Not sure what to do here. My dad is so generous and always picks up the tab for everything. He offers to pay constantly, to the point I feel guilty. It's too much. I get the check too and we seem to split it more now that I'm older and have begun insisting on paying. What bothers me is my adult siblings don't pay, or even offer. We are on a family trip and dad will take the check or I will and I'm starting to feel annoyed. On one hand, I've found myself not enjoying outings because I don't want (nor is it affordable) for me to offer to pickup so many tabs...dinner for six is a lot more than dinner for one. Add in entertainment and...I'm offering to stay in because I don't want to spend $100 a dinner or more. Dad acts like it doesn't matter but he has confided in me multiple times about his money troubles (he can't afford it either). Both my siblings work. Tonight he made dinner reservations and I'm already apprehensive. He paid for last night so I feel like it's my turn. My option is to say, we are on one check (myself and my kid) or I can take the bill (really don't want to) or I can stay in and not go to dinner (I did that last night). Stating that I'm going to just pay for me and my kid would likely offend me dad. I'm really not sure what to do here. Suggestions? Thanks!