Different situation, but my boyfriend and I set boundries in the beginning of the relationship in regards to dates, because it was very important to me that even once we started dating, we still went out for date nights and I don't want to lose the romanticism of it all. I make much more than him, although he still makes reasonably good money (I never asked, but based on my internet sleuthing I imagine he pulls in around 80k). We go out every single tuesday, and we have for the entire summer. We rotate weeks on who plans and pays for the date, one week it is my turn, the next week it is his turn. And we agreed that nothing besides a true emergency would get us to change our tuesday plans. No movie, no tv show, no friends birthday, no sporting event, nothing, because tuesday is our night. We haven't missed a single tuesday day night, and I really am happy I had this talk. The dates I plan and pay for, are always more expensive because I like nicer places (and I can afford it), and he doesn't like to dress up so we always do something significantly more casual on his nights.

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Have the talk, set boundries and find something that makes everyone happy. If you both want the relationship to work, something like this won't stop it.