What were you thinking lending him $?

Neither a lender nor a borrower be. Shakespeare (Hamlet)
Shakespeare had it right. But people keep lending losers money and then wonder why they don't get paid back.
Before you lend someone money, you need to ask some questions.
1. Why are they asking you for the money as opposed to asking a family member? (Because no one else will lend them money, because they don't pay money back.)
2. How long have you known this person? (All of your life is the only good answer)
3. What is your relationship with this person? (Is this person just using you? Will they drop you as soon as they get the money?)
4. What are they borrowing the money for? (If it is not for food or necessary medical care, they can live without it.)
5. Why can't they borrow money from a bank or get a payday loan? (Because they have bad credit. Because they don't pay their bills)
6. If a bank, family member or payday loan center won't lend them money, why should you take the risk? (Because you have sucker written across your forehead.)
7. If a person has bad credit, there is a reason. IT IS BECAUSE THEY DON'T PAY THEIR BILLS. Can you just give this person the money and not expect it to be paid back? (Because you probably won't see the money again.)
8. What will happen if they don't pay you back? (Never lend money that you need back to pay your own bills.)
9. Will they sign a promissory note? (Make sure you get the terms in writing.) http://www.ilrg.com/forms/promisry.html
10. Will they pay you interest? (A bank charges a fee, why should you lend it for free?)
11. Why are they desperate and need the money now and can't wait?

Common sense says do not lend people money. You are not a bank. If someone you loved desperately needs money, then hire them to do some work for you. (Clean your house, wash your car, etc.)