There are many times I did that kind of bet, the most common one is playing sport, either its badminton or futsal, usually there will be a pot and winner takes all, its not much but it increase the fun and the seriousness of playing the game and back when I was in high school we like to play coin toss and the winner win the coin, I played a lot of this mini bet for fun and I seldom won, so it can be said that I am losing money from this mini bet