When my date pays for things/establishes a trend of paying for things, it gives me permission not to fuss about money. I am very, very inclined to fuss about money if any of the money involved is mine, so I find it a huge load off my mind. (I go on first dates prepared to pay half if my date seems to prefer this idea when I ask, but preparing to do that before every date with a person I intended to see regularly would be rapidly exhausting for me, so I'd be leery of going on dates-that-could-cost-money with someone who doesn't demonstrate an inclination to pay - though this doesn't preclude 100% of possible second dates.)

Example: I recently dated a guy who took me out to movies (he paid), and we were trying to think of something else to do besides see movies. I proposed snow tubing, but then discovered that the only snow tubing place open in the area which had a device to pull the tubes up the hill was expensive. I dithered to him about this. If he had said something like "don't worry about that, I've got it", we would have gone snow tubing. He did not, so we didn't. (This didn't preclude another movie date after this non-event.)