Flirting with disaster

11/20/2009 10:32 AM

04/27/2011 10:39 AM

Hi. I'm a single 27 year old with a full time job in finance, an intense fear of commitment and terrible taste in women.

I'm no angel, but for some reason I have always found myself attracted to shallow, self-absorbed women. You know, the kinds of girls that spend three hours getting ready, order lobster on a first date and send at least five text messages during a movie. Most men enjoy finding themselves in this position because these girls are notoriously easy. "One dinner winners," one of my friends affectionately calls them. A few years ago I started trying really hard to avoid these simple sirens, but for whatever reason I can't shake the attraction. I call it flirting with disaster. You know the ship is sinking but you're going to sit on deck and play the violin anyway.

Personally, I'm looking for substance. It's nice to go out with a girl who can talk about something other than the current events on Entertainment Tonight. There are a few diamonds in the rough in Charlotte, but I can't seem to look past the easy and invest in something worthwhile. Have my MTV/Sesame Street/instant gratification generational flaws starting showing up in my relationship life?

I was sure I was on the path to recovery when I met Anna. We collided in the cereal aisle, where, trying to avoid an elderly couple, I accidentally ran my cart into the baby food and apologized as I tried not to blush. I said something stupid about being a big fan of Frosted Cheerios, and she convinced me to try the multi-grain kind. We chatted over to the milk aisle, doing our best to casually investigate the other.

When you meet someone new, you both play the getting-to-know-you game: Your mission is to find out if they are seeing someone without directly asking or using the words "boyfriend," "dating" or "promiscuous sex." It's harder than it sounds. Thankfully, she voluntarily mentioned her ex, and I got the nerve to ask for her number.

From the start, I was convinced Anna was going to be different. For once, dinner did not include a barrage of stories involving her cat, a 20-minute monologue about her crazy ex or an excessive usage of lip-gloss made from snake poison. She was a full-time student and said she worked a few nights a week as a bartender - usually a red flag, but it wasn't a career choice so I let it slide. She was smart and engaging, my friends liked her, and we even started talking about taking a trip to the mountains - and I wasn't freaking out.

Three weeks later at a bachelor party, my friend Paul tapped me on the shoulder and that's when I saw Anna - on stage. I begged my boys not to tell her I was there, but they were Christmas-morning giddy about the whole situation. I finished my beer and managed to get out unnoticed.

Man, I really liked this one.

A quick visit to the clinic the next morning left me wondering why I'm attracted to potentially disastrous women. Don't misunderstand me - I'm not judging her choice of employment. For some people it's a legitimate profession that keeps the lights on. Lots of respectable women have worked in "questionable" establishments to pay for college, and let's face it: There are plenty of girls who give up a lot more for a lot less on any given Friday night. I couldn't help but feel betrayed, angry and confused. In any other situation, my fear of commitment would have pulled the trump card and pushed her away. Most of the time I've tucked tail and run by week two, but wouldn't you know, the first time in a long time I decide to stick around - BOOM! Egg on my face. I have done my share of crappy stuff to girls in the past, but this went beyond karma. It was like kissing Sleeping Beauty awake only to discover she's the twin sister who works at the Men's Club. I guess when you take a chance you have to prepare to deal with the outcome, good or bad. Not every relationship works out, and the fact that most don't makes the ones that do so special. Hey, I'm starting to warm up to idea of commitment or at least not running from it. I still may not be the best at picking 'em, but at least my heart is finally in the right place.

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