This is kind of where I think modernity has it all backwards. Back in the old days when you had these kinds of vertical relationships where one person had several "rungs" up on the other, the one pulled the other up.
If he wants you there with him, as he is living his preferred lifestyle, he needs to back you up and cover you. You shouldn't have to ask. It's simple practicality. I'm assuming that he's used to having money and he should know that if he wants to date guys who haven't made it yet he needs to lend a helping hand now and then.
I can't stand cheap bastards. When I was younger and struggling I associated with some genrous guys who paid my way because they wanted me there with them at the operas, the ballets, the plays, the late night dinners downtown. I was good conversationalist, a good listener, an easy on the eyes escort to be seen with, and I learned to smile and nod a lot.
We need to get back to those kinds of arrangements. It made life interesting on both sides. I benefited and my companions did as well.
People that have are too damn selfish and paranoid these days, and people who have not are too self conscious about accepting gifts and generosity.
I can pay my own way these days, but I still never look a gift horse in the mouth.
