17 People Who Took a Bet and Instantly Regretted It

Sometimes, a simple bet can seem like a fun challenge or a harmless way to prove a point. But for some people, those bets quickly turn into moments of instant regret, whether because things got out of hand, the challenge is tougher than expected, or the consequences are just plain unexpected. In this article, we’ll take a look at people who took a bet and immediately wished they hadn’t.

• I bet my man $50 he couldn’t walk from the living room to the kitchen and pour a glass of lemonade blindfolded. He did it flawlessly. I paid up...and he actually kept my $50. I was devastated. © ninadelaflores / X

• I bet my girlfriend at the time that this guy she hung out with was going after her. Won that bet. She left me for him. © nfs3freak / Reddit

• While watching a movie with friends, my best friend joked that I wouldn’t survive a day in the wild. I was always the one no one took seriously, and I couldn’t stand it. He kept pushing, so we made a bet.
  Two days later, I moved into a tent in the nearby forest just outside town here in Canada. At first, it was way tougher than I thought. I seriously wondered if I’d made a huge mistake. But I kept at it, learning a few tricks along the way.
  In the end, I lasted longer than anyone expected—and won the bet.

• High school bet. I had to walk up to my long-time crush and say, “I’m in love with you.” The problem is, she took it seriously. We ended up dating for two years... until she found out it started as a dare. That breakup was brutal.

• [edited] Lost a bet on a Calgary Flames game when they lost to the Edmonton Oilers. I had to wear a feminine looking dress and a diaper to the sports bar for the next Oilers/Flames game. I had a sippy cup for my drinks that night.
  Wore it with pride. If I make a bet, I’m true to my word.
  My team won the game that night and my friend had to wear in 5in heels for the next game. It was so funny watching a 200-pound guy trying to walk in heels, I was surprised he didn’t break his ankle. © Graeme Cooper / Quora

• When I was in middle school, my math teacher bet the class that they couldn’t score higher than the previous year’s scores on a certain exam. He bet something unusual, though: his hair.
  This was made even more dramatic by the fact that he had little hair, and he promised that he would allow the other teacher to shave it, in class, while the class watched. Needless to say, we did win the bet, and there was what amounted to a public shaming ritual.
  He cried. It was very awkward. This is one bet that I would have been happy to have lost. It was made even worse by the fact that it never really properly grew back. © Unknown author / Reddit

• I had to wear the world’s ugliest prom dress to high school. It was neon pink. I am a guy. There are pictures, but thankfully this was before digital cameras became ubiquitous.
  The only copy is in the hands of my high school GF, who most likely has lost it for all time. © CFCrispyBacon / Reddit

• The bet was that I had to stick a 30 cm plastic green/orange toy arrow with a suction cup in the middle of my forehead during my next Teams meeting. I figured it would be fine since my next meeting was with an intern colleague, so I agreed.
  The meeting started, and there I was, with the arrow sticking to my forehead. My colleague laughed (not a big deal, right?). But after a few minutes, I removed the arrow, only to discover a big, round, 2 cm “hickey” left behind by the suction cup.
  Sure, I won 10 euros, but now I need makeup to camouflage my stupidity. 😅 © Ok-Succotash-66** / Reddit

• When I was 15, I bet my then-girlfriend that she would never be with another guy. She never has been. She and her girlfriend are getting married next year, and I have not been invited to the wedding. © PinkWhiteandGreen / Reddit

• I live in southern Kentucky, so snow is very rare. We’ll get a dusting at best. The news forecasted about 8-9″ of snow, and everyone at work was all excited about it.
  I bet the girl I sat next to, we wouldn’t even get an inch. If I was wrong, I had to make snow angels in a bikini.
  Obviously, I lost. I would pick the coldest day in 25 years to do that...and right after physical therapy from a car wreck. Not my finest moment. © ginger49 / Reddit

• A friend and I bet 50 bucks on our other friend’s marriage. I jokingly bet it would last 6 months, while he guessed 2 years. She cheated on him after 4 months, and he had a horrible time recovering from it. I won 50 bucks. © Unknown author / Reddit

• I once ate 14 cloves of garlic. That was my “I’ve made a huge mistake” moment of high school, anyway. Severe chest and stomach pain (“My heart hurts!”) was the least of my problems.
  I reeked of garlic for weeks. I was smellable from 50 feet away at first, and any washroom I used ought to have been shut down. I was on the track team at the time, but was asked to leave since I was essentially sweating liquid garlic. © Unknown author / Reddit

• A while ago, I had a bet with my father as to if I could drink this entire bottle of very, very, hot sauce. I have a very high tolerance for spicy food, but this was something else. The worst part, though, was that it hurt even more coming out than it did coming in. © Veryveryugly / Reddit

• It was Halloween and I decided to be Johnny from Ed, Edd, and Eddy. My costume was perfect. I wore a baggy white T-shirt with jeans and sandals, and I carried a piece of wood around with a smiley face on it.
  Lunchtime at my school had a costume competition, so I decided it would be funny to go up and compete. The other people that were up there were in ridiculous cosplay outfits (very impressive cosplay outfits, I will add) and I was up there in clothes I found out of my closet.
  The competition was completely applause-based. I won first place. I think it’s because I touched the nostalgia spot for all the kids who watched cartoons. It was amazing.
  I still feel bad for the kids I beat though, their costumes looked like it took them ages to make. I got a lot of angry looks from them. Oh well, I got a ’cut the lunch line’ pass out of it, so who cares? © Unknown author / Reddit

• When I was just a kid, maybe 8 y.o, my brother and I were eating ice cream. My brother said he could eat the ice cream way faster than I, so we had a race. I was certain he didn’t stand a chance.
  So I devoured my ice cream in a few split seconds and told him I’d beaten him.
  I then noticed he hadn’t rushed eating the ice cream at all. Then he told me, “Well, yeah, but I get the reward.” And pursued enjoying his entire ice cream while I hadn’t enjoyed mine at all, all wasted for a meaningless title.
  It taught me a valuable lesson, though. © minivergur / Reddit

• While in high school, my best friend bet me $10 that I couldn’t eat 100 Marshmallow Peeps in an hour. Made it to 83. Terrible bet because 1) It’s only $10 and 2) Haven’t been able to enjoy them since. © becoolimatwork / Reddit

• Back in college, I dared my friends with a tough brain-teaser and bet I’d go shirtless all day on campus if anyone solved it. Three hours later, my smartest friend did crack it, and I was embarrassingly paying the price. But then, things got super wild when people started to join me.
  At first, it was just a few curious onlookers cheering me on. But soon, more and more students began stripping off their shirts, turning my silly bet into an unexpected campus-wide thing. By the end of the day, what began as a silly bet turned into our most unforgettable day on campus.

If you found these stories surprising, wait until you see what happens in this article on unexpected story twists that change everything.