From your brief description, I’m a little confused at what the boyfriend asking — he wants to borrow money, but an “act of charity” suggests he won’t repay it.

I read it differently. If he was asking for a loan as an act of charity, that would imply he’s not intending to pay it back — that he’s looking for a gift rather than a loan.

But “Uncomfortable Friend” says the boyfriend wants to borrow money for an act of charity — implying, to me, that he wants to use the money to give a charitable donation to someone else.

Doesn’t strike me as much of a charitable donation if the money you’re given away isn’t your own! But this is where we really could have used more information. I have always been willing to loan money to friends or family if they were in a bad situation, but I would be less willing if they were just going to give it to someone I don’t know.