Dating is a bitch

Believe it or not, I actually had two dates this past weekend. I’m not going to write anything about the first, which took place on Saturday night, since it went really well and I’m hoping to see the woman in question again this coming weekend.

But I'll happily tell you about the second one, which took place on Sunday night, while most of the rest of the country was being suckered by a huge corporation into believing that overweight men with IQs of 20 running around with a Humvee’s worth of protective gear on is entertainning.

For the past few weeks, my friend Jew had been suggesting that I call up her friend Jenna to take her out. I wasn’t crazy about this idea for two reasons: 1) Jew and I are just friends, although we did sleep together once a long time ago and so it seemed a bit strange to go out with one of her friends. 2) Blind dates just suck.

Whatever. I had Jenna’s phone number and so, while being bored at work last week, I gave her a call. We never spoke, but on Monday and Tuesday of last week we played phone tag and exchanged emails enough to make a date to meet at Taralucci e Vino near Union Square at 7:30pm on Sunday.

But when Sunday rolled around, I was still basking in the fun from my Saturday night outing and really wasn’t in the mood to go out with somebody else. But Jew had mentioned to me a few days earlier than Jenna was really looking forward to meeting me on Sunday night. And so I didn’t want to be a jerk and cancel at the last minute.

Jenna was a tall/slim brunette with long dark hair. Very stylishly dressed. She looked great. Except that she was wearing fur. With a matching fur pocketbook. It all looked fashionable and expensive, but I’m totally turned off by fur. I mean, I have a cat. And I love animals. So right now, she was batting about even: a plus for being gorgeous, and a minus for wearing a fur coat.

And then she made the bartender let her try three different wines, taking almost ten minutes before settling on one. She was polite about it and the bartender didn’t mind, but the high maintenance sign in my head was going off. This was reminding me of my old friend Rachel. In fact, I almost texted Rachel to tell her that might’ve met somebody more high maintenance that she is.

Anyway, Jenna and I settled in to chat over our wine. She had an interesting life story. Her family had moved from St. Petersburg when she was in high school, and they’d moved to Indiana. Then she’d gone to Stanford. Now she made a ton of money at a super huge investment bank. I was intrigued.And then she told me about a movie she’d seen last week. In excruciating detail. The whole plot. My mind began to wander. I told myself to pay attention. She might ask me a question, and I'd be thinking about Rachel in her lingerie. Or something Bill Maher said on his show this week.

But the story of the plot of this movie went on for a super long time.But after two glasses of wine, I started to have fun. And we decamped to a restaurant and had a really engaging, engrossing conversation.

I don’t feel like going into much details but Jenna is extremely beautiful and sexy, and really very interesting and smart. I would certainly see her again, but I think that she might be a little bit "high maintenance" for me. We were out for about 4 or 5 hours. So... I'd like to go out with her again, but in the end I'm not sure if it's a good match. Although, to be completely honest, I'm quite attracted to her. Even in just a physical sense.

Interestingly, I had a date on Saturday night that also went well. I'm supposed to see that girl this coming Saturday, and very much looking forward to it.

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