Originally Posted By: motor_oil_madman
Originally Posted By: Fsharp
Tell him you're broke and need to borrow $200 ($160?)
It was $240 he paid me twice $20 each time so now it's down to $200.
Okay, $200 then. Ask him to loan you the money and if he gives it to you say, "Thanks [censored], that's for the $200 you still owe me. Good to know you have the money to pay me back." If he says he can't lend you the money nag him a bit about why not. This way you may either find out more about his money situation or he may give in and give you the money.
Alternatively, whenever you two are out somewhere together, like a restaurant, or store, or bar, and it comes time to pay; ask him if he's "got this." If he can pay for the both of you. If he objects or asks why remind him that he still owes you $200. Make sure to do this in front of an audience; preferably, mutual friends, his wife, hot waitresses etc.