A few bucks here or there. No big deal. I don't care if they don't pay me back that $2.19 I spent on their slurpee. We're friends. Friends do stuff like that.
Larger quantities of money is an entirely different thing. I haven't had to lend much money like that in a long time so I don't know where my cutoff would be. I used to have a friend who got himself into money issues and he needed money in his account at a certain date but he didn't get paid until a couple of days later so he was short. I'd loan him a few hundred for a few days. After three months in a row, I told him we have to stop because I don't to risk things going sour and he never asked me again.
I agree with the sentiment of everybody else here though. Money for a vacation? Nope.
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