The next time you’re speaking to him online, send him these 3 messages:
“Could you hold on a second? I need to send a message to my mom.”
“Hi Mom, i know we only need $27 more to get your heart surgery, but things are a little tight for me right now. Some jerk online owes me $27, and if that bum ever pays me, you’ll get your heart.”
“Oops, sorry, wrong IM.”
Send him a PayPal invoice and tell him it’s for his “convenience.” Or include a jokey note with it like “hint, hint” or “gimme my damn money, mofo!”
Say it while you’re joking around. Say, about the latest football game. After you two are having a roaring good time, like any friends should.
still laughing Be sure to whipe away your tears of laughter, and then hit him with this: “Wasn’t it funny when Elway dropped the footb–GIVE ME MY FUCKING MONEY–football? hahaha”
Subtlety. It’s what counts most in life.
I really wonder about all the people who said “let it go; it’s not worth losing a friendship over”. I figure there are two possibilities:
a) they themselves figure it’s ok not to pay back money they owe, or
b) they’re born without spines.
Ok, maybe there’s a third much-nicer possibility that I’m over-looking. But I can’t imagine how a person could be classified as a friend when they steal from you. Which is exactly what defaulting on a debt is.
Heh, just reminded me that a “friend” owes me £50 too. Its nice to know that he also owes this much to my sister and her b/f too. He only just started work this month after leaving uni’ (its only part time work too) and he won’t get paid till the end of the month. All this time a girl he’s been seeing, whom he tells us he doesn’t like and doesn’t want to be with, has been supporting him financially. But, she also owes my sister £100 and has been paying for this guy to go to see film previews and buying him video games for his P/S 2. Ontop of all this, the guy, his girl, my sister and her b/f are moving into a new house soon. The arrangement is that my sis and her b/f will share a room in this house since they’ve been seeing each other for so long but the girl is insisting that they share the cost of the house on how many are staying in it, not how many rooms there are.
Heh, isn’t money between friends great? 
“Neither a borrower nor a lender be…”
That said, remind him, telling him it is the last time you’ll mention it, and then forget it. He’s either a dead beat or has some other problem.
Wellllll, i already talked to him. But alot of the advice i’m getting doesn’t seem applicable to my situation.
Technically we aren’t friends. We are aquaintences who are on friendly, cordial terms. More than just people who get along but not friends either. We only know each other via the internet but we know each others names & addresses.
Also, he is wealthy. He made over 200k last year and if his new business picks up hell make closer to 400k in the next few years. $27 is nothing to him, he throws that kind of money around all the time. Thats largely why I charged him for the stuff I sold him, had he been a poor college student like me i would’ve just given the stuff to him. And i’ve seen pictures of his house so i know hes not one of those ‘pretend to be rich online’ people.
And i’m still 99% sure he just forgot to mail me money or is a procrastinator. he was very apologetic when i brought it up to the point where i had to point out that i didn’t want to embarass him, i just wanted to make sure he didn’t forget.