I don't mind floating $20 here or there, or picking up the bar or restaurant tab with the expectation that everyone else will do the same at some point during the trip, but I'm not going to be an ATM for anyone. If I hear, "I'm low on cash" more than once from a person, I'm more inclined to offer to drive them to a cash machine than I am to continue lending funds. But that's just the banker in me.

Whenever I've traveled with others, I have to say that this situation really hasn't developed. I recently went to the Super Bowl with my brother-in-law, and we worked out all the cash expenses along the way and we split the hotel, airfare and rental car down the middle afterwards. No big deal.