Do MEN like women who initiate, plan and PAY for the DATE?

Ok, here's the sitch. Me and this new guy have been going out only for about a week. Our first date---he treated me to drinks at a plush city hotel restaurant....where I'm sure he paid atleast $40+ just for the drinks. Well---I told him I planned on taking him out next (even before our 1st date we both said we wanted to show each other the different spots we liked) well tonight---Im meeting up with him at my favorite restaurant where I plan to pay. Afterwards---I may also take him to this spot for drinks but am undecided whether he should be expecting me to pay or what...? Am I doing too much too soon. I'm not trying to show-boat that I got money, but am trying to be reciporical in that, I don't always expect him to pay for every outting. GUYS---does this give me points, make me stand out or will thi smake him take advantage of this? Do guys prefer "princess" women who EXPECT to be winded and dined all the time without paying?