Lunch with my broke friend...
I invite BrokeFriend out for lunch or dinner every month. I've known her for probably 20 years, and she's always interesting to talk to: she used to have "real" jobs that earned her a living. Now she's 65, penniless and living on social security and whatever work she can find.
I get a desperate text from her every few months that she doesn't have the money for rent, so I "lend" it to her, knowing that I'll never get paid back. It's okay; I just see it as supporting an artist, which she is, in a way.
BrokeFriend is a writer and I paid to have her book published; it's religious based poetry, and it's pretty good. Very inspirational, and at times, very funny. She sells some books when she does readings, and it earns her some coin.
When I first started giving her money, I didn't know where it would end. Now I'm sort of resigned that she'll always need me to float her some cash a few times a year. It's fine: I can afford it. I even put in a note in my will for my kids to continue to help her out, should I pass before her.