The money borrowing friend.
“I knew this guy that would purposely go out to eat with us and never had money on him,” says Vi, 23. “We’d go out to eat after doing something together and the first few times people would cover for him since he was like ‘Oh, I forgot my wallet.’ He never paid us back.”

How to deal: “Nearly half of all loans to friends and family members are not repaid,” Dr. Frankel says. “It's almost impossible to ensure ten dollars here or twenty dollars there is ever repaid without damaging the relationship. For example, you might say, ‘Hey, Susan, I'm wondering when you're going to repay that ten dollars I loaned you two weeks ago.’ Now this puts you in an awkward situation. So when ‘loaning’ these small amounts you might best consider it a gift if the person doesn't offer to repay it. When it comes to larger amounts, you want to put in writing the expectation of how and when it will be repaid. The other person should sign the ‘loan’ agreement. If you're not willing to do this, then you shouldn't loan the money because getting it back is pretty iffy.”