Saturday’s Score = .500

I was a very busy SINgleGIRL on Saturday with two dates scheduled back-to-back.  First up was my second date with a guy I first went out with a week or so ago. He’s going to need a nickname because we have another date scheduled for tomorrow night.  For now I’m going to call him Mr. Red Flag because honestly, as much fun as I have with him, that’s all I can think about (read about our first date) when I think of him.

He has a small business and so has to work on Saturdays.  He invited me to come by and visit him during the day, and then he’d take a break and we could go out for a drink.  I thought it was a great idea for a date as it gave me the opportunity to take a look around his work (though I’d already poked around the website) and for us to just hang out in a pretty casual way, during the day.

It turns out we both had really late/drunk nights the night before and so instead of going out for a drink we went for ice cream instead (and you know how much I love a guy who can appreciate an ice cream date).  It was relaxing and fun and, again, I found him easy to be around.

But, and it’s a big but. I just feel really unsure if it’s a good idea to let myself like this guy.  I see him as being in a super-transitional stage in his life and I wouldn’t want to take odds on his still living in NYC one year from now.  For now, though, I think I’ll just play it by ear.  It seems kind of pointless to say, “no I don’t want to go out on a third date with you because I’m not sure where you’ll be living in a year.”

My second date was short and harmless.  This was the guy who I’d written off as a brain-damaged jerk but who then replied to my emails and seemed kind of sweet and cool.  We’d had a few email volleys and several texts back and forth and had been trying to schedule a date for a while.  This being New York, that can take a couple of weeks.

Anyway, he turned out to be one of those really intense, non-smiling guys who asked lots of inappropriate questions and wanted to talk about his bad history with women and online dating.  Whatever.  It was a drink and then I got to go home early.  I picked up some Chinese food on the way home and so that was cool.