Most Helpful Guy
If he was sacrificing his own fun to pay down his debt, and doing EVERYTHING he could to minimize his expenses to pay it down, and still needed some help, then, sure, you could help him out.
But he clearly isn't interested in sacrificing his own desires, and would rather you sacrifice for him. That's wrong, and if you do it, you are only enabling his poor behavior and bad decision-making - plus, he WON'T make paying you back any more of a priority than he's making paying back his current debt.
He got himself into this situation, and he needs to get himself out.
Most Helpful Girl
NO! Do NOT help him, don't do it! If he can go out spending then he cam repay what he owes, $5,000 is not that much in the grand scheme of things.
If you help him he won't change and he will do this again, how is he going to pay you back if he can't pay the debt back? Nope, please please please DO NOT lend him money.
Sit down with him and help him work out an affordable amount to pay back, an amount he won't struggle to find. That is the best thing you can do, giving him cash won't help. He needs to understand cause and effect. He needs to spend less so he can live on what he earns.