Dating in NYC

So, I broke up with my boyfriend of 4 years. He's a good guy, just not good for me. It still feels weird not to be wearing his ring. But I needed to move on, and there's no time like the present (especially after years of procrastinating).

But this presents a whole new problem for me: dating. I've not had to date since a year before I began dating the ex. I was in a relationship with a guy for a year before, and then I went out with, I don't know, two guys before I met the recent ex, who I was with for four years. Clearly I don't know anything about relationships except that I'm not good at them. But that part of it is ok. What I'm really not good at now is dating.

I don't really understand how it all works. Ray Romano has this funny bit that was on Dr. Katz about not knowing whether he was supposed to hug a chick or kiss her on her cheek - it's kind of like the same thing to me. Like, what does one date mean? What do five dates mean? Is there even a point if neither person is looking for a relationship? Because for all that I can sign up for some casual encounters on Craigslist - and no doubt a lot of people do (especially in NYC).

This post was going to be longer but it's 6 a.m. and I'm still awake but I want to go to bed (which is what I get for sleeping until 2:30 p.m.). But I'm sure there will be more later.