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What is the highest stakes bet you’ve ever made?

Asked at Massachusetts Street on March 22, 2008

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Photo of Brandon McKeever

“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.”

Photo of Erin Stewart

“I’ve been hit in the face with a pie because I lost a bet once.”

Photo of Lindall Cox

“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.”

Photo of David Koepsel

“Probably $100. It was over a dare; we’ll leave it at that. I did win, though, thank God.”


sunflower_sue 10 years, 2 months ago

Never lost a bet. :) However, the hubby had to pay up a giant bottle of Crown Royal to his best man because the hubby was the first "loser" to get married.

BrianR 10 years, 2 months ago

"Ha ha! You fool! You fell victim to one of the classic blunders! The most famous is never get involved in a land war in Asia, but only slightly less well-known is this: never go in against a Sicilian when death is on the line!"

matahari 10 years, 2 months ago

I've bet my firstborn many times over (too bad I never had oen, haha)

sunflower_sue 10 years, 2 months ago

guess I read the question wrong. The most I've ever bet was a home cooked meal to my hubby. Since I cook every day, I had nothing to lose. He lost and 15 years later, I'm still waiting for that meal. (Could a porter-house and twice baked be too darn difficult?)

camper 10 years, 2 months ago

We once bet a guy (our good buddy Andy) that we'd cover his meal if he ate a tablespoon of the yellow mustard sauce while at our favorite Chinese restaurant. He did it. We covered him. We made sure he had plenty of water. But it looked like most of the water we gave him was sweated out of his temples. After the ordeal was over, and though it provided much entertainment (especially the waiter and family seated next to us) I would not suggest this. Thankfully, Andy is doing ok today.

sunflower_sue 10 years, 2 months ago

R_I, I have no memory of that! (I must stop drinking.)

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