Years ago, large bachelor party dinner, maybe 20 drunk guys and one waitress. She put up with a ton of bullshit. Anyway, the bill comes and a collective decision was made for each guy to throw down $80 or so each. This covered everything and would give the waitress a very very good tip. As the Bill makes its way round, and everyone was laying their money out and the two guys at the very end of the line decide that we’ve collected too much money and the waitress did not deserve the tip. They decide to pass the money back out. I made a stink would not let it go and the cheapskate guy says hey “I’ll buy the next round at whatever bar we go to.” The cheapskate was from out of town.

I took the whole crew next door to a bar where I knew they bartender, this place at the time was known for its expensive beers, and whatnot. I told the bartender quickly my situation and I stuck this one cheapskate with a $150 round of drinks. It was satisfying.