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Three letters in one today. This will get long, but bear with us, ok? There is a soundtrack and a lot of talk about crushes and what they mean and what you should do about them.

First, a little song from one of our Awkward Patron Saints to get you in the mood.

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"Hi! It would be a terrible idea to get involved with me. Want to dance?"

I’ve got a post up at Feministe today about movie casting and stereotypes.  In retrospect I should have called it “Stop boring the shit out of me, Hollywood.”

Major Mishap is here once again to answer today’s question and take this letter writer to post-divorce friendship school, aka, don’t fuck that lady!

Dear Captain Awkward:

I’m recently divorced. (just over a year or so) My ex-wife was originally from out-of-state, we met on-line, she moved to my town to be with me, and we had a good near-decade run. At the end, she was pretty lonely, unsatisfied, and miserable.  I was never a “bad” husband. (no substance abuse, no infidelity, no physical/emotional abuse of any kind). I aint sayin’ I was good husband, I just wasn’t horrible. She was miserable and a saint to put up with me, totally justified in leaving, but this wasn’t one of those “put his clothes in a box, tape it shut, and light it on fire” kind of divorces. No kids, no money issues, no real animosity that couldn’t be suppressed.

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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?

Thanks,

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!

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