re: A good buddy called me asking for money yesterday. Update 6/12

Only give them money if you can consider it a gift, not a loan.

If the friend were creditworthy he would have already gotten money from a bank or loan company.

A similar scenario happened with a family member. They gave a longtime friend with a lavish lifestyle a big "loan" and it was never repaid.

It made things awkward for both families and put a real damper on the friendship.