It very much depends on the people and the relationship. Through many years, I've swung a few hundred$+ in either direction with a bunch of people, thousands wi

It very much depends on the people and the relationship. Through many years, I've swung a few hundred$+ in either direction with a bunch of people, thousands with a couple. I much prefer zero stress - if money is tight, we just don't do expensive stuff, or steal the bill before they have a chance to pay. Mostly that means we stay cheap until we can safely cover multiple people if needed (running your safety-buffer low enough that you can't do that is a terrible idea anyway).