I don't remember where I read this, but a good compromise strategy for lending money you don't think you're getting back might be this:

1. Assume it's never getting paid back and only lend out money you're willing to lose.

2. Tell them if you get paid back in full, then later, they can ask for another loan.

3. If you don't get paid back, then consider it a gift, but no more loans to that person.

This way, you can continue helping people who are down on their luck but responsible about paying back, and you avoid being drained by deadbeats.