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cheating

Hello!

I’m sorry, this is complicated. I am in my late thirties and have fallen in love for the first time in my life. We have been in love for a year. I believe he is the love of my life, which I have never believed about anybody, and he believes that I am his. He still lives with his ex-wife and their three children. This made me hesitant at first, but we have been so open, honest and intimate that I trust him.

His ex-wife suffers from depression which renders her unable to work, unable to care for the children, and unable to take care of household tasks. They have been living together, divorced, with him taking care of her and the children for several years. He does not like this, but believes it is best for the children. I am happy to live separately and I don’t want kids of my own, and I trust him, so I am fine with that situation.

However, his ex-wife is hoping that he will eventually come back to her. When we fell in love, he asked me to keep our relationship secret for a while, wanting to wait for when she was on an uptick so that he could break the news to her that he is seeing someone. He is also wary because one of the kids has explicitly said that he does not want his parents to date anyone else (although he hasn’t said that in the past year). So I agreed to keep us secret until the right time.

The other day, he came to me absolutely shaking, like he had just walked away from a plane crash or something. He told me that he tried to take up with his ex that he would like to start dating other people. His ex had a complete breakdown and told him that if he dates anyone else, she will move out and have the kids every other week. He couldn’t let that happen, partly because he can’t bear to be without his kids so often and partly because she won’t care for them when it is her turn. He was also panicking too much from her breakdown. So he promised her that he would not date anybody else.

Now he is asking me to keep our relationship secret for 10ish years, until the kids are grown. He feels extremely guilty for asking me this, and says he understands perfectly if I don’t agree to it, but he seems to think it’s the best option for the situation. I don’t think it’s good for the kids for a parent to keep such a huge secret from them, but that’s not my call to make. I also think this is preventing his ex from moving on with her life and her love life, but that’s also not my call to make. Having a secret relationship for 10ish years sounds horrible for both of us, and of course there is the risk we will be caught. I think his solution is terrible, but I don’t have a better suggestion. Does anyone have a better idea?

Sincerely,
A person with a she pronoun

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Hello friends! It’s that time, where we answer the things people typed into search engines as if they were questions. It’s a good way to check in with people’s preoccupations on a large, anonymous scale and it’s usually pretty fun.

First, as is traditional, a song:

(Lyrics at the YouTube link)

Also I know I used this one last year, but it came up when I was looking and I love it so:

Ok! We’ve got witchy autumn-themed music cued up, so without further ado:

1 “How to know if a girl wants to hang out?”

Say the words “would you like hang out with me” & include a specific place, day, and time in your invitation. If she says no & does not suggest an alternative time/day/venue, like, “Can’t make that, but I’d love to get together – can we do x instead?” and never follows up with her own invitation, she does not!

2 “What to do when your friends tell you to date someone you dislike and they dislike your crush.”

For the first person (the one you dislike): “If you like him so much, you date them.” 

For the second person (the one they dislike): “You don’t have to date them!” 

3 “What does it mean if my brother in law keeps saying flirty comments and trying to touch me in front of his brother which is my boyfriend?”

It means your brother-in-law is a creep & a sexual predator who is trying to groom you to put up with this. It’s okay to yell “gross, don’t touch me!” or “ew, why would you say that!” or “Nope!” and leave the place where he is and also avoid him forever, like, “Nope, I don’t want to hang out with your creepy brother, hard pass.” Like, you can make a giant stink and insist that this never happen again. Also, I DEEPLY question why your boyfriend doesn’t step in or stick up for you since this happens in front of him. Have you discussed it with him? Because it might be time to avoid the whole creepazoid family.

4 “How to send an email asking if anyone has dietary restrictions?”

In your email about the gathering/event, say “Please let me know if you have any dietary restrictions or food allergies I should know about!” 

I also like it when invitations say “The tentative menu is x, y, and z – please let me know if you have any dietary restrictions or food allergies I should know about!” 

People who have dietary restrictions are pretty used to this and will have no problem responding.

5 “He criticizes my clothes.”

Is he the boss of you or your closet? Criticize his fallacy that you care about his opinion about that.

6 “Reaching out to an ex boyfriend after many years.”

Why? Self-awareness about why you’re reaching out and low expectations for what you’ll find when you do will make this much easier than it might otherwise be.

7 “How do I know my best friend is not cheating on me?” 

Is your best friend not allowed to have other friends?

I saw this and then….whooo boy: 7a “My friend is overly possessive of me and wont even acknowledge anyone else as my friend.”

Friendship is not a pie. You’re allowed to have multiple friends, people who try to isolate you from others do not have your best interest at heart, and if this friend won’t honor that you’ll need to end that friendship.

8 “My boyfriend wont let me eat.”

Yeah, that’s a “get yourself safe & away from him” situation. You’re the boss of your own food. Please keep yourself safe.

9 “What to do when your boyfriend doesn’t shower.”

If your partner’s hygiene grosses you out, it’s okay to be very blunt, like, “I notice you don’t shower, what’s going on with that? Please take a shower when you know we’re going to see each other.” “I don’t want to have sex/be close to you when you haven’t showered, please take care of it.” 

10 “How do you tell your spouse of 50 years that they need to shower better.”

“Babe, I need you to be more thorough when you shower – you’re missing some spots.” 

You may have to get realllllllllly specific about which spots. In 50 years you’ve had to have survived some awkward conversations, what’s one more?

11 “Why does my daughter continue to pick undesirable men?”

I don’t know! Assume she’s getting something out of the relationship that you can’t see, assume she has different priorities from you about what desirable even is. Then, remind her that you love her, try to keep an open mind, emphasize her choice & her agency in her romantic decisions, keep lines of communication open, try to hang out with just your daughter sometimes (vs. having both of them at everything). If the dude is actually awful, this will help her find her way back to you. If he’s a decent person but just not who you would choose, this will help you keep a good relationship with your daughter while you give him a chance to change your mind or everyone waits out the inevitable breakup.

12 “My children want to live with my rich in-laws instead of me.”

There is clearly waaaaaaaaaay more story here.

13 “Guy said maybe in the future meaning.”

Not now, i.e., don’t make any life plans around this guy.

14 “When relative distances from you do you try to contact or leave alone.”

If I know the source of the conflict or if things seem really out of the blue, I might try one time to address it – “Everything ok?”

But also, in families, not everyone has to like everyone, sometimes we get along better with some breathing room & space. Am I sure that the distance is about me, specifically (and not something stressful in their lives they’re dealing with) & does it all need to be resolved right now or can I trust that a little time will work it out?

15 “My boyfriend won’t watch a show with me.”

Not everyone has to like or watch the same entertainments. Let it gooooooooooooo.

16 “Doesn’t want me to meet his friends to take it slow.”

Hrm….

“Taking it slow” can be a good/healthy/reasonable thing.

Wanting to hold off on introducing someone new to your friends because you’re not sure yourself whether this one is a keeper can be a good/healthy/reasonable thing.

If someone you’re dating says “Let’s take this slow!” aka “I really like you but I’m not fully-committed yet and I’m taking my time before I decide that (& so should you!)” then it’s a signal to adjust your expectations accordingly, like, slow down your own commitment/investment level, slow down introducing him to your friends & family, slow down on future talk, remind yourself to put some time & love into the other people in your life & not disappear into New Couple! mode, & maybe don’t delete that dating profile just yet. Also, let the person who said they wanted to take it slow do more of the work of staying in touch, planning dates, etc. Like maybe it’s a prelude to a rejection, or maybe it’s an opportunity to give yourself permission not to do much or any work around this person right now. They’re taking it slow! No worries, you’re busy with your own thing and will check in when you have some time!

Also trust your instincts and trust what you want! If you feel like you’re being hidden away & compartmentalized from your person’s actual life, or he’s all “take it slow” about meeting friends but really clear about wanting all your time/fidelity/attention/commitment, if something feels unbalanced or unreciprocated, maybe trust that itchy feeling that made you Google this and pull back entirely. People can fall in love at different speeds, people can also string you along because they like your attention and they’re incapable of managing the whole “when I said I was single I meant I was separated and by separated I mean I’m still very much married and I promise I’ll tell her soon and anyway that’s why nobody can know about you, but we’re still having sex tonight, right?” discussion and order of operations like an ethical & trustworthy adult.

17 “Don’t want to spend Christmas with disabled step daughter.”

Listen, your holiday plans are your own – spend them how you want. Also, this phrasing does not make you sound awesome, so, probably it will be a huge relief to your stepdaughter if you just go on a cruise somewhere with her parent/your spouse or better yet with your family of origin or some good friends!

18 “I ghosted someone and now he’s sending letters to my house.”

Yeah, that’s creepy. Safety experts advise communicating directly with the person one time to say “I’m not interested, please stop contacting me,” using a medium where you can document that you said this (text, email), to remove plausible deniability from the situation. Then, never respond to any communication again, the logic being that if someone sends you 100 letters and you respond to say “I told you not to send me any more letters!” you’ve taught them that it takes 100 letters to get your attention so next time they’ll send 101. Every time you engage with the person after you tell them to stop, even if it’s yelling at them to leave you alone, it’s like buying yourself a few more weeks of stalking behavior because they are getting that little jolt of attention they wanted. The hope is that if you starve them of all attention & feedback they’ll lose interest.

Additionally: Tell other people in your life what’s happening and ask them (esp. any mutual friends) not to engage with the dude or give him any information about you, tighten up your social media visibility (block him everywhere if you haven’t yet, be mindful of sharing location data & photos online, he’s almost certainly monitoring whatever he can find), check on your locks/make sure you close your windows when you go to bed or leave the house, save all the letters in case you need to show them to law enforcement, vary up your routine & commute.

19 “How do you get your neighbor to quit asking for stuff.”

Say “no” every time they do ask, be very selective about when or if you answer the door, even make it clear – “I can’t/won’t help you with that, please stop asking.” 

20 “What to do when your new boyfriend is a slob.”

People change slow if they change at all, and you can’t make them do it.

Use that information how you will. Either find someone who is more compatible with you around cleanliness & hygiene stuff, choose your battles & speak up about the stuff that affects you, at risk of him not taking care of whatever it is and outright deciding “hey, I don’t wanna change the sheets more and I don’t wanna be criticized about it, I’m out!,” decide that you will probably never share a household and that’s okay, or learn to love the mess. He is a new boyfriend and you have the choice to be like, whoa, you have the best smile and we like all the same books, but I don’t think this is for me.

21 “I can’t stop cheating on my boyfriend.”

You actually can, so let’s rephrase this: “Something about my relationship with my boyfriend is not working for me and I am unhappy with him, so I keep cheating on him instead of breaking up or talking whatever it is over, but I’m also afraid of losing him or hurting him so I keep delaying the inevitable.” 

Feelings happen and they don’t always happen at convenient times or in the right order.

Let’s take feelings out of it for a second and talk about safety. If you’re sexually active, if you agree to have a monogamous relationship with someone and they trust you to hold to that agreement, and you’re also secretly having sex with other people, you are messing with consent. You are not allowing your partner to make informed decisions about their own sexual health and risk tolerance. That is a really shitty, violating, possible health-destroying thing to do to someone and it’s in your power to not do that anymore.

22 “When mothers barge in son’s room to find him wanking.”

Look, I know this is most likely a random porn search, but I grew up with a family who were pretty terrible about closed doors and privacy, so let me take this opportunity to say:

  1. KNOCK.
  2. WAIT FOR AN AFFIRMATIVE ANSWER BEFORE YOU TOUCH THE DOOR AGAIN.

Kids are people, people need privacy and respect, if it’s not a life or death situation (like someone is not literally bleeding, exploding, flooding, or on fire) you can fucking well knock and wait 30 seconds for everyone to get their britches reaffixed. You want little kids to learn to knock & wait for an answer before they interrupt you, you want your older kids to have respect and privacy and feel safe where they live, so, be the change (and the knocking) that you want to see in the world.

23 “Captain awkward cries all the time”

I cry a normal amount of crying + 20% if it’s a sad movie or if unlikely animal friends are involved somewhere or if it’s the part of the book where little girls send letters to their heroine about how they want to be astronauts someday. I also cry if someone is mean to me or someone I care about, if someone is unexpectedly nice to me, and….[censored for politics].

24 “Feel guilt quitting job manager asking me to come back.”

Good news, you don’t have to go back.

You can say “Oh manager, it’s so great to know you value my work, but this is the right decision for me. Thanks for asking, but no thanks!” 

And like, it’s good to keep things cordial with former workplaces if you can, but once you stop working there you do not have to respond to every communication you get. Once the question’s been asked and answered, you can ignore future requests.

And hey, if you decide you want to go back, this seems like a great time to ask for wayyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyy more money than you were making before!

25 “Husband supporting his adult children behind my back.”

Assuming “support” = financial support, yikes. Married couples need transparency & honesty about financial stuff. Maybe this is one for couple’s counseling and/or talking with a financial advisor to make sure that your shared savings & financial priorities aren’t being neglected and to dig into why he didn’t feel like he could tell you. Ya’ll need to open all the books and spreadsheets and accounts and air everything out, down to the penny.

One way to possibly handle this (after a full accounting/disclosure and some deep discussions) is to make an agreement going forward that X amount of money (the majority) goes toward your shared financial priorities & living expenses and Y (much smaller amount) of money gets split equally between each spouse to be spent/saved/invested as they wish without consulting the other, so if he wants to throw his monthly Y budget to his adult kids that’s up to him, you can still be confident that your savings & expenses are being handled and also have your own discretionary funds. It doesn’t remove the problem completely (I sense that the querent’s ideal amount of support for the adult children is zero dollars and no cents) but it does remove secrecy and lies.

 26 “Good headlines for dating profiles.”

  • “I’m shy and weird and nice.”
  • “Let’s eat cheese and do witchcraft.”
  • “Evil genius seeks henchmen for world domination scheme.”
  • “Winter is coming (Come hang out in my sweet blanket fort).”
  • “I just got divorced, everything sucks, wanna make out?”
  • “Let’s both put on a clean shirt and leave the house tonight.”
  • “Yes…and? Comedy/Improv dork seeks a willing player.”
  • “I promise I will never make you come to my improv shows.”
  • “My perfect date involves documentaries and crying.”
  • “Let’s canvass for the midterm elections and then fuck!”
  • “Severely allergic to cats, lilies, and people who ‘love to debate for fun.'”
  • “I like tacos, heist films, and books about space travel.”
  • “Let’s compare shoe collections (I wear a size 8).”
  • “Hold my hand during scary movies?”
  • “Weatherwax in the streets, Ogg in the sheets.”
  • “Ok basically my fantasy is to meet someone who wants to learn how to fence and then we’ll have duels and say witty, cutting remarks laced with sexual tension, who’s in?”
  • “My version of dating is to be really good friends who snuggle (a lot) and kiss (sometimes/a little) and do other sexy stuff (maybe/never). Who’s with me?”
  • “I express myself only in GIFs, memes, and rap battles.”

Be specific! To me, the secret isn’t to appeal blandly to the maximum number of possible people, the secret is to communicate your specific brand of weird in the hopes of attracting same. It’s okay to have fun with it, especially if the whole dating site seems like one big “I’m a chill relaxed normal person who likes to work hard & play hard, I have sanded off as many of my rough edges as I could before appearing on your app screen, I’ll break the news about the bagpipes and the family curse later, please swipe right!” avatar of the same person.

That’s all for this month. Live Chat/Short Answers return Friday 9/28 (I’m doing them 2x a month instead of every week, which I think I told Patreon but didn’t necessarily announce here), here is a kitten photo to tide you over:

fullsizeoutput_7eb.jpeg

Daniel Striped Tiger (L) and Henrietta Pussycat (R) are two soft brown tabby kittens who are best friends and excellent sleepy snuggle buddies.

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

Dear Captain Awkward,

A couple of months ago, one of my best friends (we’ll call her Beth) and her partner (we’ll call him Dylan) broke up. Beth and Dylan had been together for six years and living together for five. They seemed to have a pretty good relationship, although Dylan dominated the apartment with his belongings, said he couldn’t marry her until he was a “real adult” (at 34, while doing nothing to move toward his definition of “adulthood”), and was generally kind of moody. Beth did most of the adult work in the relationship, including keeping a job she didn’t love in order to support them financially and doing all the emotional labor because Dylan wouldn’t go to counseling, individual or couples’.

They broke up because Dylan deleted their anniversary on Facebook. When Beth asked him about it, he confessed that he had been secretly dating a coworker and no longer loved Beth. She was blindsided, not least because she was very good at checking in on the relationship and he had essentially gaslit her into believing that everything was fine for months. Dylan moved out of their apartment and Beth actually packed his boxes for him. I did everything I could to support her and tried very hard not to set Dylan’s things on fire and to discuss my deep contempt for him with mutual friends instead of with Beth. Eventually it came out that the coworker was married and she created a lot of drama and misery for Dylan, and I thought, Great! He’s getting his and I don’t have to do anything.

Unfortunately, now that his little fantasy didn’t work out, Dylan has decided that he DOES love Beth after all, and he is insinuating himself back into her life and her apartment. She told me yesterday that they were having sex, but that he “can’t make any promises right now” and he says, “We shouldn’t be doing this” (while still managing to fuck her), which is basically the sexiest thing someone can say. Beth, heartbroken and holding out hope that he’ll come back to her and they can make it work, isn’t doing anything that I haven’t done myself, but I am furious that Dylan is taking advantage of her feelings so he can have AND eat ALL THE CAKE. But of course when I tell Beth that, I become the Bad Guy. Captain Awkward, I don’t know how to support my friend while also making it clear that there’s no fucking way this guy is getting back in our good graces, especially not with this behavior.

Thank you for your time!

Hard-Hearted Harpy Wants Friend to Be Happy (she/her pronouns)

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Captain Awkward,

I’ve found myself in a really damn sticky situation. I’m polyamorous. I just recently told my partner, we’ve been together for 18 months this June, we’re engaged, and we have a kid together. (For anonymity, I’ll be referring to my partner as Darin and our son as Ash.) I love Darin, and I love our son, before they came along, I didn’t know that kind of love was possible. I want to grow old with them. But I’ve recently figured out I’m polyamorous, and I told Darin, and he had said, ‘If you wanna go out with other people you do realise that we’d break up, right?’ And obviously, that’s the last thing that I want. But I feel really strongly that if I don’t explore my polyamoury, I’m doing myself a disservice. I feel like some part of me is saying, ‘You have to do this, if you don’t, you’re killing yourself.’ And there’s this guy, who I’ll refer to as Fireball, who I like and who likes me, and I did our natal chart for compatibility and we’re basically made for each other, unlike me and Darin’s which was 3/4 negativity and challenge.

My question is really, I feel like I need to do something about my polyamoury, like if I don’t, I feel like my Soul is dying, but my partner isn’t cool with it, and I have no idea what to do.

Thanks,
–I Don’t Want to be a B*tch to My Fiancé

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Dear Captain,

My partner and I have been together almost a decade and our relationship has been polyamorous all that time. For the most part (aside from perhaps two ‘near misses, completely, in fact) it has been me in other relationships (my partner has never been interested in looking, or hasn’t reciprocated others’ advances). Our stated ‘rules’ have been around safer sex, and a rule of not getting involved as someone’s affair. The latter rule sprang from me entering the relationship with her fresh out of BEING someone’s affair. We both decided we didn’t need that – there was potential for drama that would involve each other etc.

After almost ten years my partner just met someone (someone she already knew but who just declared an interest) she really wants to pursue something with. The catch? He’s married. of course. She tells me she doesn’t really care about the ‘affairs’ rule now – she knows I do but she doesn’t see why she can’t do this, given that it’s so rare for her to have these feelings.

It’s the first time she’s got this close to seeing someone and so I can’t work out what are my feelings about it being ANYONE, and what are my feelings about her becoming an affair.

I have two choices. I can either tell her not to do this (and I believe she won’t) and she will be miserable and resent me, or I can NOT do that, and I will be miserable.

This isn’t ethical non-monogamy to me. it’s not what I signed up for. I love her, but I’m aware that my thought processes have changed. I cannot currently say I feel proud of her, for example, and I hate that.

I guess I’m looking for some perspective?

Sincerely,

Not where I thought I was going (they/them)

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I had a bunch of travel in July and never got that month’s version up. So, here’s another round of that thing where we answer people’s search engine queries like blog questions.

1 “Awkward coworkers who wont get hint

.”

Hints don’t work. They just create a sea of plausible deniability for clueless people to splash around in while you get more and more frustrated. If you want your coworkers to understand or know something, you gotta say it, as briefly and directly as you can.

2 “Is it bad to break up with someone after a day

?”

It’s no fun for anyone to break up after a day, but it probably beats the alternative of continuing to date somebody you don’t want to be with and lying to them about it for more days. You get to change your mind! Do the kind thing and tell the other person now.

3 “Should you notify your estranged father of your wedding?”

I would say that if you’re estranged from your dad, you certainly don’t owe him an invitation or an announcement. If you do want to tell him, I would also keep my expectations very low about what he’ll do. Weddings and funerals and baptisms don’t fix the stuff that’s wrong in families (& often exacerbate it), so what are you really hoping will happen if you give him this news? I wouldn’t count on any of it happening.

Weddings are one of those things that really show it when “cherished fantasy of what a parent should be and do” and “actual parent” don’t match, and I’m sorry that a happy occasion is causing a new sting of grief for what was supposed to be.

4 “What to do if hubby abuses because of MIL?”

Ouch, what a gutpunch.

Whatever your mother-in-law has done or whatever she is like, your husband is still abusing you. Until he stops, gets some help, apologizes, and changes the behavior, it’s your husband’s fault and his responsibility, and offloading the blame or an explanation onto his mom doesn’t change the fact of what he’s doing. I hope you can talk to someone about getting yourself to safety. Here’s the number for the USA National Domestic Violence Hotline.

5 “What does it mean if a guy says I have a girlfriend at the moment.”

It means some version of “not you, not now.”

6 “My husband thinks I should work out more.”

Lots of people should probably work out more and wish they worked out more. Lots of people should also stop telling other people what to do with their bodies. Do you want to work out more? When and if you do, that’s when you’ll work out more. You are the boss of you.

7 “An sms to a boyfriend who treats you like shit.”

A. “Bye! We are broken up now. Leave me alone.” B. “New phone. Who is this?

8 “Why does my husband get mad when I touch myself.”

Who knows? Insecurity? Mistaking marriage for ownership of you & your body?

What I know is that you are the boss of your body, including your sexual relationship with your own body. You don’t owe your husband an accounting of your solo activities. They are none of his business.

9 “While using a dating site should you be upset seeing someone you’re talking to off the site.”

On the one hand, the people in the dating site don’t live in the site, hanging upside down like bats at OkCupid headquarters to sleep at night, and it is quite possible to encounter a potential date-friend in the wild. Sometimes the world can be very small.

The “upset” part comes from, how does everyone handle it when it happens? Do they act weird and overly familiar and talk loudly about where they know you from, like it’s your kid’s parent-teacher conference and the teacher is like “Kid, you didn’t tell me your mom was a babe! I totally swiped right on her!“? Or do they say “Hello, nice to see you” and act calm and relaxed and safe? That’s all good information to have.

Or, do you feel like they are trying to figure out where you work and live and hang out and you get a stalker-y vibe from it, like they were seeking you out, trying to run into you? That would make me pretty upset.

10 “I live in a condo and a neighbor constantly knocks on my door. How do I tell her to stop?”

Neighbor, please stop knocking on my door, let’s save that for emergencies where something is on fire or flooding or bleeding. If you need to reach me otherwise, please leave a note or use my email and I’ll get back to you when I can.” #hintsdontwork

Then, you don’t always answer the door, and if you do, jerk the door open and say “What’s wrong?” because you’re expecting an emergency.

11 “My boyfriend said he can manage my appearance.”

Your boyfriend appears to need a mannequin or Real Doll or a Barbie he can outfit as he pleases all the livelong day, and you appear to need a different boyfriend.

12 “My boyfriend is depressed and takes everything out on me.”

Depression is not your boyfriend’s fault.

Taking everything out on you is a choice he is making. Do you want to stick around to be mistreated?

13 “How do I make friends for my husband.”

If your husband wants friends, suggest that he try Meetup.com or take a class or find a hobby group or play a fun sport or volunteer somewhere. Then let him do 100% of the work of following through with that.

14 “I love my professor how do I know her feelings?”

I asked her her feelings and she said that she doesn’t love you back. She wants you to enjoy her class and learn a lot from it and then go and have a great education and happy life.

15 “Dating a married man is hard. You cannot call him.”

It is known. If things like “regular calling” and “not sneaking around behind someone’s back” are important to you, consider the non-married as your dating pool.

16 “Can you masturbate if your roommate is deaf?”

Back to school time! It’s not all study tips and deals on extra-long twin fitted sheets, is it?

Masturbation is great and you should totally do it sometimes! However, if you share a bedroom with a roommate, wait until your roommate is not home to rub one out, ok? It’s just polite.

17 “Is it ok to just stop at a person’s house without calling first?”

But…you could call? “Hey friend, I’m in the neighborhood, any chance you’re home and want to hang out for a bit?

If you want to know if you have a “just drop by!” relationship with someone, here are three indicators:

  • They’ve told you to just “drop in, no need to call!” using words.
  • They also drop by your house.
  • You’ve asked “Is it okay if I just drop by sometime?” and they’ve enthusiastically said “Yes! Any time!”

Even if those three things are true…I would still call or send a text. Again, why wouldn’t you? Are you being chased and need a quick place to hide?

18 “Can a girlfriend influence your teen son to be a bad person?”

I’m sure it’s possible? And if your teenage son is acting like “a bad person,” it might feel better and be really convenient if there is someone else to blame for all of it who isn’t your precious-sweet-angel-baby-boy?

But, again, if your teen son is acting like “a bad person,” then he is making choices to do bad things, and I think any conversation you have with him needs to not displace his choices onto the girlfriend. Focus on his behaviors and the choices he is making, please. Don’t buy into the narrative that how he behaves is the fault of others’ influences, and don’t let him do it either. He’s responsible for his behaviors, and no girlfriend (or parents) can influence him to act like a jerk without his participation.

19 “New boyfriend who makes you feel sad.”

“Hey New Boyfriend, I like you a lot but since we’ve been dating I feel sad all the time, so let’s break up.”

20 “Can I date an insurance agent?”

Pro:

Insurance agents need love too!

Con:

Your insurance agent is at work and he/she has to be that nice to everyone. So I wouldn’t like, replace online dating sites with calling insurance agencies for fake quotes or anything.

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Are you there, Mayhem? It’s me, Captain Awkward.Image description: Dean Winters as “Mayhem” from the Allstate Insurance commercials. He is a white man in a suit slumped in the back of a very damaged car covered in seat stuffing.

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Dear Captain Awkward,

Recently, my husband and I have been talking about taking a step to be more open in our relationship. We had made attempts to do this before, but we sort of jumped in without enough discussion and then had to pull back because if something hadn’t been explicitly outlined for him as being okay, his default was that it was and he would be willing to soldier forward regardless. It was a little more of a “better to seek forgiveness than ask permission” kind of a situation and I kiboshed that because I need boundaries to feel secure. Anyway, we have been talking and talking and talking and someone sparked his interest and so we talked about baby-stepping our way back into this situation with much clearer boundaries and I felt totally okay with it – until recently.

So this woman, I will call her Pandora, came over to our house for dinner and things were fine until she and my husband started to have some weird and ambiguous conversation about an appointment she had the next morning bright and early. This goes on for a while, so finally I was like “Hey! I’m in the room and I feel like you’re having a conversation around me and it is making me uncomfortable! What are you talking about?”, at which point, Pandora goes “Oh well I have a lot of drama going on in my life right now and it is just best that I keep some things vaulted.” Which like, okay, but then also don’t vaguely drama dump in front of me in my living room.
Anyway, she left and then my husband goes “You want to know what that was about?” and I said “yes!” because of course I do when baited with juicy morsels of gossip. Well it turns out that Pandora has been fooling around with this one particular couple when they do MDMA and now has started hooking up with the dude half of the couple without the woman’s knowledge. In fact, the appointment she kept referring to was a six am visit from this dude, who was going to hook up her secretly on his way to work.

For context, this info was dropped on me at close to 2 in the morning and I had work the next day, so I didn’t say anything in the moment, but I spent the whole next day thinking about it and it seriously made me annoyed and upset. Like do I think her morning secret hookup dude takes a large share of the blame for stepping outside his primary relationship as he is the committed person? Yes. But it genuinely bothers me that she was intimate with this woman, knew exactly what the woman’s boundaries were and what the boundaries within the primary relationship were, and then decided to go there anyway. To me, sex isn’t just something that happens, it’s something that you choose to make happen and they chose against the wishes of the other person involved which is sketchy as fuck. That to me shows a huge sign of disrespect and I told my husband that it really made me upset and uncomfortable to bring this person into our lives in an intimate way. My reasoning was that if she is so willing to do this to someone she has had sex with, I don’t see what would stop her from doing the same to me, a casual acquaintance.

At this point, he says that they have had multiple boundary talks and she has assured him this won’t be an issue to which I think my exact response was COME ON, MAN! Also, during this conversation, he insisted on trying to contextualize her decision in her other relationship by saying things like “We have no idea what that other primary relationship is like!” and then he also bomb-dropped that this couple is very close friends with some other very good friends of mine, so I can’t talk to them about this because they could probably figure out who I was talking about via context clues, and he said that I can’t tell Pandora I know because she made him promise not to tell anyone and it would implode his friendship with her if she found out she broke his promise as she would be really embarrassed. I again told him that if she is sneaking around with this dude, whatever the current status of the other primary relationship is, they know it is not kosher and that it actually really bothers me that this early in the game she told him to keep secrets from me which, I think, are important contextually. Also, I seriously can’t help but wonder about not only the emotional healthiness of this situation, but the physical health as well. Like I can’t really imagine a situation where she’s like “Yeah, the guy I am also seeing is sneaking around behind his partner’s back and is kind of a cheating scumbag, but he’s really fucking diligent with condoms!”?

Anyway, I told him I am not comfortable with him taking things any further with her in light of these things and he responded by saying that he feels like she has explained things to him to his satisfaction and that because he has self-control and he is a good judge of character that he thinks that should be satisfactory in in this situation. If I have concerns about this situation, instead of unfairly shutting it down and taking this away from him, I should trust him, or, I am still feeling uncertain, I can have a conversation with her directly about boundaries, however I would have to do so without mentioning I know about her cheating scenario.

This whole situation bums me the fuck out because I feel like Pandora soiled all of it with her bad relationship mojo. I mean I am not against him seeing someone else – that’s totally fine with someone who is honest and above board with all sexual partners! -I am against this particular boundary breaking person and he keeps harping on the fact that they have an emotional connection and I am taking this away from him even though things haven’t gotten fully physical between them yet.

So I guess my question is – what the fuck do I do here? At the end of our last conversation, I agreed that we would put a pin in things on that front right now, but like, with the way things are now, I cannot imagine what scenario would ever make me feel comfortable enough to pull the pin out. (Maybe if she broke things off with the downlow dude and stopped pulling sketchy shit?) I mean how can I possibly trust this person? I feel seriously backed into a corner here.

Yours sincerely,
Sick Of Dealing With Pandora’s Box

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