Reminds me of when I worked at a radio station when I was first married and bet my boss (originally from Wisconsin) that the Orangemen would beat the Gophers in the first round of men's NCAA basketball; the loser would pick up Dunkin Donuts for the station. Guess who was carrying donut boxes the next morning -- me! But Scott insisted on repaying me because he knew how little money I made and I let him, because he was right; we were pretty poor in those days.
Bets with bosses