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Earlier this week, I encountered a man who boasted of having run naked (and through sprinklers) across the 18th green. It was the agreed-upon tax of a lost best. I have no interesting bet stories to divulge, probably because I’ve already willingly engaged in the kinds of activities (the predictable ones, at least–the legal but insane ones) that are smoldering at the ends of well-placed bets; my little brother bet his friend $20 to eat a AA battery once, but they were intercepted before it ever went too far; however, elsewhere across the wagering universe:
- An NYC school principal lost a bet with a pack of seventh graders and kept his promise to show up to school in drag, causing the Post to cast shade.
- After losing a bet with his physiotherapist, Austrian skier Rainer Schoenfelder skied naked down the Lauberhorn.
- Canadian gambler Brian Zembic got breast implants as part of a $100,000 bet; he even kept them past the terms of the agreement.
Do I dare ask anything you’ve acquired or committed as payment for a lost bet, or in an answer to an accepted bet?
Myself and two friends lost (won?) a bet wherein we became the first set of male cheerleaders ever at my small school in rural NY. We ended up serving out the whole Basketball season with only one ducking out (due to grades).
Initially it was VERY rough. Long before the first game we found that doing it was much harder than it looks (an no, we didn’t have to learn any dance moves). Then of course there were the games… Given the size of the school the home games weren’t too bad (most everyone knew about how the whole thing started). But the away games were very rough… I think we were the only team in the league with male cheerleaders.
Ultimately it turned out much better than any of us feared. Of course spending alot of time with the schools most desirable coeds was a big part of that (coincidentally sharing locker room space on occasion, was a unforeseen bonus). But it became alot of fun, and by the end we had put together a few stunts (throwing girls into the air, and other “lifts”) that were being well recieved by the crowds.
Alas, with my male dignity still intact I am pleased to say I honored my end of the deal and have the varsity letter to prove it.
posted by witheld on 12-12-2007 at 1:45 pm
In high school, our assistant band director bet us if we won Grand Champions at specific (large) tournament, he’d shave his head in front of everyone. He had nice hair.
He lost, and the payoff was featured in our local newspaper.
posted by Erin on 12-12-2007 at 1:50 pm
My late grandfather had five brothers. They would split their time between Round Rock, Texas and a cabin in the Ozarks of Arkansas. Grandpa said they frequently made bets in the middle of winter in which the loser had to run around the cabin in the snow wearing nothing but a smile. This earned them the reputation of being crazy with the people in the town.
posted by Lisa on 12-12-2007 at 1:58 pm
No bets come to mind other than your standard gambling. But this reminds me of a show that ran on the BBC for a while, Ed vs. Spencer. Two roomates that have a weekly challenge, i.e. who can gain the most weight, who can make the most money, who do kids like more, and my personal favorite who can last the longest hand cuffed to the other person. The pently for losing, you have to do whatever the other person says. The premise of each episode is that one guy always fights fair, the other always fights dirty. I think Comedy Central is borrowing this idea for a reality show this spring.
posted by Andrew on 12-12-2007 at 1:59 pm
In our highschool we had one crazy goth guy that wore long black skirts sometimes.
One teacher always made fun of him and a bet was started the the goth would wear a full suit if the teacher came in in a dress.
The goth kid looked really good dressed up.
The teacher looked like a bald version of my grandma.
posted by Diane on 12-12-2007 at 1:59 pm
There was a Biology teacher at my high school who had a running bet with all of his students: If you get 100% on a midterm or final in his class, the next day, you are in charge of his wardrobe, shoes, makeup and accessories. If you get 100% through the entire class, he’ll hand you scissors and an electric razor as well–and he had a full, bushy beard and lots of hair.
I only saw him dressed in day-glo drag twice, and the second time, he was bald as a baby’s backside.
posted by jenny on 12-12-2007 at 2:53 pm
This isn’t a bet, but a game is involved. One night a bunch of years ago (I was in my 20s,) some friends and I were playing a game called “Deprivation.” The idea is, each player in turn mentions something that he or she has never done, and everyone who has done that thing must pay the deprived one a counter (we used M&Ms, if I remember correctly.) Person with the most counters wins the coveted title of Most Deprived Person. On one of my turns, I mentioned that I had never been to the circus, and scored heavily.
MONTHS later, my best friend told me to meet him at Madison Square Garden, he had a surprise for me. When I found out what was up, I told him I felt like I had the coolest friend in the world. He replied; “Thanks. I feel like a divorced father on visitation day.”
Cheers, Mike!
posted by Joe Maz on 12-12-2007 at 3:07 pm
I will take any bet that involves eating something weird/gross/huge. I was called on this bet many times in my college’s cafeteria. Usually it was the basics, everyone piled their various food items in one bowl, covered it with ketchup and marshmallows, and dared me a six pack to eat it all. No biggie. It was more fun when they dared me to fit massive things in my mouth… like an entire Belgian waffle WITH strawberries. Would you believe I did it? And won $20. And lost my dignity trying not to choke. It was worth it.
posted by Molly W. on 12-12-2007 at 3:10 pm
I lost my soul in a bet with my boyfriend. It was around Halloween, and we were in a macabre mood. The worst part is, he won’t give it back, and has pointed out that he is now able to gamble my soul in bets with other people, as its rightful owner.
posted by Jen on 12-12-2007 at 3:13 pm
A very long time ago, I bet friends that I would wear sandals from March Break to December 1, exclusively.
In Ontario.
Canada.
Each person in had to make a $50 donation to a charity of their choosing if I won.
I won the bet 5 years running.
And I still have feeling in my toes.
posted by Shale on 12-12-2007 at 4:18 pm
My highschool driver’s education teacher had a standing bet. If you could go for 5 years without an accident you could come back and he would take you and a signficant other out for dinner to the place of your choice… But any accident counted, even if you weren’t at fault.
Wouldn’t you know it that about 2 years later when some idiot plows into me at a stoplight (while I’m sitting still this wasn’t one of the first things to flash through my mind.
posted by Doug on 12-12-2007 at 4:58 pm
This isn’t a singular bet but rather an entire gambling experience gone horribly wrong. I was playing poker with a friend who, in an effort to keep games going, will ALWAYS give people markers. The problem is that he usually attaches some outlandish rider to the pact. I borrowed $15 and laughed when I read the note that said “I, Allan, do hereby owe Mike $15 and my immortal soul.”
Well I paid up the money but he went around telling everyone he’d won my soul in a poker game and that I was now unable to see myself in mirrors etc. One day he came in with an elaborately detailed plaque that “Soul” on the front with my name on the back. The only way I would get it back was if I’d play $5 high card with him. I relented and lost… I vowed that I would not fall further into this trap and swore off the whole thing. For about a week. Long story short, I kept losing high card and it took 5 games and $25 to win my soul back. The plaque now hangs on my wall.
posted by Allan on 12-12-2007 at 6:50 pm
My middle name is Thor. My father swears that he lost a bet in college, and will say no more on the subject.
posted by George on 12-12-2007 at 6:51 pm
My high school bus driver (small town, we only had one) made a bet with the student body during a pep rally…can’t exactly remember what the bet was, but for the 3 days of the State Boy’s Basketball tournament he had a wig and cheerleader’s uniform on. He actually took time to learn some of the cheers. I cannot believe that they even made those skirts big enough for his gut.
posted by Heather on 12-12-2007 at 8:02 pm
This wasn’t actually a bet, but I think it still works. My friends and I were waiting in line to see a movie on opening night, and so to pass the time were playing a game of “Spoons.” Well, we decided that the loser of three games had to go hug someone who was in a costume and then ask, “Do you want fries with that?” I ended up losing, so I ended up hugging a complete stranger. Strangely enough, one of my girlfriends ended up knowing the guy.
posted by Janel on 12-12-2007 at 10:16 pm
I plead the 5th
posted by aaron on 12-12-2007 at 10:57 pm
When I was in 8th grade we had a terrible football team. So our 8th grade coach, who was obsessed with his looks decided to to make a bet with the team. He said if they went undefeated the whole season, he would shave his head bald.
So at the final game of the season, we won and went on to become district champions for the year. You could see it in his eyes, he was happy we won but at the same time he hated that he made the bet.
Of course we had to have a pep rally and he lived up to his word and everyone on the football team got to shave a small parft of his head. It was classic.
posted by Adam on 12-13-2007 at 10:08 am
Come, have we forgotten Warren Harding? The man who bet priceless White House china in a poker game, and lost? (I wonder whatever happened to it.)
posted by Sillstaw on 12-13-2007 at 1:07 pm
Things I did for losing bets:
1) Skinny dipped in the hotel pool on new years eve (outside in PA)
2) Chugged a gallon of milk. When I didn’t finish in 5 minutes I had to jog a mile.
3) Had to do a “silly walk” (alal Monty Python) for 3 blocks in downtown DC.
4) Had to add “cheese” to the end of every sentence throughout a 2 hours meeting. (”The figures we found were different cheese. We determined it was a rounding error cheese.”)
5) Drove 120 miles to the beach in a convertible (with the top down) without wearing pants.
Things others have done for losing bets to me:
1) Ate 10 pounds of french fries
2) Crazy glued a shirt button to their forehead for a day.
3) Had to clean my bathroom and fix me a steak dinner (She was vegan)
4) Had to wear a perfume/deodorant of my choice to work.
Some of the bets I have entered:
1) Bet I couldn’t eat only pizza for a week. (I did)
2) Bet I couldn’t jump my bike over a creek. (I did and loser and to lick a rock in teh creek)
3) Bet I wouldn’t scream “I love you, Oprah!” to a large woman sitting next to me on subway. (I didn’t- hence my “silly walk” above)
4) Bet I wouldn’t call in “healthy” to work. (I did)
5) Bet I could eat more pickles in 5 minutes than friend. (I lost- had to chug 3 warm diet cokes)
6) Bet I wouldn’t go an entire date without holding hadns, kissing, etc. (I did and we ended up getting married)
posted by Sam on 12-13-2007 at 1:46 pm