Reader Question #47: Please solve all my relationship issues at once

Dear Captain Awkward,

Like many single guys, I have a number of women I am interested in. And each relationship is fraught with its own issues leading to none of them moving forward. Perhaps you’d like to help me solve all of them? If you can’t do that, at least help me figure out who I should still try to date and who I should write off as a lost cause or terrible idea? That would be real swell.

1) The Ex

I moved a few years back, so all of our conversations are pretty much online at this point. (I generally don’t answer my phone when she calls because if I did, she would call ALL THE TIME. But after a few years of this, she’s stopped calling except for rarely, so it works out.) She still loves me. And I still love her. And we’re both still attracted to each other. And this is all why we were dating in the first place. But she has NO IDEA what boundaries mean, and appears unfamiliar with the concept of “alone time”. When we were dating, I did not get to have my own life. It’s why I had to break up with her. It’s why I’m hesitant to get involved with her again. On the other hand, is it insane to let boundary issues ruin what is otherwise a good relationship with good sex?

Like the Great and Powerful Bob, Intern Paul also rocks the skinny mic

2) The Almost

A friend of mine who I ALMOST dated, but after our three-night stand (we, uh, sort of skipped the dating part) she was talking about kids and I basically said, a) slow the fuck down, and b) I don’t want kids. She said she couldn’t date a man who doesn’t want kids, and I didn’t really have a good answer to that. But then she contacts me every few months and says how much she wants me, and how perfect I am, and how it wouldn’t have to be right away, but if I would just want to have kids eventually, she’d be willing to move here. I could probably just tell her “I might want kids, so let’s see what happens,” but this would be a big ol’ lie because I DON’T want kids, so I feel like telling her anything else would be misleading. And it’s like every time she calls it drives me crazy because she’s all “I miss you, I want you, just tell me you’ll want to have kids,” and it’s almost like she just wants me to say it to make her feel like it’s okay to date me, in which case maybe I should just tell her it’s a possibility, but I feel icky about doing that especially if I’m misreading and she actually thinks liking her a lot is going to make me want kids, which, no.

3) The Married Woman

You probably see this and right away you probably think it’s a terrible idea because having an affair is bad. But this woman and I have been friends for about two years, and she has recently told me that she and her husband have an open relationship and would be open to starting something. This is crazy, right? Like, people who are married don’t just get to be with other people and have it be cool, right? Because this feels totally weird and crazy, but on the other hand I like her so maybe I should just get over myself? I DON’T KNOW!

4) The Co-Worker

I know if it goes badly, it is going to make my job a living hell, because even though we’re not in the same room, it’s a small company and news travels fast and I just don’t want to deal with it. Plus she recently got divorced, and I’m not sure she’s totally in her right mind at the moment. Those are reasons against. But she’s a fellow programmer who also appreciates old film noir stuff and whenever a bunch of us go out for drinks after work, I wish I could spend more time talking to her because I feel like we have a lot in common. I think if we weren’t co-workers, and she hadn’t just gotten out of a messy divorce, I’d totally try to date her. But maybe these are two good reasons to either forget it or at least delay indefinitely?

So do any of these seem like decent prospects? Should I just wait for someone with no issues? Or resign myself to life as a stereotypical lonely geek programmer?


Crap At Dating

Yes friends, it’s time once again for America’s favorite game show “DON’T FUCK THAT LADY!” where confused boys must decide between their better judgment or the irrepressible urges of their groin.  And here’s the host of DON’T FUCK THAT LADY, Intern Paul!

Thank you, thank you everybody.  I’m sure you all know the rules, so let’s get right to Door #1!

Let’s see, first we have a lady who has no sense of boundaries or personal time.  In fact, things were so bad that you broke up, moved away, and ignored all of her calls in order for her to get the message.  Do you know what women call men who berate them with endless phone calls, have “boundary issues”, but “still love them”?  Stalkers!  And even if this woman is just a person who is blissfully unaware of the concept of personal space, you’re still doing her a disservice by remaining in contact with her.  I would wager that she thinks  the phone conversations with you are a gateway to getting back together, when in reality you seem to be keeping her in your back pocket just in case you feel like it down the road.  Do both of yourselves a favor and end contact for awhile.  Oh, and…


Lady #2:  So your plan here is to tell her a lie in order to get her to come and fuck you.  Normally, this is just a bad thing that you should not do, but in your case the lie is “Yes, I want to have kids with you, you should move to come be with me.”  This is a TERRIBLE, HORRIBLE, NO-GOOD VERY BAD LIE and you should not make it.  Here are the two possible outcomes if you lie to this woman:

1.   You eventually confess that you don’t want kids at some point before she gets pregnant.  She will be very very hurt and very very pissed that you made her pick up her life to come be with you and you strung her along for a significant portion of her fertile years.  She will hate you and will be right to do so because you are a shithead liar.

2.   Frustrated that things aren’t moving fast enough on the baby front, she will “forget” to take her birth control pills and SURPRISE, she’s pregnant (and don’t give me any “I’ll just use condoms” crap.  When a lady you’re dating wants you to stick it in, you’re going to stick it in.)  Aren’t you happy?  This is what you told each other you wanted!  Only she was telling the truth and you were lying! Have fun with that unwanted child you now have to support for 18 years.  Also, you are still a shithead.



Lady #3:  Yes, open relationships are a real thing.  Lots of people in the world engage in them and make them work both for their own personal needs and for the health of their relationships.  If you decide that open relationships are not for you and you can’t be involved with someone “cheating” on their spouse (even though it’s not), then hey man, I’m not going to judge.  Different strokes for different folks.   However, the fact that this woman is married, in an open relationship, and has come out to you about it means she’s a mature and sexually confident woman who’s interested in you.  Do you know who are awesome in the sack?  Mature and sexually confident women.   Also the fact that she’s married probably means she’s not going to get all up in your business like Lady #1.  So, get over yourself and…


(also, just take her word on it and don’t ask if it’s ok with her husband.  That’s so gauche.)

Lady #4 is a bit more of a complex case.  The two problems you mention (her recent divorce and potential work weirdness) are actual problems, but they’re not insurmountable.  And someone you have a lot in common with that appreciates the work you do certainly sounds like a good time.  But still….so much potential for drama…  Really I think the best course of action here is to become friends with her and wait it out to see if the situation gets any easier (she makes a move on you, one of you gets a new job, etc.)  And I want to emphasize here that you should become friends with her only if you ACTUALLY WANT TO BE HER ACTUAL FRIEND, not because you want to have some emergency pussy in a glass case that you can break open sometime.  For down this road madness (aka “nice guy“-ness) lies.  I repeat, do not hang around this woman being “nice” and “helpful” if the only reason you are doing so is so that she will “owe” you sex later.

So yes, hang out with her outside of work more, become her (REAL) friend, and try to figure it out from there.  If things don’t work out, you still got a new friend out of the deal (plus, neat programmer ladies usually know lots of other neat programmer ladies).  As the Captain says, do you really want to date someone who isn’t cool enough to be your friend?


Lastly, your smattering of questions at the bottom.  To be honest, you seem like the kind of guy that really gets off on girls/situations that have a lot of drama going on, and this is not good.  I’m not saying you have to wait for “someone who has no issues”, because let’s be honest, everyone has issues.  You just need to be more discerning and find women that don’t have giant neon green issues blinking all around them (such as Clingor and Make-a-Baby have).  Also, the “life as a stereotypical lonely geek programmer”?  REALLY?  Dude, were you around for the late 90’s?  We totally won that war.  Geeks are everywhere, and our loves are now mainstream.  The internet has allowed us to find each other no matter what our strain of geekdom is.  There are a shitton of smart, computer-programming, RPG-playing, fantasy-loving, geek girls out there, but they’re not going to want to touch your peen unless you have some self-confidence and love who you are.  So buck up little camper and get some self-esteem about your own identity, that way you won’t feel like you have to settle for a woman with a boatload of issues.

23 thoughts on “Reader Question #47: Please solve all my relationship issues at once

  1. dear intern paul,

    i kinda love you (in a friendly, non- threatening, non-stalking, not pissing off the captain awkward, way) right now. the end.

    1. I remember the first time I saw a videogame ad on a big city billboard. We’d started to breach the mainstream. I just smiled to myself and knew our time had come.

  2. I freaking LOVE this show!! Let me hear it, ya’ll: DON’T FUCK THAT LADY!!!!

  3. I agree with most of this (especially #1 and #2), but I have to say about #3… ask the husband. Married Lady may just want to be cheating, and it ain’t worth boinking a cheating woman. Too much drama (though clearly this guy seems to like the drama).

    *cough* Not that I’ve uh, known anyone who fell for the “oh, my partner’s fine with that” or anything. *cough*

    1. Yes. LW should make sure he is Fucking That Lady ethically and that she isn’t lying to him. “Gauche” isn’t a reason to refrain from asking questions that could save this fellow a lot of needless drama. In fact, this was the only bit that just didn’t fit in with Intern Paul’s overall awesome prescription for less drama, with the ladies!

      1. I have been in open relationships where this has happened and it kind of skeeved me and my partners out. There were guys that literally said to her “Oh man, I don’t know about this. Can I call your boyfriend to ask his permission?” Which is gross and unsexy on a number of levels, implying that the woman you’re about to fuck is a liar and untrustworthy, and that her vagina was my property and she needed to get a permission slip to take it out anywhere. That kind of defeats the whole purpose of the thing, doesn’t it?

        Also, these were guys that I had never met, and had no interest in ever meeting, and my meeting them would go against the rules and boundaries my girlfriend(s) and I had set up for ourselves. So getting a phone call some evening from a random guy asking “Hey dude, can I fuck your girlfriend?” would not have made me a happy camper. Plus, no woman-on-the-side ever asked me “Can I check to see if this is really OK with your girlfriend?”, so I guess the potential patriarchal implications always stuck with me.

        By all means LW should do some due diligence and talk to Lady #3 about her lifestyle and how she and her husband handle it. I was just trying to say that when the time comes to get down to business he should not demand an OK from hubby in order to go through with it. Hey, for all I know they invite potential partners over for a nice dinner, then all three abscond to the bedroom where hubby gets to watch because he’s a huge cuckold.

        1. I see what you’re saying here, but at the same time, the LW isn’t “random guy” to this couple – he’s known at least the wife for 2 years. Personally, I suppose they can handle their open relationship the way you’re describing even if they bang their friends instead of having one-night stands. But I, personally, wouldn’t want to take it to that level without having a convo with the other partner, if it were a friends with benefits type of offer. Just a different perspective here.

        2. It’s worth noting that there’s a third option here — rather than going directly to her husband and asking, this guy could instead talk to the woman he’s wanting to date and say “Could I meet your husband once — maybe for five minutes, at your house, before our first date?”

          That’s not going around behind her back, it’s just asking whether the parameters of her relationship allow her husband to meet her boyfriends for just long enough to confirm that, yes, all is well.

          I know some open relationships have a “don’t ask, don’t tell” footing, and if she tells him that her husband would rather not actually meet her boyfriends, then he can accept that and either decide it’s not worth the risk, or decide he trusts her. But if he did get to speak to her husband (in her presence) for a few minutes, it might go some way to educating him about open relationships, which wouldn’t be a bad thing.

        3. Seems like what’s missing here is a blunt statement of how bad you think it is to learn that you’re sleeping with a married woman who is not, in fact, in an open relationship.

          My guess from reading the thread is that Intern Paul and CAD have very different estimations of how they would react to this revelation. Seems like Paul would say “wow, she pulled one over on me. too bad for her husband and too bad for me.”

          CAD implies, at least, that he would react to this news much more explosively.

          The reality is, if you accept “my husband’s fine with it” as sufficient evidence that the husband is fine with it, you’re eventually going to end up fucking a married woman whose husband isn’t fine with it. That’s clear. What’s not clear is how big a downside risk that is, and whether it’s one worth bearing.

          1. Exactly! And my advice was definitely geared toward this specific situation, which has to do with a long-standing, important friendship that the married woman would apparently like to turn into a FWB situation. In this case, I do not see the potential risks to friendships and feelings as acceptable.

            Now, if I ended up accidentally fucking a partnered person because we met in a bar and he disclosed to me he’s in an open relationship, I would probably not be that overly bothered by it.

    2. As a poly woman (also: married!), you can generally tell when someone is actually cheating.

      They’ll be evasive and weird about the marriage thing, so go with your gut when it seems off.

      Also if they claim “oh, it’s okay, it’s an unspoken understanding” or “she just doesn’t want to know but she’s okay with it!” then also do not fuck them (AFAIK I never slept with anyone who was not in a really aboveboard relationship).

  4. i’d like to add something about #2 –

    be REALLY honest with her next time you talk. TELL HER “look, i feel like you’re wanting me to LIE TO YOU, to just say “sure, eventually i MIGHT want kids” even though i KNOW it’s a lie, because you want me to say it so you feel “ok” about moving here. If kids are your main goal, please stop – stop calling, or at least stop pressuring me. i’m not going to lie to you and i’m not going to change my mind. period.”

    because it really sounds [from the way you put it] that she doesn’t actually *care* if you want kids, per se – she’s looking for rationalization. and, possibly [probably?] the chance to change your mind.

    i don’t ever want to ascribe the motive of “making SURE she gets pregnant” to a woman, because there are people who think this is ALL ALL women want, and go around screaming from the rooftops about how you should NEVER have sex with a woman because she’ll somehow manage to get pregnant and then stick you with child support and [somehow!] live the high life off the $400 a month you’re paying.


    just because 99.9% of women WON’T do this… there’s still that .01%. and i don’t know if she is or not.

    but either way, you NEED to be blunt. “I really like you, Lady, but there’s no way in hell i’m EVER going to want kids, so please stop NOW”

    also, why not get a vasectomy? i’m about to get Essure [not a tubal ligation; plugs put in my tubes so that ovulation may happen but that egg? isn’t going ANYWHERE]
    i HIGHLY recommend permanent solutions for anyone who doesn’t ever want children 🙂

    1. It seems like this guy’s Lady #1 and Lady #2 situations could each be greatly improved with some bluntness.

      Like, does his ex even know that he never answers his phone because she is super clingy? Does the FUTURE MOTHER OF HIS CHILDREN realize that calling him up and bending his ear about how they totally should reproduce is pretty boundary-crossing?

      Bluntness: live it, love it.

  5. The first thing i thought when i read #3: IT’S A TRAP!!!

    I’ve been fed the “open relationship” line before, my friends have been fed the “open relationship” line before, and it just seems like each time we do, some dramallama comes up and spits in our face. I see Intern Paul’s point about the gauchness but just…. be warned.

    as for #1 and #2: TERRIBLE TERRIBLE PLAN OH GOD DON’T DO IT MAN. The ex with the really great chemistry and the all the love but no sense of boundaries? I have been there and it does NOT END WELL. Boundaries are ABSOLUTELY on of the very most importantest reasons to end a relationship. Because boundaries are oh god so important and people NEEDS TO BE RESPECTING THEM LIKE ALL THE TIME. And miss wanna be baby mama? I don’t like going around calling girls crazy, because people like to call girls crazy when they show the least bit emotion, appropriate or not but OH MY GOD THIS GIRL IS CRAZY RUN. Anyone who is bugging a guy WHO SHE ISN’T EVEN DATING about having his babies when he has been quite clear on not wanting babies is….. not setting herself up to make even slightly good choices. People who don’t set themselves up for good choices are not ones you want to tie yourself to even the least bit.

    Please to be stop talking to #1 and #2 now? Please? They is not good for your life.

  6. I too have fallen for the “open relationship” that wasn’t exactly. It wasn’t fun to deal with the aftermath. Proceed with honesty and caution.

    1. Me too, and boy oh boy. Midnight screaming phone calls. Just be aware, if it isn’t OK after all? It’s highly likely to be ALL YOUR FAULT YOU HORRIBLE SPOUSE STEALER!!!!

  7. As poly person, these things can go badly; if multiple relationships are to work — communicate, communicate, communicate.

    I think monogamous relationships can work without superlative honesty, but if you don’t have it when you’re poly/open — it is unlikely to leave everybody happy.

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