Always keep your first date very casual and cheap. Don't do dinner or anything formal like that. If you're doing dinner, do something really casual like a burger in the park. In NYC the best bet is to just grab drinks. Although everyone does it, it works.

With this in mind, here's a great approach I use when I grab drinks. For the first drink I say I'll grab it, but she's grabbing the next one. This typically works well for me because my typical date looks like this:

First Bar Drink 1 --> Excuse self to the bathroom and upon return re-orient myself into a more intimate position --> First Bar Drink 2 --> Bounce to Second Bar with lots of kino on the way --> Drink 3 you buy on the same terms --> Drink 4 she buys

At that point, you're probably going home with her. This is an amazing date schedule, it works like a charm. And you don't have to worry about who buys what.

Anyways, the point is that anything works as long as you use your judgment.