How does it work? The man I am seeing is more affluent than be by a lot. So far he has paid for large things, but I pay for some meals, tickets to shows, admissions tickets. I am ok financially and can kind of continue, but I don’t normally spend as much. Not his burden to provide for me and he is very generous (dinner, etc) but lately I have started to worry and thought how much easier it would be if we had more similar finances.