Ethics, what do I do here (Semi-Poker Related) HELP

[xPuns1her]

Hi everyone, I came here for advice on this subject because I like the way people think on this site. Earlier today I got a call from my best friend back home, I'm away in college, he goes to a community college and is dropping out, anyway turns out he got a credit card recently and he bought some sneakers and alot of food and overdrew to the sum of $300. His family isnt wealthy and he dosnt have a job right now. Naturally he calls me first and tells me he needs a big favor and asks how I've been doing lately at poker. I tell him I've been doing alright and he proceeds to ask for the $300 and tells me he will pay me back this summer. I hate getting into money with friends because it ruins friendships.. however this is one of my best friends. I have a feeling that over the summer he would keep procrasinating paying me and it would snowball into a big issue. I'm completely lost on what to do here. He says he has no way of paying it except his parents whom he dosent want to ask. He says if he dosent pay it off then "collections" will come to him and thats "bad". Anyway, what the hell should I do here? I'm completely undecided and lost.