Dating sucks

Look, I could let the title speak for itself, but let’s go into some detail.

I broke up with a good girl in November 2008. I liked her, we got along well together, but deep down, as my mom said, we just weren’t going to wind up together. If it were kosher to break up with a girl you’ve dated for a year and a half over text message, we would’ve broken up a solid 6 months earlier. But no, even in today’s tech-happy world, you have to break up with people face-to-face. What bullshit.

Since then, here has been my dating history:

  • Random Plentyoffish girl: I don’t remember the girl’s name (which is probably because we never met), but we were talking because of a connection on a free dating site. She had 5 kids. She was 38. She worked at Walgreen’s. She blew me off because her cat needed some attention. Wow. Just wow.
  • Sarah: Met her from Match. One date. She said she was slender. She was not slender. I got the feeling that she was a drunk. Not that I have much ground to talk.
  • Erin: Another Match girl. Two dates. My friend labeled her a lesbian based upon her picture. If he had heard her voice he would’ve had even more grounds. Nice girl, no connection.
  • Diana: Ah, an interesting one. Dental hygienist’s twin sister. I should’ve known not to approach it when her sister told me she was crazy and that I wouldn’t be interested (mind you, I asked out the hygienist out 6 or 7 years ago). But no, I pushed it. We went out for a few weeks, I was getting close to finally getting some ass when we just sort of stopped contacting each other. We’d do text messages and emails back and forth until a rather nasty exchange while I was in New Orleans for a buddy’s bachelor party. I told her I didn’t know her schedule. She told me to fuck off. I called her a rude ass bitch and told her to call me when she wanted to fuck (I have no spine, but that is 100% truth). Surprisingly, we haven’t spoken since.
  • Courtney: Match girl #3. We dated for a month. She hadn’t had sex in 3 years (very rarely do I lose the “I bet it’s been longer since I’ve had sex” contest), so I knew I had to take it slow, which wasn’t an issue. We would do some petting, but no 3rd base action or anything like that. She told me I was pushing her, but I liked her so I slowed down. A week or so later she yelled at me because I was driving like I normally drive. I picked a fight (I was looking for an excuse, not because of the sex, but because I felt like I was the only one contacting her, and the feeling wasn’t reciprocal), she said there was no match, and I agreed. The next day, she showed up at my house and said she was ready for sex. I told her it didn’t make sense that the night before there was no match and it wouldn’t be right for us to have sex at this point. (I realize that a normal guy would’ve broken his dry spell and ended things after he fucked the girl, but, well, clearly I’m not normal).
  • Kelly: Kelly’s the one that got away. Friend of a friend, but I found her on Match. Serious trust issues. We dated for a month, I was much more into her than she was into me. She ended things by just not responding to calls and messages. That one burns.
  • Rebecca: Yet another Match girl. Things were going along fine, until she invited me to hang out with her friends. I showed up and it was her and 8 of her friends. Eight of her guy friends. No women. All dudes. I was quiet (partially because in a situation like that, I’m not the most outgoing guy and wait to be brought into the conversation). I left before she did, and her friends proceeded to tell her what an asshole I was for the next hour. The next day she told me the night did not go well. We broke up 2 weeks later. Fuck her.
  • Kelly 2: Still another Match girl. Liked her, introduced me to some good music, but I got the feeling she was never too interested. I was right. Two dates and done.

There have been other forgettable dates sprinkled in and an unfortunate (but apparently hilarious) incident in New Orleans, but in the end, I’m right back where I was when I broke up with my last girlfriend. And I haven’t been laid since.

Do the math. I’m 0-for-Obama. When I finally get laid I’m going to shout out, “Yes we can!”

I’ve always been someone that grows on people. A lot of people I know thought I was an obnoxious prick when they met me. (Now they just say I’m an obnoxious prick when I’m drunk and 40% of the time when I’m sober.) The problem with growing on people is that it doesn’t lend itself to great first impressions. So my confidence – which isn’t high in the best situations – when around women isn’t great.

On Opening Day, I was told by a friend that two girls had shown interest in me (looking back I can see where he’s coming from). I have so little confidence in myself that I was convinced he was fucking with me. A week later I seem to be getting some interest from a girl at the bar, but she’s with a guy, so I don’t approach it. Turns out the guy was her cousin.


I’ve been out with several women who have told me that in their past they would’ve slept with me on the first date, but they didn’t do that anymore.

Know what? Didn’t need to know that. If you’re not gonna fuck me yet, don’t tell me that you would’ve if we’d met at another time. Cuz, y’know, we didn’t.

My shrink has told me that I chase after emotionally unavailable women because of some perceived emotional distance between myself and my mother. We aren’t tight (when I see her pop up on the caller ID my typical response is, “Aw, crap.”), but I don’t know if I buy it. I lack confidence, for whatever reason, and I’ve watched too many movies that create an idealized version of what love and romance is all about.

So where does this leave me? Hell if I know.

I’m tired of making excuses. I’m trying my best and opening my options. I’m starting to realize that I’m more of a catch than I let on (hell, if nothing else I’m not a neanderthal scumbag like Ben Roethlisberger). And damn it, if anyone mentions their single sister I’m all over it.

But damn it it gets old sometimes.

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