Lol this is like something one of my girlfriends would tell me about, which I'd respond to with something like "sounds like an asshole who doesn't respect you - move on."
Of course, they would then ignore my blunt but sage advice, end up getting drunk texted and become said jerk off's good time girl in between sobbing to me wondering why he doesn't love her.
Anyway, there's nothing wrong with a "$90 dinner" spent on someone he's not exclusive with. IMO, it shows class if a guy does that at any stage in the relationship, whether it be courting or serious.
Move on, conne!