multi-millionaire front, I’ve got (at least) three brothers in that category:
One pays for pretty much everything that he invites you to. Which is nice because some of the people shouldn’t pay for the kinds of things he wants to do with them (eg suites at games, some travel) but he’ll also sometimes ask for some favor in trade that allows you to feel like you’re not just mooching. An example of that is he wanted to do a SCUBA trip to the Great Barrier Reef with me, I’m not poor, but a last-minute week-long SCUBA trip to Australia is not something I’d normally try to do, so he asked me to make some artwork for his new house in return, which is what I do.
Another pays only rarely when it’s an occasion that he can excuse for it. He likes to save money where he can, but the real motivation here is he doesn’t like to make people feel like he’s better for having more money, and believes strongly in the feeling of self-sufficiency and doesn’t want to offend or take that feeling away from his siblings.
A third would pretty much always have each person pay for themselves and you’d never guess he’s rich by how he lives. He’s pinching the pennies way more than he needs to, but his attention to detail has made him a lot.
But all three would pay for a kid that they were with.