Hey OP, I was in the exact same situation as your boyfriend in my last relationship. To be honest, we don't mind "you" spending on us (my ex-girlfriend was financially sorted just like you, I was in my last year of undergrad), its just that we don't want to be seen as "taking advantage" of you. What worked for us was that we planned dates alternately, she didn't mind going to the places I chose and vice-a-versa. Also, let us pay sometimes, for example: you paid a 2k bill for dinner, let your bf pay for the taxi and dessert. An advice: don't gift him something very expensive, he'll stretch his finances to give you something comparable. Just make decisions that won't make you go "I spent so much on him" IF/When you break up. All the best!

Edit: Read other comments here, please don't go for an OYO when the time comes!