Your best friend has been being drug to court over child custody a lot over the last couple years. He's asked to borrow money to help him keep partial custody of his kids. $200 there $300 here.. I've loaned him around $2k total during the time. He paid back the first 400. But hasn't paid back any of the rest. It has been 5 months since I last loaned him money. He post pictures on social media of taking his kids or his girlfriend out to eat or to the arcade or casino all the time. Honestly right now I've got $15 in my account. Yet I feel like I'd be a jerk if I asked him for money back. What would you do? Just wait for him to offer it back?