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?
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…
DON’T FUCK THAT LADY!
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.
DON’T FUCK THAT LADY!
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…
YES, FUCK THAT LADY!
(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?
DON’T (TRY TO) FUCK THAT LADY (YET)!
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.