Who pays?
While we're talking about dating (I was, the day before yesterday, if you noticed), let me just say that I don't believe the guy has to pay all the time.
See? SEE? I don't demand much, am pretty easy-going, quite understanding, and very caring... some guy should snap me up quick!! 
Yes, well, anyway... 
...where was I? Oh right, I don't believe the guy should pay all the time. If he WANTS to, that's fine by me; I always tell people that I never say no to free food 
But my point is, he shouldn't be expected to. Especially if he's a peer and thus on the same rung of the economic scale that you're on. What I mean is, let's say you're both fresh graduates and you've both just started working, earning roughly the same salary... I just don't feel that it's fair to expect him to pay for everything. It would put quite a heavy financial strain on him. I would offer to take turns paying, or suggest going Dutch.
Of course, if he's earning a (much) larger salary than you, that makes things different, but I still wouldn't expect him to pay for everything. If he decides to do so, that's nice; kinda like a bonus 
But since I don't expect him to pay, if he does, it doesn't win him extra points in my book -- although I'll be deeply appreciative of the gesture. Heheh.