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A still image from a SuperMario game where Mario is trying to jump from the Friend Zone to the (much higher) Relationship Zone.

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There’s no way to turn off comments to individual posts, so we’re on the honor system here as of Friday, 3:45 pm CDT.

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Hello, Awkward Nation.

I get many versions of the question “How do I get better at meeting & dating women/men?” in the Captain Awkward Mailbag.

The answer is always some combination of:

  • Work on your social skills in general.
  • Dating is a crapshoot! For many geeks people that is incredibly stressful, because we like rules and being good at stuff. Give us the cheat codes! Tell us how to be good at stuff!  SORRY. IT IS TOTALLY SUBJECTIVE AND UNFAIR.
  • Your best chance is to throw out the weird sexist rules and expectations that you’ve inherited from romantic comedies, shiny magazines, beer commercials, and dipshits.  To quote Holly, “if you follow Cosmo’s advice, your dating life is going to be like trying to get asked to slow dance at the seventh grade socialforever.”
  • When in doubt, use your words.  Don’t infer; ask.  Don’t hint; say.

Fortunately, we have Intern Paul to answer today’s version of this question, and he can totally do it without a rantlecture about Jean-Luc Godard’s sexist portrayal of women as cruel childlike aliens who can never be understood (only desired) vs. Agnes Varda’s exploration of ambivalence or Vera Chytilova’s spectacular depiction of feminist rebellion as destructive play. Ahem.

Dear Captain Awkward:

I have a problem. It feels like whenever I meet someone I like and want to date, they like me back, but just as friends. I don’t mean that they tell me that as a polite way of turning me down, I mean that they are sincerely interested in striking up a relationship with me, but one that is completely platonic. Much of the time, that’s what happens. In fact, I’ve only had one serious relationship in my life (over ten years ago), but I’ve made about a dozen friends by asking out women I was attracted to.

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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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From meish.org

Everyone dies alone, cat wee or no cat wee.

Dear Captain Awkward,

My libido has largely picked up and walked off somewhere else. I’m waiting for it to come back from a trip to the corner store to buy cigarettes, but so far it hasn’t showed up.

It started in my late twenties after a series of flopping relationships and three years later I’ve hit my thirties and haven’t had sex in about three years.

The trouble is, I’m at a point where I’m looking ahead at the rest of my life and I don’t really feel like dying alone with seventeen cats. I only have one now, but we know how this story usually goes. Plus, while I don’t miss sex, I do miss affection and sleeping in the same bed with someone.

I also miss my younger, more libidinous self. She was a lot of fun and I have some great stories because of her, but I genuinely don’t know if she’s ever going to open the front door, Fantasia’s in hand, or not.

I’ve thought about exploring sluthood. I think it might have the ability to re-awaken my dormant sexuality. But unfortunately, where my body goes, my heart often follows and I don’t want to put my emotions through the kind of rollercoaster it might entail (which, now that I think about it, may actually be why I stepped off the sluthood boat years ago). On the other hand, there’s a whole world of human experience, monogamous or slutty, I am missing out on and I think that sucks.

Option #1 sluthood=libido=emotional rollercoaster/soul-sucking loneliness and despair/fantastic sex/valuable life experience. Option #2 long-term relationship=no libido=companionship/awkward sex due to lack of libido/inflicting my lack of libido on some poor guy resulting in relationship trouble, or Option #3 get another cat.

Are there other options I’m missing?

Thanks,
Conflicted

Dear Conflicted:

I’m going to try to answer your question without once using the words “get your groove back,” but you need to do me a favor, too.

I don’t know how cats became the ultimate metaphor for sad, lonely spinsterhood and dogs became the symbol for carefree happy couplehood, but cats are just cats and dogs are just dogs.  If you like cats, have a cat.

In my entire checkered past of dating, I’ve met exactly two dudes who were uncool with cats. One had a severe allergy.  Understandable. One made a joke about how he was hoping that I didn’t have a cat, since  I seemed really cool and he had trouble meeting cool chicks without cats, possibly as a Pick-Up-Artist-style trick to lower my self-esteem to get me to talk to him.  You know how you don’t get me to talk to you?  Pass off a shitty, lazy stereotype about single women in the hopes that I’ll try to prove that I’m not like all “those” women.  I was exactly like “those” women.  My answer was something like “Oh man! You’re right, I AM really cool, but I also have a cat.  Too bad!  We’ll never know what might have been.”

So your first step towards getting your mack back is to stop defining yourself as the the sad media picture of lonely single women whose singleness is a disease that needs to be cured and your cat is just one of the symptoms, like a furry tumor.  Even in a joking, self-deprecating way.  Even if Liz Lemon does it.

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