What is the highest stakes bet you’ve ever made?
Asked at Massachusetts Street on March 22, 2008
“I bet my friend $1,000 to see how long we could keep growing our mustaches after last year’s March Mustache Madness. It never got paid, though. We both had plenty of excuses.”
“I’ve been hit in the face with a pie because I lost a bet once.”
“I bet my seventh- and eighth-graders that I would get a flat-top haircut if both teams won their league championships, and they both did. I wore it proudly for quite a while.”
“Probably $100. It was over a dare; we’ll leave it at that. I did win, though, thank God.”