Yeah, some people are incredible sticklers when it comes to their money but don't give it a second thought when they're the ones given a free ride...
I agree with you that your friend shouldn't be calculating the $15 but you live and learn I suppose.
It's good to be generous I think, and I'm like you with my friends, but don't be a fool. In your friend's case, fine, he wants to put the $15 into the equation... did he put the other stuff you paid for into the equation? Snacks, food, whatever... if he didn't, then remember that and do not be generous with him again. You're not his dad, you shouldn't be paying for his share just because you do it with other friends.
It's like the very first time I was given a lift home by a friend and upon arrival, was asked for $5 gas money... are you effing serious?
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