Last night I went on a date with a girl I had been chatting with on OKcupid for a week or so (she's a redditor, hence the throw-away screen name). I'm a 25 year old guy, she's 24.

We met up at a coffeehouse. I tried to get there late, but she arrived about two mineuts later than me. I was friends with the barista, which was a nice DHV. We talked for an hour or so over a glass of wine. I asked her questions and she would go on for a while telling her stories (largely about malware analysis and the large tech company she works for. Cool!). When she asked me questions about my work (which is technical and I talk for hours and hours about) I tried to give short interesting answers without giving too much away immediatly. She was laughing at my puns and jokes, and a few people came up to say hi to me while we were there (yay small down DHV's!).

Things were going well, and when the coffeshop staff started pulling our audio equipment for late-night music I suggested we changed venues. We walked downtown (I tried to work in some light kino here) for a while and she suggested we go into a Mexican themed bar to get Margaritas, so we did and hung out there for a while. This stage of things was really nice, we had a fun dynamic and were laughing a lot, starting to get a bit tipsy. It turned out we spent time at the same college years ago. She told me about her not-publicly-visible piercings, and we talked about weird people on online dating sites. She bought the drinks, immediately pulling her card out for the tab, which I thought was great. She also drew a "cootie shot" on my hand and started touching me more. During this whole time she was getting a text message every couple of minuets (and saying how annoying that was) from some co-worker friends who were across the street at another bar for karaoke. She after we finished another round there we went to meet up with them (with kino on the way).

So we go to the karaoke bar and meet her two guy friends, one of whom I had met in passing and was apparently an ex-boyfriend of hers. I engaged them in conversation and it was all pretty amiable, but she was sitting on one side of a booth with the ex, and I was on the other side with the other dude. We went out for a couple of smoke breaks, she sang some karaoke songs (holy crap she can sing), and at some point I started sitting on the other side with her for a while. I did a karaoke song (first time I've ever done that) and was f-ing awful, but I tried to have fun with it all the same and admitted it was my first time.

Around midnight the other dude (not the ex) took off, leaving her and the ex on one side of the booth, and me on the other. I was a bit drunk at this point, and getting kinda frustrated with the direction this date was going. They both put themselves on the list to sign more songs, but the list was looong so I would have been there at least another hour before they sang. I had to be at work at 8 in the morning, so around 12:30 I decided to take off. I thanked her for drinks, she told me to call her as I was leaving, and I was gone. I feel like I could have been a bit warmer in my exit (I was smiling and trying to be confident in my demeanor) but I was weirded out by the situation with the ex and didn't want to burn into stay up all night dealing with that. Maybe I should have stuck around longer and tried to isolate her from him, but being that we just met and I'd like to try to get into a casual dating situation with her, I didn't want to push too hard and come off as needy or desperate (which I'm not, I've got another date with another girl tomorrow night.). I ran into a bunch of friends on my walk back home, and text messaged her about how easy it is to run into people in town (we had been talking about that earlier) and that I had a good time. She texted back that she had a good time and I missed her last karaoke song and her getting "high fived by a thousand douche bags." I figure I'll call her tomorrow night before my date with girl #2 to try to set something up for Saturday night.

So what do you all think? Overall it was a good time, but the segment at the karaoke bar threw me for a loop.

tl;dr: Met girl off okcupid for first date, had a good time, ended up hanging out with her ex-boyfriend at the end of the night and it was weird.