A Dating Story

I would like to start collecting dating stories from friends and strangers. To start, I am going to share some of my own.

The summer that my cousin got married (I think this was 5 years ago now?), I was in a dry spell. I was working a job I disliked. I didn’t know why I was feeling depressed. I made myself a mix CD of music that made me feel sexy and alive. I decided it was my “I’m getting some this summer” mix. That was the unofficial title.

Prospects weren’t looking good. I was “so over” my frustrating cycle of a relationship with my on again/off again fella. I had been flirting with a train driver but his work schedule was terrible so I never saw him so it was going nowhere fast. I was back at square one going on dates that left me feeling more empty than when I began.

I was a bridesmaid for my cousin. So when the parties started, I met her friends and her husband’s friends. One of her friends from college took a strong interest in me. It scared me, in the way that often women get scared when receiving attention. It wasn’t unwanted, it wasn’t inappropriate. It was scary just to be seen. Let me be clear that it was my problem, not his. He didn’t do anything wrong except flirt with me when I wasn’t ready to receive a nice guy’s attention.

He was also not my type at all. Picture Harry from Sex and the City, the one that Charlotte ends up with. These two would be twins.

So I would be extremely nervous every time there was a social event for the wedding. Because I knew I would be getting more attention. So when the wedding rolled around I got very drunk very early. I don’t know what I was thinking. Maybe it was all the champagne that we were getting for being in the wedding party (it was my first time as a bridesmaid and I was determined to live it up).

I was incredibly uncomfortable around the real-life Harry. And to avoid it, I end up flirting with some other guy. He had a beard and a rakish smile and he played hard to get. Boy, did I love to chase after men I wanted. I thought it was sexy. And I thought it was such fun to have two guys wanting my attention.

And I avoided Guy A by flirting with Guy B. Guy A kept pursuing but backed off completely. And at the after party who did I spend all my time trying to close the deal with? Guy B.

At the time, I also thought it was empowering to sleep with men whenever I wanted. So I took Guy B home with me. Which was incredibly awkward because I also drove my sister. And I had to drive Guy B back to the hotel the next morning. Weirdest walk of shame I have ever had in my life.

Guy B and I hook up. Guy B and I continue to hook up off and on for the summer even though he lives in Philly and makes me go up there to his dude apartment when we actually do see each other (which was two or three more times). I think one of those times I drove up there AND I cooked for him. I think it was under the guise that I lost some kind of bet, but it’s just wrong no matter how you slice it.

The sex was fine. Nothing mind-blowing. I thought this is what empowered women do. (for the record for anyone that thinks it may be: it’s not)

A year later, Guy B texts out of the blue and asks if I want to “hang out.” I have not become any wiser. I drive up to Philly where he takes me out for dinner and then drinks afterwards and we hook up at his apartment again.

And let me be completely transparent. I am a morning person. I often wake up way earlier than my bed companions. Thank god I know have Kindle on my iPhone because I will read. At the time I think I had a Blackberry. That morning when I woke up at 8  I didn’t want to be rude and leave before he woke up and ruin my chance at more sex or the chance to schedule another date. So I read Men’s Health. Three times.

That was the last I heard from him. And I was completely ok with it. I still wonder what would have happened if I had been less intimidated by Guy A. The last time I saw him at my cousin’s house warming party he was dating this sweet, pretty girl. I actually felt a little jealous. But that’s ok. Sometimes we have to go home with the bearded guy and have some really awkward encounters to learn your lessons.

I wish I could say I learned a lot from all the missteps with the bearded guy. I didn’t. It took me a long time to get the perspective of why I was doing everything wrong. But, that’s what makes for great stories to tell all of you.


Me and Guy A at the wedding. Yes, that is a look of surprise and terror. Yes, it looks like I am death-gripping his shoulder. I have no photos of me and Guy B- no surprise there.


One thought on “A Dating Story

  1. Pingback: A Dating Story — Single Gal Starting Over | The London Press

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