Haha! I don't know how dating works either. I'm probably a few months off before seriously getting into this, but I do think we can practice in the meantime. Get used to going to people to talk, try to keep the conversation going, perhaps even get a phone number or a coffee date. It's not necessarily a mainstream idea around here, by the way. It sounds to me though like you're there in your sitch.
One thing I would say about your message is that you should sound more self-confident. Right now, it says that it's unlikely he'll remember you, that he'll hangout with you only if he's desperate, etc. Just go with something more confident, where you appear to know your worth and yourself. "Hi! It was nice meeting you a Madison's bar. I seem to recall you just moved back, so if you're looking for people hang out, give me a sign." Also, sound like a girl who will not put up with boring or rude people. You're looking for quality, because you are quality, so he better keep his game up before you move on. I know that's attractive to me, much more than a girl who seems to think everything I say is funny.
I had a discussion with a friend of mine who's been dating for a long time (hasn't found the one) and she said that showing interest is very attractive. I'm also of the mind that it works 1/10th of the time, so let's try to get through the first 9 asap!
M39 D6 D3 (at S) S 2014-09 D 2016-09
"You can't start a fire sitting around, crying over a broken heart" - Bruce Springsteen.