Every day this past baseball season I bet on the sport and put my dignity on the line. Every day I lose more bets than I win means a pie thrown in my face and a square of my choice from my Pick Your Punishment Board, which contains messes like a pie spanking, a bucket of slime, maple syrup, and naked pie barrage, to count a few.

This week, I pay off another slew of lost bets, this time wearing a single strap sports bra, which might be the most emasculating piece of clothing I've ever worn. And Then I had to do a seemingly impossible cupcake sitting Physical Challenge!

But after getting an ice cream sundae dumped in my pants, pied in the face, and slimed, me wearing my girlfriend's clothes was probably the least of my concerns...