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Grant it it's neither here nor there, but for sake of argument: If you were the person who borrowed the money, how would you handle it?
It's easy to say I'd be generous but that's how I'd like to think I would handle it. I'd probably be more likely, however, to give my money away in the form of an expensive dinner and covering any expenses for the night than in just peeling off a couple of bills.
Really, that's the most I'd hope for from someone who borrowed money from me as well. As long as we're talking about "real friends", I'd be happier remembering "that time we went to the casino and you won and we blew like $250 on those steaks and drinks all night" than "the night you won and gave me $250 in cash".