I've tried to stop loaning money to friends, but replace by up'ing my giving of money to friends, to the extent I can/want to afford it. Generally, someone ask

I've tried to stop loaning money to friends, but replace by up'ing my giving of money to friends, to the extent I can/want to afford it. Generally, someone asking for a non-trivial loan is in a really bad place; your loan may likely not be enough for them to get out of it, for whatever reasons they need money now, it's probably not that unlikely they're going to be unable to pay back the money when they optimistically thought they would, the loan probably isn't going to change their life circumstances as much as they hoped. If that happens, are you willing to let it destroy your friendship? If yes, then why are you loaning them money in the first place, you apparently don't trust them enough or value their friendship enough to give them a personal loan, at least not of the size you gave them, a size which if not paid back would hurt you a lot. And if you wouldn't end the friendship if they didn't pay it back... why not just make it a gift instead of a loan? Maybe for less than they asked, for what you can actually afford to not see back without being resentful -- because that's what you'd be risking with a loan anyway. I learned this the hard way. Loans will ruin friendships. I sometimes say no, sometimes say yes, but almost always make the 'yes' a gift not a loan. Pay it forward, pay it back to me however you think appropriate with voluntary favors or helping me when I need it myself, but not expecting you to pay it back monetarily at a certain date.