[vinceguidry]

Talk frank about money with them, and build up good boundaries. If you need help learning how to say no, go hang out at a daycare sometime. There's a difference between being well-off and being loaded, loaded people can comfortably pay for the whole group's tab, the merely well-off can just buy his and his date's.

The main thing to keep in mind is to not take it personally. Also try to be more generous than you're used to being. It is a good thing to spread your wealth around, so long as you can keep it within the bounds of reason. It makes your life better in more ways than you can keep track of.

Another thing you might do is playfully adopt the alpha role. If they ask you to buy another round, you could sit back and be like, "sorry boys, daddy's all out of money, maybe you kids could go make your own," and have a good laugh about it.