As you might be able to tell from other posts, I am a fan of Missed Connections on Craiglist.  They’re fun, entertaining, and occasionally I’ll post on there.  Well, on Tuesday morning I ended up in a train car with 3 equally good-looking men (GREAT way to start the day!), so that night I put up a post titled “Do Business Men Read Missed Connections?”  I received a few responses, one of which I wrote back to immediately.  Our conversation went back and forth throughout the morning on Wednesday… little witty exchanges here and there, nothing with too much substance.  He asked if I wanted to grab a cup of coffee in midtown on my way home.  Since my cell phone is dated circa 2000, I don’t have internet on it, thus I didn’t get the email until I was back home.  We ended up agreeing to do lunch the next day.  A great sign I thought.  No alcohol, an actual meal with real conversation… maybe this guy is actually looking to date and not just hook up?

Thursday morning he emailed me confirming 12:30 at an Italian restaurant called Serafina.  I gave him my number, but didn’t get his in exchange, and when I got there 5 minutes late and didn’t see him, I was sure he was standing me up.  A little defensive on my part, I know.  I went to the bathroom to freshen up, and when I came back out, there was only one guy sitting there, who looked like a mix of Bradley Cooper from Wedding Crashers and the ghost of my past.  He was wearing a black pin-striped suit, light blue shirt, blue and light yellow tie, complete with cuff links.  I was beyond pleasantly surprised.  Both of us greeted each other hesitantly enough for any bystanders to realize this was definitely a blind date, but alas, there was no one around other than the hostess.

We were seated, I took one look at the menu and realized I couldn’t pronounce anything… déjà vu to dinner with the British Banker.  I seriously need to practice Italian pronunciation… I am half Italian after all. Haha.  I looked to him for suggestions and luckily he suggested the arugula and filet mignon salad. I was immediately sold based on the fact that I knew I wouldn’t fuck up when ordering it.  We talked about typical first date stuff- jobs, places in the city, why I moved here, etc.  He does finance, of course.  Although, he did go to law school, but decided against being a lawyer pretty much upon graduation.  I have yet to meet men who don’t do finance or law, but I guess I should complain too much.  The only caveat is that they think they’re hot shit.  He was really nice though, and had an amazing smile.  Nearly an hour and 1/2 later, we left and walked back towards his office, as I had some shopping to do near there as well.  We stood on the street corner for a good 10 minutes just talking.  It was one of those times where there are several attempts to close up convo, but then you get onto a new topic.  We finally said bye, sans a hug, kiss on the cheek, wave, which made me think he was just being polite when he said we should get together again.  10 minutes later he text me “Hey you!  I had a great time this afternoon.  We should do something again sometime soon.”

Great sign!  Texting ensued and then he started a joke about taking an afternoon nap together in midtown. Ugh. Bed talk? Really?  I sort of played along, though tried to politely deflect any conversation headed in a sexy, suggestive direction, although he was not deterred.  He asked about getting lunch tomorrow (which is now today), but I have a haircut soon, so now it’s been switched to Magnolia cupcakes and an afternoon cocktail.  That, I like.  A “midtown afternoon nap”, I do not.  I’d like to see how many dates I can go on with him, without hooking up with him, before he gets bored.

What irritates me (& Jenn) about this situation is the fact that he took me to a nice lunch, we had a great time, I was actually thinking there was dating potential, and he was immediately suggestive of hooking up.  He’s hot, I’ll hook up with him, that’s not the problem… the problem is I actually would like MORE than a hook up, and it seems men, or the men I like anyways (cocky, business assholes in suits), are not aiming for that. So this is dating in the city.  Nice lunch or two, maybe dinner, then the assumption that they’ve “earned” the supposed next step, sex.  No wonder the girls of Sex and The City were so cynical by their 30s.

At any rate, an update to come after the cupcake and cocktail date this afternoon.