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As someone who loaned money I can sorta see where he's coming from...
I loaned my ex on three seperate occassions a lump sum of $1000.00 (while we were dating). I was never in a hurry to get the money until in the end when I needed it to pay bills and bail me out of car trouble. But throughout the entire year and a half long relationship I reminded him he owed me and you know what? He never paid! I kept thinking it was kinda shady that he could get back on his feet using my money and not afford to pay me back SOMETHING! Then it resulted in me needing money and not having it...stress, anxiaty (sp?) and tears.
Since you two are friends (sorta) I'd just keep an open line of communication. If my ex had simply said hey I can't pay you everything, but here's something I would have felt much better about the situation (and I feel that's what you're doing).
In the future I recommend never asking friends for money if you can help it. Some people aren't that nice and will hold it over your head for ever.
Good luck!
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