I had three dates on the schedule for this weekend: my second date Friday night with The Musician and then 2 first dates on Saturday.
The second date with The Musician went very well. We were supposed to have dinner at a place not too far from where I live. It was his choice. I’d never been there before because it has a reputation for being insanely crowded pretty much all the time and I don’t like waiting. Anyway, I got there a couple minutes after he did (not late, just a couple minutes after he did) and he’d found out that the wait was already up to 90 minutes for a table for two. We agreed that was crazy and I suggested someplace else on the same block. Actually, one of my favorite restaurants.
We have a lovely meal and great time. Our conversation was easy and fun and yet we managed to talk about some pretty serious topics. We’re just pretty easy-going around each other.
The food at this place is great but kind of on the heavy side and so neither of us wanted dessert. I was kind of hoping he’d suggest that we go someplace for drinks afterwards because it was still pretty early when we left the restaurant, but he didn’t. Instead I let him walk me home, knowing full well that I wasn’t going to invite him up. As nice a time as we’d had, I knew it would be a mistake to invite him up. He’s about to leave on a two week vacation. Sleeping with a guy on the second date who’s about to go away for two weeks is just a sure fire way to make things more complicated than they need to be.
We stood outside my building, talking, for a while. He didn’t make any kind of move and I really couldn’t read him. Was he just waiting for the invitation? Probably. I guess so. But it was wicked cold and so if I was going to invite him up you’d think he’d have realized it wasn’t going to happen after two minutes and said goodnight. Finally it fell to me. I said, “Well, I’m not going to invite you up tonight.” I stressed the word tonight so that it was clear that he was sure to get an invite soon. And then I told him thank you and I had a lovely time. He gave me a quick, very chaste kiss and left.
The next morning I was thinking that maybe I handled it poorly. I just don’t know anything anymore. I feel like my judgment must be wrong (especially as I post the Ex Files and review/remember the beginnings of that relationship-at the time, I thought everything about those first few dates was perfect and that didn’t keep it all from turning to shit). I sent him a brief, “thank you” email to which he replied with a thank you of his own and invited me out tonight (he leaves tomorrow). I couldn’t go because of other obligations and so that’s that.
On to yesterday’s first dates. I had two scheduled – one for 2pm and one for 6:30pm. The one at 2pm was with one of the potentially too young guys I mentioned on Twitter (for those of you who follow me there). He’s 38 and you know what – I can honestly say that yeah, he seemed really young. He didn’t online or on the phone but in person he came off as really immature and insecure (and yeah, he might still be that way at 48). He was smart, funny, cute but his insecurity was a real issue. He was one of those guys who was constantly pointing out how much smarter and better he was than everyone else. Oh, and name dropping. Which I really hate. I don’t care who you know. Really, I don’t.
My 6 o’clock date was a real nightmare. He suggested we meet at a bar in my neighborhood which I thought was very thoughtful. Then he mentioned a couple that he knew. One is just barely in my neighborhood, it’s actually too far to walk to. The other is one of my least favorite places. It’s cold and loud and overpriced. But he said he liked it and so I said I’d meet him there. When we were making the plans he said, “It’s on ___, right?” And then he mentioned the wrong avenue. I corrected him.
Well, he called me at 6:40 to say he was sorry but he was running late. I told him it was OK. I grabbed a seat at the bar and started without him. He called again at 6:50 to say he was lost. He’d gone to the wrong avenue. I corrected him again. I left the bar at 7 and started to walk home. When I was a block away I called him and told him I was on my way home. He had a fit on the phone. He said he was there and asked me to come back. I told him I wasn’t really in the best of moods anymore and just wanted to go home and would be willing to try another time.
He was kind of an ass on the phone. It wasn’t his fault he was late. It was the subway. And he didn’t have the right address. And…. And I should give him another chance. And I should come back. And the more he talked the less I wanted to listen. If he had just said, “I’m sorry things got screwed up. Can I make it up to you? Tonight or any other night?” Then we would have been cool. But instead he came off as a spoiled child. And then later than night sent a follow up email – half apologizing but half saying it wasn’t his fault and so I should give him another chance. Who knows, maybe I will? Maybe the pickings really are that slim.
Tags: Dating update, first date, second date