that mode.

    As the Captain said, what you choose to do is entirely up to you. (Although I obviously would advise you to not consider anything long-term or serious with this man.) I just want to leave you with one last thought, LW — feelings change. Sometimes suddenly, with or without reason, and sometimes they just evolve over time. The way you feel when you are with him now will not always feel this way. More importantly — he is not the only man who will only ever make you feel as wonderful as you do now with him. There are many other amazing men out there you can potentially feel just as happy with, maybe even more so. Maybe not right now, but just remember there are many potentially fulfilling relationships that do not come with so many challenges and sacrifces. Good luck to you, whatever you decide.

      1. Oh man…. my bad! I got confused with the previous letter which was also a work situation. That one is the one with the former boss.

        My apologies for not double-checking my reading comprehension before posting!

  79. My grandfather married a woman a year younger than his eldest biological child. He’d been married three times previously, had one child with each of his previous wives, and two step-children from his first marriage. My mom, his eldest step-child, is 47, and my youngest uncle is 14. He has 8 children total, three with his current wife. And you know what, their relationship seems great.

    It took a while, but we’re all over the age difference. My mom and aunts and uncles are true siblings to each other. But it only works because his wife has happily stepped into a life with a lot of history in it that doesn’t involve her, and because my grandfather worked through the crap that ended his previous marriages (some of which involved choosing the wrong partners, but that was still his wrong choice).

    The thing is, even though I have an example in front of me of a situation where this kind of relationship worked out, I still couldn’t recommend it. You only have one life, and you can only control a little of what happens in it. Why choose such a hard path, one that limits so many of your options?

  80. One other thing that I would add is that while all sorts of age differences can work in a relationship, one of the things that I’ve seen be the hardest is when you are in a different stage in life. Being in high school, being in college, being in first jobs, being in a career, being in child-raising mode, being in retirement…. It’s not so much the exact age that I’ve seen be an issue, but rather where you are at. That’s part of why a 3 year age difference can mean a lot if one person is in high school and the other is in college, but may not matter at all if you’re both in the working world. This is of course not a 100% firm rule, but it’s a good rule of thumb to try and be more or less in the same life stage.

  81. LW, have you heard of New Relationship Energy (NRE)? It’s that giddy everything-they-do-is-awesome light-headed feeling, the head-over-heels-in-love-with-them feeling at the beginning of relationships. It’s our bodies trying to get us to settle down and, ahem, pass on our genetic material ASAP and it causes us (as human beings) to behave a bit irrationally and to overlook or minimise potential problems or mismatches. It lasts between 18 months and 2 and a half years.

    The NRE stage in a relationship is really fun and good and it’s the part that almost all romantic fiction focuses in on. It’s not good or bad to be in this stage! It is however something to be aware of because the NRE stage is not the best time to make important decisions like “whether or not to have a baby” or “should we get married”.

    What I’m getting from your letter LW is that you are likely feeling NRE and you are *also* aware of potential problems in the relationship going forward. What I’d suggest you maybe think about is this: are you aware of these problems because you’ve recognised that you are head over heels and might need some help seeing things clearly or because *the problems themselves* are big enough and difficult enough to have burst through your bubble?
    I can’t tell you which is true for you or what you should do with the information because I’m not you but I think pondering this might help you.

    Something else that struck me from your letter, LW is that it seems that *you* are considering making this relationship long term, possibly cohabiting, maybe marriage, maybe offspring but there’s no indication that you and your boyfriend have talked about this. Hinting that he “maybe isn’t done yet” doesn’t count because it allows him a lot of plausible deniability – he’s not said upfront that he *would* consider having a child with you and he’s not stated upfront that he *wouldn’t* either. It sounds to me like he perhaps doesn’t want a child at all but thinks saying so would mean losing you so instead of talking plainly and honestly about what is and is not likely to happen and the practical implications he’s just hedging his bets. He could say that he’d “maybe” have another kid *for the rest of his life* so if this is important to you, you may want to look for another partner.

    Lastly, I want to echo the Captain and say that relationships can be short(er) term and still be good and important. Some of the people who helped me grow hugely as a person were my partners for only a few months. Some of them are still in my life as friends, others are not. Your happy ever after doesn’t have to be with the same person the whole way through.

  82. LW, I think your own words are pretty telling here.

    “I CAN’T. I love my parents so much but they are pure-hearted, frankly naive…”
    As opposed to…? Yourself? If your upbringing was very strict and religious, it might be worth looking at how you feel about yourself, or even talking to a therapist. Being in a relationship doesn’t mean you are less pure of heart. Even a relationship with an older guy, with kids, and a history, etc etc. YOU are not doing anything wrong for having feelings, here.

    “…it would crush them… (I’m the black sheep atheist though, so I’m kinda used to that).” This makes it seem a little odd that your BF looks at your family with “awe”.

    “It took a while for me to put aside my prejudice and accept that he came from an abusive, broken family… STILL THOUGH. Guess I still can’t put it all aside…”
    Being wary of someone with a string of broken relationships is not prejudice. And having a broken home doesn’t necessarily explain his choices. I know plenty of people who didn’t make the same choices as their parents. I think part of you knows this. It’s obviously still bothering you, and the way you write this, it sounds a little like you’ve been coached on how you’re ‘supposed’ to feel about him. I hope I’m wrong, but this stood out to me.

    “He stated at the beginning he would never have more kids, but hinted recently he “might not be done yet.””
    People are allowed to change their minds over time. But if this is a pattern for him, saying one thing and then changing his mind to another, that might be something to look out for. For example, saying the kids aren’t your responsibility, and then you hang out with them and play games with them anyway. Do you think his intentions are good? Do you think he’s truly saying what he means? What do you think has changed his mind, here?

    “Part of me really likes the idea, but another part is horrified… and asks me wtf I’m doing with my life.”
    “What’s happening? Is my situation okay or not?”
    You are the only one who gets to decide if your situation is okay or not. I suspect you wouldn’t have written in if you truly thought it WAS okay. You seem happy, you really do, but you also seem dazed and confused and worried. Those nagging feelings in your gut haven’t gone away after a year, or maybe they’ve been getting worse? But you get to decide what this relationship is worth to you. You have a “gentle, loving, extremely witty, very protective” partner… and being with them makes you feel “conflicted” and worried about your future. Is that okay, or not? Those random hugs and flirty moments and smiles are just as real as the worry and the fear and the confusion. You’re the only one who can decide what’s okay [i]for you[/i], LW.

  83. As someone in a stable enduring relationship with a man 30 years older (it’s now been about 6 years total, 4 of them living together), I would like to echo all of Captain Awkward’s questions, as well as concerns about power dynamics raised by other commentators as well. I cannot comment about children, and I feel other commenters discussed this issue in detail, but I wanted to comment on the relationship overall. Me and my partner have lasted because we are extremely aware of these questions and our answers to them.

    We keep track of potential changes to these answers – that is, we keep having these conversations, on and off, when it seems relevant. For example, we discussed and agree that this relationship works very well in terms of overall compatibility and stability in day-to-day matters – a consideration that over-rides chemistry by significant margin. It always makes sense to be aware of how your differences help things and how they complicate things. Age differences seem to add extra layers to these considerations that are important to explore, both in the beginning and as the relationship continues to evolve.

    As part of these questions, we also talked about “This is great now – but what happens in 30 years?”. We discussed our hopes and our fears, life and career stages, expectations, etc. And while we have not made exhaustive plans, we have an idea of how to handle the differences and fears, both immediate and in the future.

  84. As someone in a stable enduring relationship with a man 30 years older (it’s now been about 6 years total, 4 of them living together), I would like to echo all of Captain Awkward’s questions, as well as concerns about power dynamics raised by other commentators as well. I cannot comment about children, and I feel other commentators discussed this issue in detail, but I wanted to comment on the relationship overall. Me and my partner have lasted because we are extremely aware of these questions and our answers to them.

    We keep track of potential changes to these answers – that is, we keep having these conversations, on and off, when it seems relevant. For example, we discussed and agree that this relationship works very well in terms of overall compatibility and stability in day-to-day matters – a consideration that over-rides chemistry by significant margin. It always makes sense to be aware of how your differences help things and how they complicate things. Age differences seem to add extra layers to these considerations that are important to explore, partly due to differences in life-stages/goals, both in the beginning and as the relationship continues to evolve.

    As part of these questions, we also talked about “This is great now – but what happens in 30 years?”. We discussed our hopes and our fears, life and career stages, expectations, etc. And while we have not made exhaustive plans, we have an idea of how to handle the differences and fears, both immediate and in the future.

  85. I scanned the comments and apologise if this has already been mentioned. HOWEVER, I want to address a part of your letter, LW, that jumped out at me.

    “The ageplay. As an example, if I tease him too much, he’ll tease back and say that I’m grounded unless I stop. Usually the convo has a sexual overtone. We’re just joking and honestly I really like it. But the fact that I like it makes me feel weird.”

    This is perfectly normal. I’m involved in my local kink community and practically *EVERYONE* in my area is into ageplay. Which makes me seriously uncomfortable for my own reasons that have nothing to do with them. Some of those reasons are from preconceived notions that I’ve gotten from general society regarding ageplay and people calling others ‘daddy’ or ‘mommy’ or displaying that type of relationship. Some of it is just it’s not my kink. Actually a LOT of it is the latter. HOWEVER, ageplay with sexual over or undertones is an ok thing to have in a relationship as long as the consenting adults in the relationship are ok with it and all on the same page (both in and out of the kink community).

    Otherwise, I’m with the captain here on advice. You are the only person who can make the decision if the relationship is good or not for you. Think about what the captain and other commenters have said and act accordingly. I wish you all the luck.

  86. The thing that worried me most in your letter — and I have a feeling it has stuck in your mind too, since you mentioned it — was the eldest daughter helping you out with birthday ideas for him shortly after you met. She loves her dad, and wants to please him, and that’s great, that happens in loving families. But in loving families that are also safe families kids are allowed to express feelings like… standoffishness, disinterest, dad’s new friend is his friend and not my friend, I’ll be polite but that’s it. The “two little ladies conspiring together to please papa” dynamic is one that divorced dads who are not actually that great at dadding produce; those dads are also not in the long run good at relationshipping. They can be super-charming, and can generate a lot (a LOT) of misplaced hopeful loyalty and eager-to-please behaviour and squashing of hurt and anger and doubt.

  87. Captain and the Army have it covered, but one further suggestion. If you think you want to have a child of your own someday, one of the best, most important things you can do for that child, is to chose his or her father well and carefully.

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