and the winner was

…Craig?

Yeah, believe it or not I met a guy from craigslist whose name is Craig weird huh? I’m telling you only me. This date was a change of pace for me. 99% of the time I shy away from guys that are the same age as me. So for me to consider dating someone 23 is like once in a blue moon rare.

Saturday night the plan was to see The Hot Karl. He suggested dinner before hand, which I appreciated because he took the initiative. So we decided to meet up around 10:30 and had a bit to eat. First impression he is shorter than me, but only by an inch so I think I can live and he was thin, eeh, lets not jump ahead of ourselves I said its only just begun.

I was over dressed. But not crazy over dressed. I knew I should have just grab a t-shirt and sans the earrings. I need to take more risk. The conversation during dinner was pretty good; a moderate pace including world views and interest mixed a few awkward moments. Then the food came, I’ve never seen a guy be so picky about what he eats. He pretty much spent the entire time picking at his food until he was finally satisfied. I couldn’t watch after awhile and whatever he was doing I wanted no part in for fear I would comment. He promptly paid for dinner unlike that asshole Josh (still makes my skin boil thinking about it). Then we went to catch the bus. Now I know I claim to not be high maintenance 90% of the time, but its 11:30 on a Saturday night take a damn cab. So we get on a loud nosy CTA bus packed full of people. Finally we arrive at the theater. There was no show. Damnit! I knew I should have called ahead of time to make sure. So it was all about plan B.

We decided to take a walk back down Belmont. Chatting and even exchanging some playful banter. I still didn’t think I felt any real attraction. Finally we decided on grabbing a few drinks. It turned out to be quite difficult to find a quiet bar in Chicago at 12:30 a.m. we tried about three places and finally decided on grabbing a six pack and head to the beach.

This was such a change of pace for me. I was very surprised at his willingness to find a place where we could chat. I took that as an indication as him really wanting to get to know me. I have to admit I was starting to have a good time. We went down to the beach, grabbed a bench and just drank beer and talked. Then for some reason everyone in Chicago decided it would be a great place to hangout as well. We moved further to the water and sometime after the second beer. He asked me if I was interested in making out. I could have cared less at this point. I figured what the hell, because maybe that would help me decided if there was something there or not. We just sat there, I figure if you’re going to ask me if I want to make out and I say sure then maybe you should make the first move and he didn’t so I suggested we move closer to the water and of course the cops showed up. So maybe that’s not going to happen. As we walked back he suggested we hangout at his place (we were even finishing each others sentences and having the same thoughts at this point). I figured that would work until his friend who was visiting was outside on the stairs with some guy from the apartment upstairs. Next thing I know I’m hanging out with 19 year olds that are dumb as shit. I lost two hours of my life that I will never get back. This went on until 4:20 a.m. I went inside to pee and when I got out of the bathroom his friend was just sitting there on the couch. OKAY!! I guess my night is over.

He walked me out and opened his arms to give me a hug. I hesitated for a moment and then went in for the hug. He seemed disappointed. But at that point, nothing is going to happen no matter who you are.

So there I was standing at Clark & Foster at 4:35 a.m. trying to get a cab and not get raped, assaulted, robbed or even killed for that matter. At one point I thought I was going to have to walk the 3 or so miles home. I obviously made it home in one piece and of course as I went to bed the sun was rising.

There was my Saturday night in a nutshell a very long nutshell. I felt terrible the next day and sent him an email. I just wanted him to know that it was late and the flow of our evening was interrupted but maybe we could try a next time.