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#269: Anxiety, chemistry, and second chances.

Johnny Cash & June Carter Cash looking all romantical and stuff.

A strong argument for the second-time-around.

Dear Captain Awkward:

I’m caught in my own head and could use a guide to get out of it. There’s a gentleman who’s recently come back into my life. We first connected two years ago when he was separated from his (second) wife and while we talked all of the time and hung out a bit nothing ever came of it datewise. He faded out on me and it was a bit painful, last I had heard he had gotten back together with his wife to see if things could work.

They obviously could not. He’s now living on his own (well, with his kids) and found me on a dating site. He apologized for disappearing (understood, lots of shit going on, obviously! Had I known, I wouldn’t have gotten at all involved/interested the first time around) and I generally feel like people deserve a second chance. We’ve started talking again and hanging out as friends but the potential for more is there. We’re both still insanely attracted to one another and get along like gangbusters.

We’ve tried talking about where things are headed and how we should approach whatever kind of relationship (friends? more?) is developing, but I think we both make it more confusing when we try to use our words. And not to sound condescending but I’m not sure that HE knows what he wants/needs at this point. He’s only been separated about 4 months so far and living on his own for the first time in a long time. He wants to just take things as they come and go with the flow. My heart agrees but I’m afraid I’m (we’re) going to be too intense too soon after meeting up again and clicking so well..and then he’ll freak out a little while down the road. I like this guy too much for him to be a booty call or friends with benefits, I can do just friends but then both of us need to turn the flirting and romantic overtones WAY down, stat. I’m not sure how to reconcile what he might need with what I want or how to approach the whole damn thing. I also don’t know what words to use or how to use them when we end up just talking in circles and end up back at ‘I like you, you like me, let’s see what happens’.

French toast from Cafe Selmarie. Photo by your host, Captain Awkward

Robert’s Rules of Pants: Your pants want you to have sex and then eat delicious breakfast.

I’m worried it’s too soon for a full blown dating situation (which is ideally where I’d like to see this go, in time), that he might need to go out and date oodles of people or maybe just be on his own and be cool with that before I get involved with him. When I’ve suggested it he says that I make it hard to want to go out and meet/date other people. So do I absent myself from his life for a certain period of time? Then again, you’d think that at 40some years old he would know if he ought to get involved with someone…but his track record says otherwise…but every situation is different. Right? Aaaarg!

On the other hand, I’m 30+ years old and also wonder if I should be looking for a more ‘suitable’ partner even though I really like everything I’m getting to know about him. Is liking someone for personality and pantfeelings enough? I know we all have baggage but is this (two kids under 13, two ex-wives, financial um pinchy-ness and general lack of free time due to aforementioned kids and ex-wives) biting off more than I can chew? Maybe I’m just overthinking all of this and need to follow my heart and tell my stupid brain to shut up and enjoy it for what it’s worth and deal with any fall out and heartache that may occur or do I let logic lead the day and cut my loses before I know what they might be? Or is there some third path I’m not seeing? Any insight from you or the wonderful commentors would be appreciated. Thanks!

– Stupid Brain

Dear Stupid Brain:

Looking around at my extended friend-family, I can tell you that sometimes it’s the second or the third marriage/very serious relationship that’s the charm. Great love stories can start when shit is all complicated and uncertain, and divorced people deserve/need/can be awesome at giving love, too.

I think this is a question about how to figure out when your anxiety is protecting you from potential sadtimes and when your anxiety is just anxiety that’s getting in your own way.

Because if you were having fun and feeling 100% awesome and hopeful about this thing, you wouldn’t be writing to me right now. You’d be too busy having sex with your new hot boyfriend. And your brain would deal with the questions you have about the future – How is this all going to work out? Am I going to have to become someone’s stepmother? – by seconding the motion made by your pants. Your pants move that you stop thinking about this, have sex again, and eat French toast. Delicious, delicious after-sex French toast with berries, or maybe an omelet. Maybe the anxiety is just anxiety, in which case: Your breakfast awaits you.

Don Draper and Megan Calvet: They can get to know each other after the honeymoon.

They can get to know each other after the honeymoon, right?

But let’s say there’s a really good reason you don’t trust yourself or your future around this guy. His stats show that he’s really good at getting women to marry him and let him put his babies in there. Stated in the most positive light, he’s a romantic and an optimist and those people are charismatic and fun, fun, fun to be around and you are not stupid for wanting to be a romantic and an optimist, too. I understand why you are fascinated and also thinking “Hey, those other women felt exactly like I do right now, and it didn’t work out for them. So what’s going to be different this time?

His stats are what they are and they don’t automatically make him unsuitable as a partner, but it’s worth poking about in his history a bit. Does he have self-awareness about why his relationships ended and his part in the whole thing, or is it all the other person’s fault? Does he take on too much guilt about it, presenting himself as this tragically fucked up person who doesn’t deserve you and do all these

A cat sniffs a Darth Vader mask.

Does this smell like a Darth Vader situation?

conversations end with you comforting him about how no, really, he’s awesome? If so, beware: HERE BE DARTH VADER. He will suck the life out of you and manipulate you into comforting him the entire time he does it.

How did he treat his exes on his way out of the marriages? Were there consistent dealbreakers or sticky wickets between both that you can also see being sticky wickets for you? Do you feel like he’s using you as a therapist and/or soft landing so he doesn’t have to deal with being alone and figuring out his shit? It’s an uncharitable thought, but I’ve done enough dating-in-my-30s to have seen it more than once: Some people are crap at being alone and when one relationship ends they look immediately for another one with a benevolent girlfriend-mommy who will pet their hair and tell them they are smart and pretty.

Maybe the most helpful thing you can do for yourself is to forget the idea of “suitable” or what “should” happen or the idea that you, by withholding your fine booty for some necessary period of mourning and self-discovery, can magically control whether he can be a good partner for you down the road. Because you’re already the expert here. You know the guy. You know his history. You know (or are in the process of figuring out) your own needs and wants. More importantly, you know your own history WITH HIM.

How did he treat you when he disappeared and left you feeling crappy before? I know you didn’t actually date, but what expectations & hopes did he put out there before he disappeared? What’s different now?

You worry (with reason) that he’ll be stretched emotionally, temporally, and financially. Let’s flip that around for a second and make it about your needs and whether he can meet them. Will he be there for you in the way you need a partner to be there for you, or will you always come in second to his responsibilities? When you date someone who has kids, you sign up knowingly and willingly for coming in second to those kids. Is that going to be enough for you? Is there something concrete he could do balance things and to make sure you are getting the time and attention that you need?

Now for the very concrete advice part:

First, you’re absolutely right. You can’t be “just” friends. You’re not friends now.  Your pants are going to literally catch on fire any second. So either jump into the big-time sexy serious intense relationship you’re right on the edge of having and accept the risks and the consequences, or say a firm and total goodbye.

Second, don’t make it about whether he’s ready. It’s a canard. It’s patronizing. And you can’t control that for another person. The question is: Are YOU ready? Are you excited? Do you think you’re going to be happier with him than you were without him?

Template for a pro/con list.

Pro: Raging ladyboner Con: Can’t stop making “pro” and “con” lists about him.

Third, should you need it, this is what a firm and total goodbye looks like: “I have too many anxieties about the future to want to date you right now, and too many pantsfeelings to be able to sustain the lie that we’re just friends. I’m tired of going around and around about this question, so I’ve decided that it’s better for me if we don’t talk anymore. I wish you the best.” And then you delete his number from your phone and purge your e-life of his flirty e-messages and you do not find reasons to run into him. You go out and you meet other people and do your own thing.

FYI, a Darth Vader will hear that speech and he will take it as a sign to try to put his penis in you now, quickly, before you get away. He will want to hug you “one last time” and that hug will last a little too long and it will get all handsy in there and it will feel really, really good. And the next day you might have delicious breakfast, but you might also have an expensive visit to the pharmacy to purchase Plan B and the 150th long circular talk about how you really shouldn’t do this even though you both really want to

Fourth, I don’t want to go all The Rules on you, because, barf, but I want you to watch yourself for signs of becoming the World’s Most Accommodating Girlfriend Who Is Always Cool With Everything Because She Understands How Busy You Are, Dear. Keep your own needs in sight, ok? Put yourself out there, but watch for reciprocity. Let him do his share of planning the time you spend together and looking for ways to delight you and improve your life. The sad truth that we’ve discussed here before is that you can adore and have massive pantsfeelings and chemistry with someone who isn’t a good partner for you. It can also be easy to get sucked into the idea of The Future, Where Everything Will Be a Little Bit Better Than It Is Now, If You Just Believe Hard Enough. Love is risk. Love is optimism and hoping that you’ll beat the odds. But brand new love should be awesome all the time Right Fucking Now.

Right Fucking Now, I’m all the way in love. And one way I know that (as your fellow anxiety-monkey) is that my biggest anxiety these whole past few months has been “This is so fucking great. Is it TOO good? Should I be having more anxiety about it?” And the answer every time has been um, no, because it’s GREAT and he is GREAT, idiot. I didn’t make pro and con lists* about whether I should date him or love him or whether it was the right time or check in with my friends to see if it was a good idea…I mostly checked in with my friends to say “GREAT DUDE IS GREAT, YOU GUYS, LET ME TELL YOU MORE STORIES ABOUT THAT.” I didn’t worry about how it will all work out (except to occasionally worry that I wasn’t worried enough), and something magic happened to my jerkbrain: It shut the fuck up for a while and decided to let me be happy.

So the last thing I’ll say, as your adopted love-guide, is to suggest if you decide to go for this thing is to have all the sex, eat all the breakfast, and to let yourself enjoy it fully. But also, since you are not quite trusting yourself or him, put a date a few months out on your calendar where you sit down with a journal and write truthfully about how things are going. If that journal entry  looks AT ALL like a list of pros and cons about whether you should be dating him at all, if you find the worries and circular reasoning that you’re having now at all reflected there, if there are some consistent ways that your needs aren’t being met, then see it for what it is: You risked, you tried, and now you have some more information about whether this will make you happy in the long run. That’s a smart as you can be about things, I think, and still maybe let yourself maybe be happy.

*Blanket Statement: If you find yourself making “pro” and “con” lists in your diary about whether you should be or get involved with someone, you already have your answer** about how this is going to work out.

**Hint: The answer is CON.

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42 comments
  1. Beautiful.

    I’d add: as much as people deserve second chances at life and happiness in general, they do not deserve a second chance with you. Nor a first chance either. Nobody deserves anybody, ever. So cross that one off the Pro list.

    • JenniferP said:

      TRUTH: Second chances, like all chances, are solely at your discretion and not deserved by or owed to anyone.

    • Sheelzebub said:

      This. ELEVENTY.

  2. MHM said:

    This sounds exciting, but there are some flags here and you are smart and well aware of them all. This guy has had two marriages by age 40s. And he is only 4 months broken up and getting involved with someone. He has children to support and (again) he is already getting involved with someone. He has disappeared on you- there were reasons, but you have felt hurt after involvement with him in the past as he had not told you his real situation (to me the biggest flag, including the fact that you have excused him for this- is an apology enough?). These are interesting facts. Before jumping right in, maybe it would be good to get a sense of his life goals to see if you are heading in the same direction? Do you want kids, does he want more? Where does he see himself in 5 years? Are you looking to get married soon, and what does he think about marriage numero trois (if applicable)? Perhaps have yourselves a pre-pants talk with a skeptical mindset.

    Since he wants to be casual now, you don’t have to date him exclusively. Seeing other guys may help you have more perspective on this guy’s situation. Instead of worrying about him, as I see in your letter (Do I disapper so HE can see other people), I agree with asking: Does he meet MY needs. It is another flag that you are so worried about taking care of him? Is this your usual style or does he pull for this somehow?

    If it’s meant to be, you will surely feeling more at peace with the whole thing as time passes. I agree with everything the Captain said! If you are constantly evaluating this, bad. If you are just happy and not worried about stuff, yay.

    In sum: Skepticism! Slow it down! Other suitors are okay! Evaluate and reassess!

  3. Yan said:

    Awesome advice. Because it needs to be about You and managing your own feelings and needs and wants, not someone else’s.

    The way I see it, everyone has baggage, and the older you are, the more there likely is. So baggage? Not really a cause for concern, necessarily. But if you’re not raring to go, to jump past barriers and see what happens right at the outset, so giddy happy to be WITH someone that you don’t mind the luggage in the foyer? If the issues are so big that you’re trying to rationalize it before it even starts, consider whether you really want it to start.

    • Yup, we all have baggage and we keep picking up more as we get older. In fact, I’d be more skeptical of someone who made it into his 40s without a single suitcase. From my experience, it’s not the specifics that matter (exes, kids, joint custody of the family dog, etc) but how the person deals with their isht. By way of example: two and a half years ago I went on an awesome first date – massive pants feelings, easy conversation, lots of laughter, mutual eagerness to set a second date. And on that second date he said “it’s important for you to know that I’m currently unemployed and I’m still living with my ex.” He was open and honest about it, I asked a lot of questions, and then remained observant on our next few dates to make sure that the things he said were carried out in his actions. But that wasn’t the main dynamic of our interactions — mostly it was hot pants and excitement to introduce each other to our friends and long conversations about our pasts and our future. I never once thought “is he ready to date me,” but I certainly did ask myself if I was getting what I needed, wanted, and deserved from our relationship. The answer was always yes, yes, and yes, and y’know what? We got married on Friday! And the Captain was there!

      • Yes! With my honey, before there was dating there were Many Long Phone Conversations, one of which was “My divorce was just final but my ex is pregnant and I am living in her house taking care of our other two kids because she’s on bed rest.”

        Which, you know, sirens and alarms, but I later moved to Texas and married him anyway, and even though I hate Texas, I love him and those three giant children very much.

        • Bunny said:

          Yes! With me it was my partner telling me \”I am currently homeless, not a student at this university like you, I just gatecrashed the party and thought you looked fun and would like to get to know you better, in whatever context you\’d like.\”.

          We\’re celebrating our 10th anniversary-of-sexing this year, live together, have two cats and are blissfully happy. I attribute our success mostly to the fact that being honest with each other about our circumstances, goals and needs, and updating each other on those as they changed, and always being willing and prepared to deal with those things conflicting with each other. His baggage might have been a deal-breaker for a lot of people, but knowing the truth about it and talking about our mutual goals from the beginning, and then regularly since then, has helped a lot. It\’s never stopped being fun.

  4. Sheelzebub said:

    What the Captain said, though I’m on Team Jettison This Dude Straightaway.

    LW, you’re so worried about this guy and his needs that you’re ignoring your own. He isn’t entitled to a second chance from you. (In fact, if he wasn’t honest about his marital situation when you first met him, the only thing he has the right to expect from you is mirthless laughter and a middle finger–anything nicer than that should inspire him to get on his hands and knees and kiss your feet.) He’s four months separated (for the second time) from his second wife and he’s already starting something with you. That is indicative of a pattern on his part. And you’re kind of being his caretaker in trying to figure out what he *really* wants/needs and what would be best for him, and he’s putting the responsibility on your for his decisions (“you make it hard for me to date other people” etc.) instead of being a damn grown up and owning his life.

    I’d advise against even seeing this guy even casually, seriously, or as friends. There’s too much history and wishful thinking around him, and it will be easy to get sucked in. There are plenty of cool people you can meet who will not deliver a thousand boxes of angst and dramz pizzas to you.

    • Emmanonymous said:

      And unless I misread the original letter, he’s still not actually DIVORCED yet, just separated.

      I think it probably wouldn’t hurt to wait until the judge has signed off on the final papers. If he’s a good guy, he should hopefully understand that you want it all legally squared away, especially given that he’s gone back to his wife once before. That also helps address your concern about rebound relationships, and has the bonus factor that it keeps you away from any possible involvement in his divorce.

      I can tell you for a stone fact that his lawyer will have told him that he needs to NOT DATE ANYONE while the divorce is being processed. He’s technically still married right now, and if you date him, you’re handing his ex a way to make this divorce uglier. If you two start dating, she can raise the specter of adultery as blackmail to get the custody agreement or spousal support or division of property that she wants.

      Divorces generally don’t take longer than a couple months to work out when both parties are basically in agreement (and if it’s messy, you should think double-hard about staying out of it!). If he’s really interested in you, he’ll still be interested in you in eight weeks. Conversely, if he’s looking for a fast rebound relationship, or doesn’t have his marital stuff thoroughly sorted, that too will be obvious in a short period of time.

      I think you ought to hold off on this until ALL the paperwork has been filed, at the very least, and preferably until the post-paperwork waiting period is elapsed or nearly so. If he’s already started the lawyer work, he ought to be able to give you an idea of where he is in the process and the date on which he expects to be officially divorced.

      • JenniferP said:

        Good catch!

      • sasha said:

        One caveat here: the time it takes to get a divorce varies a lot between states. Down here in the Deep South, you have to wait 6 months before you can even file the paperwork, and that countdown clock doesn’t start until you live apart. So between the time it takes for one (or both) partner(s) to find a new place to live, move, go through the waiting period, file the paperwork, and go through the legal system, even the “cleanest” divorce can take upwards of a year.

        I know this because I started dating my most recent partner shortly after his separation and before his divorce was completed. In their case, the divorce took 9 months, even though it was fully mutual, she moved out within 2 weeks, they divided up all the property themselves, had no children, and neither claimed alimony or protested in any way. We kept our relationship under the radar for this time period – I told a couple of my closest friends, and he told one or two of his closest friends, but we didn’t make it public until after the divorce was finalized. Which, while necessary, was awkward – I didn’t really like hiding it.

        I went through a lot of the concerns LW has, about his wanting/needing to date other people (he’d been with his ex for over 10 years, since college), about whether he was “ready.” We had lots of conversations about it, but I came to realize that it was up to him to decide whether or not he was ready or not; I didn’t need to make that decision for him. We took it REALLY slow at first and kept things very casual. Which mostly worked, as I also had just been through a big breakup and wasn’t sure I wanted a serious relationship, either. Though I’ll cop to trying too hard to be the World’s Most Accommodating Girlfriend Who Is Always Cool With Everything Because She Understands How Busy You Are, Dear.

        It worked for a while, though in the end it turned out that his baggage was such that it made meeting my needs impossible. But that was bound to happen even if I played by The Rules and waited x months before dating him.

        So, LW, if the timing is all that worries you, I’d say go for it. But if you think the timing is really just a cover for other, deeper concerns you have about him and how he’s treated you, then I’d take some time to figure out what those concerns are. Good luck!

        • Emmanonymous said:

          I’m in the Deep South too (Mississippi, specifically), and the process took me less than 90 days. Obviously, states vary, and your point is well-taken.

          Still, I think it’s a good idea that a potential romantic partner be well into the process of actually ending the marriage. Separation is a step in that direction, but people get back together after separation all the time. The LW’s specific person-of-interest has in fact done that once already, so a little extra caution seems reasonable to me.

          If I were considering dating this guy, I’d want to know that he is really and truly done enough with his marriage, enough to commit to some paperwork and take positive steps. I’d also want to know that he isn’t dipping his toe into the dating waters while letting the ex think a reconciliation might be in the cards. (And, of course, that he is actually separated, not just cheating!)

  5. Britt said:

    Brilliant advice as usual, Cap. 😀

    LW, I want to highlight one particular bit: The sad truth that we’ve discussed here before is that you can adore and have massive pantsfeelings and chemistry with someone who isn’t a good partner for you.

    This is the very crux of what you have to figure out, I think. Not just do you like this person, do you have happy pantsfeelings for him, do you want to bone him and enjoy some delicious french toast, but can he be the partner you need him to be right now. Not a week or a month or a year from now, but right now. You don’t need to save him from himself and walk away so that he can’t do something he’ll regret, but you may need to walk away for yourself if you don’t think that you two can have the kind of relationship that will make you happy and meet your needs.

    It’s really sucky, for lack of a more elegant way to say it, but sometimes we’ll encounter people that are so great and we feel all sorts of lovely butterflies and our pants have happy feelings, but we’re forced (either sooner or later, but always eventually) to acknowledge that they’re not the right person to be our partner, for any number of reasons. Shoot, I have a number of male friends that I would have GLADLY dated, were it not for the fact that for some reason they are amazing friends but terrible boyfriends.

    I’m not saying that’s the case with your man-friend, LW, but I did want to absolve you of feeling like you’re making some judgement on him as a person if you DO decide that going forward with a relationship is not the right decision. It doesn’t mean you’re saying he’s not good enough for you or anything, just that he’s not the right choice.

    In any event, good luck and Jedi hugs!

  6. theLaplaceDemon said:

    “*Blanket Statement: If you find yourself making “pro” and “con” lists in your diary about whether you should be or get involved with someone, you already have your answer** about how this is going to work out.”

    That x 100.

    Also, suggestion: Forget the pros and cons list, and instead make a list of what you needs are. Be brutally honest with yourself. Put it aside and come back to it in a view months and reevaluate your current situation.

    I suggest this because when I date someone Darth-y I tend to magically readjust my view of what my needs are to accommodate said Darth. And in a way where it’s really hard to see clearly and remember what Good and Healthy looks like – like, I forget that things like “using me as combo MomTherapistSexmachine” was theoretically a dealbreaker a few months earlier. Writing down my needs when I’m NOT in that defending-Darth stage is a way I protect and check myself, because when I am deep in it with Darth it’s much harder to be honest with myself about my needs.

    (disclaimer: obviously, what your needs are can change–I still think it’s useful to sit down with yourself and spend some time thinking about whether your needs have actually changed or if you’re just accommodating Darth).

    Also – I hesitate to make this into a generalization, because my sample size is not that large and is certainly not randomized – but I have never had good luck with someone who says things like “let’s just see what happens” or “let’s just not put a label* on it” once Mutual Attraction has been established. At least in my personal dating history “let’s just see where this goes” means it is not going somewhere good.

    *MAJOR disclaimer: I totally respect rejecting romantic LABELS, but I’ve only had significant others/romantic interests use the phrase to actually mean that they reject the idea of articulating clear boundaries and expectations for the relationship, and not actually about rejecting he label–situations where “I don’t want to call you my (gender)friend because I’m scared of labels” really means “I don’t want to treat you with the same level of consideration I would treat a (gender)friend or be held accountable for my actions.”

    • JenniferP said:

      I love the idea of writing down needs and revisiting them frequently. In fact over the winter I did that and then adapted it into the “what I’m looking for” section of my dating profile.

    • Liennae said:

      So true about the label thing. I find it’s usually used by people who want to get in your pants so badly that they’ll fudge having feelings for you until they get bored. Labels tell you what to expect, and the message sent is generally “I don’t want you to have expectations of me.” Yes, some people/relationships defy labels, and don’t use them for a very good reason, but those relationships work best when based in a mutual decision making process that still defines clear boundaries and level of commitment.

      • JenniferP said:

        Oooh, good observation. Bonus points if they preemptively say “Let’s not put a label on this right now, baby” before it’s even occurred to you to put any kind of label on it. That pretty much translates as “Let me put it in you later! But don’t expect me to call you afterwards, and I will be a giant weirdbag if you call me.

        • Liennae said:

          Oh the things I wish I knew in my early 20s. I can’t help but look back on them and cringe.

    • maggie said:

      I didn’t even meet one dude from OKCupid, once, because I mentioned the word “date” in passing, and he got very huffy about me saying ~date~ because we’re just going to go ~hang out~ and see how things go and ~ladies~ always think ~WE’RE DATING~ after a date, etc…

      Red flaaaaaaaagged! No thanks! I’ll stay home..!

  7. xenu01 said:

    I just want to add this: the guy doesn’t have to be a Darth for it to not work. I mean, the Captain and others have stated this many times before, but explicitly, sometimes there are people who are wonderful in every way and the relationship seems to be perfect- except that you are not the real, happy genuine person you are in that relationship, and so everything feels slightly cock-eyed. I had a relationship like this and it ended very badly; the truth of the matter was that no matter how great we were in every day life, we literally brought out the worst in each other.

    • jfs said:

      Oh, this.

      I was at my best friend’s birthday party at the weekend. She and I have known each other for 20 years. I love her, I love her husband. I was best man at their wedding.

      The only time we’ve not got on was when we dated. We argued, we fought, we made each other so unhappy. Now that we’re friends, the pressures are different, and these are ones that we can deal with, and which make us stronger together, not weaker.

      • xenu01 said:

        I am friends with the person I mentioned above, too! Took a while, and we’re more meet-up-for-a-beer-when-I’m-in-town friends, but friends. The qualities that we have that made us incompatible as loouuuuverrrrs make us perfectly suited as friends. Funny how things work out, right?

    • JenniferP said:

      Truth! :looks at last two serious ex-boyfriends, who are dear friends:

      The reason I was poking around in it so much for Vader tendencies was that I didn’t know the source of the LW’s anxiety – was it the guy’s history itself or were there certain behaviors that were setting off her alarm bells.

      • xenu01 said:

        Oh, I know, and I think your advice was excellent! It’s just that sometimes even when we date Darths, we don’t see that at the time because we are so busy defending them all the time in our heads. And sometimes you just make each other unhappy and no one’s a Darth- and sometimes you ARE dating a Darth and can’t see it until five years later when you’re having drinks with your best friend and you can laugh about it.

    • Man, I don’t know if I’ve EVER had a relationship where I can feel like I’m the real, happy genuine person I am. Which is why I’m taking an extended break from relationships, because I have no idea how to do that.

      • At first I thought you wrote “happy penguin”. That would be a good description too 🙂 Good luck!

    • Elysia said:

      I mean, the Captain and others have stated this many times before, but explicitly, sometimes there are people who are wonderful in every way and the relationship seems to be perfect- except that you are not the real, happy genuine person you are in that relationship, and so everything feels slightly cock-eyed.

      Sometimes they’re just the wrong pants! 😉

  8. LW said:

    LW here. Thanks for the thoughts and I am definitely drinking it all in. Remember? Major overthinker here. In all fairness he was totally upfront that he was separated last time but was not yet divorced. We clicked majorly and I assumed he was farther along in the process than he was.

    As for the ‘caretaker’ aspect? I’m just trying to protect myself, if that makes sense. I’d rather he date oodles of people now before I decide to get involved. I think I am trying to create enough ‘outs’ this early in so that if he decides he’s in, he’s all in, like I would want to be. I’d like to proceed with this and see what happens but I’m scared of getting burnt again (not specifically by him but just, you know, relationships in general. I know, I know, that’s no way to date.) That’s why I gave him the ‘homework assignment’ of figuring out what the hell it is that he wants (in general and from me) to make sure we’re on the same page. I selfishly want him to be in a good place so that ‘we’ are a real possibility. I’m not interested in being one of the many or having him realize a few months in that he wishes he had been single dude for awhile. Timing is everything and it would suck to have it be wrong twice.

    MHM – Sadly being single and dating in one’s thirties in the middle farmland states means that numerous kids and ex-wives are the rule, not the exception. I am the abnormal one, thank goodness! And no worries, I am dating abundantly at the moment 😉 And plan to continue doing so until there is some sort of real commitment/involvement on both of our ends. Although, I always feel a little ‘cart before the horse’ when I start talking major life issues (kids! marriage! religion and politics!) with someone before we decide if we like each other and can get along for an extended car trip or the equivalent. Anyone have advice or perspective on this? Especially with the internet dating, how soon and how much is too soon/much? I am of the school of thought, better to scare them off early (guess who doesn’t want kids? and who knew it would cool off most suitors?) and weed out the real potentials.

    LaplaceDemon – That is a fantastic idea and one I am going to get on immediately, if not sooner. I genuinely like being around this guy and like who I am around him but I need to know that he is interested in being what I need too. Le sigh!

    Thanks again for the insights. Jedi hugs to all.

    • Heather said:

      Hi LW, just wondering how this comment “guess who doesn’t want kids?” factors in the balance of his having kids and you considering a serious commitment with him?

      • LW said:

        oh, i am totally cool with HIS having kids…and my being involved with them. he’s an excellent father and they seem like great well-adjusted kids. i personally don’t want to spawn in the future. which generally scares the bejeebers out of potential romantic interests.

    • MHM said:

      Hi LW!

      I totally see what you mean about dating in farmland.

      What I found helpful in my single 30s- date guys in their 20s. I did marry a guy 3.5 years younger than me and one of my best friends married a guy 7 years her junior! I was in the city though. Anyway, you sound very normal to me.

      But I digress, I am just like you- I put it all out there and let the chips fall where they may. I did not work hard at impression management and I let the guys self-select out. If I got super worried about what the guy thought, this was usually a huge red flag telling me: you feel anxious around this guy! I think it’s best to have major issues on the table in the first 3 dates. If there are deal breakers why not know of them before you get too involved (cuz then it’s hard to break up!).

    • Vicki said:

      For what it’s worth, I’d make more of a point of bringing things up if you are (locally or otherwise) in a minority. So, not wanting kids when most of the men you meet want kids is worth mentioning early; if you want a church wedding, and most of the potential dates you meet are also Christian, it’s less likely to be a huge issue. (For minor things, how common it is matters less: few people will decide whether to date you based on how you feel about peanut butter and jelly sandwiches.)

  9. Lieutenant Right said:

    Captain Awkward’s advice is spot-on, of course.

    However, I just want to say: Don’t look for red flags to determine if the relationship will end. Of course the relationship will end! All relationships end, in divorce, break-up, or death. A relationship ending is not a failure, it’s just how the relationship ended.

    One thing I noticed is that you never talk about the man’s personality having defects. When Captain Awkward says look for reciprocity, she doesn’t mean that “he has to pick up his kids to take them to a soccer practice and has to cancel our date last minute” is a failure of that. She means, “he accuses me of taking up time with his kids” or “he doesn’t get back to me about making plans and when we finally do he has to break them.” The former indicates problems with time. The latter two — a) DARTH VADER ABORT ABORT and b) unneeded stress and frustration in your life!

    The problem is, if you just walk away without trying, how will you KNOW if it’s not going to work? All the suggestions Captain Awkward has given point to the fact that you have to dip your toe in the waters to get a better idea of what you’re getting into. Go on a couple dates. Get into relationship mode. Is it satisfying? Hooray! If it isn’t, you have your answer. And remember to use your words! If he keeps having to take his kids to soccer practice on date night, ask if you can have a different date night. If he refuses, you have your answer.

    • JenniferP said:

      All relationships end = word. You can get paralyzed trying to control the outcomes instead of enjoying (or evaluating) the present and whether it’s working.

  10. ahn said:

    This letter resonated with me because I’m in a similar situation. Started a relationship with a guy who had just been through some major life changes (divorce, re-evaluating how to live his life) and wasn’t expecting to find someone he clicked with in a serious way so soon. But since the clicking was pretty damn serious, we went with it. And it kind of ran away from us and became something very partnered and serious very quickly and then he realized that he really did need some time before he could once again be in that type of close and committed relationship with someone. The intentions from the start were good, like it sounds like your guy’s are. But sometimes, when in the midst of change and growth and life stuff, it’s hard for someone to know exactly what they’re going to need. I don’t think you’re wrong to wonder if he might need some time to just be on his own for a while/do a bunch of casual dating. He might not, and either way it’s not something you can be the babysitter of. He’s going to have to come to it on his own. I would advise trying to keep a light touch with the relationship, which it sounds from your follow-up comment like you’re doing. And keep advising him to get in touch with what he really wants and needs. You can’t know or own that, and I would caution strongly against becoming his confidant about such things, but the clearer he is about it with himself, the easier it will be for him to know what the relationship should look like. Change is so tricky and it can be impossible to see it clearly from the inside. I think if the relationship feels right you should go for it. But be prepared to be adaptable and, like the awesome commenters above said, be very very sure you are still having your needs met. If a strong connection is there it might be able to weather some shifts and changes as things get started.

    (My guy and I are working on figuring out how to scale back and renegotiate our relationship into something more casual and less partnered. It kind of sucks a whole lot but since “serious partnered relationship” isn’t one of my needs right now I’m willing to work with it, plus I’m sorting through a whole bunch of my own change-related issues that I’d put on my own back burner during all the intense relationship stuff. It’s tricky but possible and I don’t at all regret the fact that we did sort of rush into things and then needed to back off. I would have more regretted not going for it at all.)

    • LW said:

      ahn – i’m sorry to hear about the circumstances that brought about a relationship reevaluation but glad to hear you’re working it out. you’ve kind of summed up and offered a look at one of the potential futures. it’s nice to know that it can be navigated without hardcore absolutes. it’s sometimes hard (for me) to sit back and have a light touch sort of relationship but i am working on it…that may be one of the things i need to evaluate. best of luck with your life changes and big hugs.

      • ahn said:

        thanks and big hugs back! One of the things I’m learning is that hardcore absolutes in relationships are pretty impossible. People change and I’d rather allow for change in both myself and the person I’m with than try to make the relationship work in some set and determined way without taking the change into account. But it’s HARD and takes a lot of communication and honesty. The light touch thing is really hard also, for me, and one of the things I’m glad to be learning how to do. But yeah, as long as needs are being met (and I did some hard thinking about whether or not “serious committed relationship” was one of my actual right-now needs or a fantasy wish-it-could-be need), there are lots of ways to make things work. And change keeps happening and one day things might evolve again with myself and this guy, or “serious committed relationship” might move out of fantasy-need and into actual-need, and then I’ll need to re-evaluate. But we can only work with the pieces we have right now, as much as I’ve often wished all the over-thinking I’m prone to do could make it different somehow. 😉

  11. Wiley said:

    I need to tattoo this entire column to my forehead.

  12. Mercutia said:

    It’s an uncharitable thought, but I’ve done enough dating-in-my-30s to have seen it more than once: Some people are crap at being alone and when one relationship ends they look immediately for another one with a benevolent girlfriend-mommy who will pet their hair and tell them they are smart and pretty.

    Oh, this.

  13. Adelene said:

    Here’s what I’m seeing: It may or may not be possible to have the relationship you actually want with this guy. Even if it is, theoretically, possible, you’re not there now and there’s no obvious way to get there. So if it is possible – which you really don’t have any way of knowing ahead of time – it’s going to take a *ton* of work to get there.

    You aren’t obligated to do that work. Really.

    It seems like the kind of thing that a person *should* do, and our society is full of stories about how people don’t even hesitate when they’re presented with that kind of choice, but those are stories, and this is your life. It’s okay to take the easy option. Especially since – this being real life and not a romance novel – there are plenty of guys out there who are just as awesome and don’t require a herculean effort to make things work.

  14. Araine said:

    I just wanted to say thank you for that piece of advice at the end of the letter.

    I’m not in an analogous situation, but I am at the end of a pretty great relationship with a great guy who I am just not working out with, and I’ve felt horridly guilty about the oncoming breakup for the past month and trying to convince myself that it will all work out.

    I actually wrote a pros-and-cons list over whether or not I should break up with him last week (it is sitting on my nightstand), and your blanket statement gave me the kick in the pants to actually go through with the breaking up and we have a Skype call planned for tomorrow and I am really nervous but also I honestly feel like it is the right and best thing to do.

    So, thank you for helping me to clear it all up.

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