Charity sentence
Fifty genuine compliments delivered to strangers per day for a week, tracked and occasionally witnessed by leaguemates. It sounds sweet until you're on compliment thirty-eight in a hardware store. Sincerity violations reset the day's count.
Budget note: this one costs nothing but dignity, which makes it a strong pick for leagues that would rather spend the pot on the champion than on the loser's downfall.
Seen in the wild: fantasypunishments.com
More charity punishments in the same weight class.
The loser volunteers as a bingo caller at a retirement home, weaving their fantasy failures into every number: 'B-9, like the nine points my quarte...
The loser enters a charity 5K or fun run, in costume, and must fundraise a league-set amount using props and public appeals. One documented loser r...
Whatever the champion donates to their chosen charity, the loser must match dollar-for-dollar, giving the winner direct control of the loser's wall...
In fairy wings and a tutu, the loser roams downtown feeding coins into strangers' expired parking meters for an afternoon, announcing themselves as...