These 15+ People Made Ridiculous Bets And We Know They Are Regretting It

Choose your bets wisely.

Sophia

Published in Funny
1 Aug 2018

These 15+ People Made Ridiculous Bets And We Know They Are Regretting It

These bets started out like harmless bragging rights, but they quickly turned into some of the most ridiculous losses you will ever see. From dyed hair and goofy costumes to awkward public dares, the stakes got a lot stranger than money.

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What makes these stories so funny is how far people were willing to go after making a promise they probably should have thought through twice. Some of the bets were between friends, some were family challenges, and a few turned into full-on public embarrassments.

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By the end, it is hard to tell who had the worst idea, the person making the bet or the one bold enough to accept it. Read on.

1. "In 2001, my parents bet me that if I did not drink, smoke, or do drugs by 21, they would give me $1,500. Here I am on my 21st birthday holding the contract I signed when I was 8."

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2. "My dad challenged the students at the school where he is the principal to read a combined 1,000 minutes. The reward would be getting to push him down the hall on a tricycle while he wore mismatched clothes inside out."

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3. He challenged one of his campers, who has dyslexia, to read 10 chapter books in July, and then she could dye his hair any color she wanted. Well, she won, and now he is sporting pink hair.

4. He works with patients in a rehab facility, and two months ago he made a bet with one of his patients. If they helped him reach a certain goal, he would shave his beard. He managed to reach the goal, and now the beard has come off.

Some of these bets aged exactly as badly as you would expect.

5. "I won a bet with the library at my university, forcing them to hang a portrait of me until I graduate. Here's the photo I submitted."

6. Mom definitely won!

Twitter

7. Poor guy lost a serious bet.

8. This 61-year-old Swedish principal made a bet with one of his students. If the student could make it through 9th grade, the principal would dye his hair pink. Surprise! His hair is pink now.

That principal really committed to the deal.

9. This is what happens when you talk big, but your sister beats you in the match and the rematch.

Instagram

10. "Bet we can beat you at hide and seek, Uncle David!" Bet you can't.

11. He bet the girls living upstairs that he could fit into any clothing they could fit in. It's safe to say he won.

12. He lost a bet with his cousin; now his head is a pineapple.

13. This 86-year-old man challenged him to a pole dance contest at happy hour, and the older man won.

14. He made the mistake of telling his girlfriend it was impossible to stand a coin on its side.

Imgur

15. "My husband bet me I couldn't shave his foot without him waking up. This is what he woke up to this morning."

16. Challenged her kid to catch a seagull, and indeed he did.

At this point, nobody should be surprised by the outcome.

17. Someone bet him that he couldn't balance a pool ball on three pool cues. It's safe to say nobody played pool for the rest of the night.

18. She lost a bet, and now this is her senior picture.

19. He bet one of his parents that he couldn't touch his head to the ceiling.

20. "My teammate is a 5'6" gymnast. She bet us she could completely fit in her locker. She won."

21. "Lost a bet and had to go through airport security dressed as a dinosaur (TSA said I looked cute)."

22. This is what happens when a billionaire loses a bet.

Getty

23. Lost a bet to his girlfriend, and this was their costume this year.

24. He won a bet against his boss over a year ago. One day, he came into the office and found his boss had paid him back in pennies.

Some payback takes a little longer to land.

This feels like the coworker who asked for money after a lost bet.

25. Had a bet with his history teacher and lost.

26. This boss and coworker had a weight loss bet. The loser had to cross-dress, but that is his real hair.

27. Optimus Prime is quite a cool name for a kid.

Twitter

28. The band director lost a bet and had to wear a banana suit the whole day.

29. "My history teacher made a bet that if the student on the left got above a 95 on his test, he would shave his head. He got a 98."

30. Got drunk and bet his friend he could fit a whole box of straws in his mouth. He really didn't disappoint.

31. "When your dad bets $50 that the 'Physics in a Nutshell' ruler/hammer post is impossible."

32. He lost a bet, so he had to wear this 'bad boy' from Christmas Eve to New Year's Eve.

33. Bet his friend that he would not play dodgeball in a tutu. His friend won.

34. Poor guy lost a bet.

Instagram

35. This guy lost a bet, so he had to go on a first date dressed like this. I wonder if there was a second date.

36. Another guy who totally sucks at fantasy football.

37. He bet his roommate that America would win against Canada in hockey, and now he is freezing his butt off.

38. "We had a bet about our baby's gender. My husband lost."

39. "My 12-year-old cousin bet me I couldn't fit into his Halloween costume. Challenge accepted."

40. Don't lose in fantasy football.

41. This is certainly a unique type of bet.

Twitter

42. "My friend lost a bet 5 years ago, and his friends changed his name. He just found out it was actually accepted last week when his passport expired. He has to wait 3 years to fix it."

43. When she was a senior in high school, she bet her mom $1,500 that she wouldn't drink until she was 21. Well, she won.

Twitter

44. We don't think Carson Palmer has ever won a bet in his life.

Twitter

45. Dad and kid made a bet, but dad lost and had to dye his hair.

46. "We bet my grandfather he couldn't fit in my aunt's Lululemon shirt. He did."

47. "My friend Billy was challenged to beat his coworker's record of fitting 41 grapes in his mouth. Here's Billy with 42.5 grapes. Billy hates losing."

48. Michael Capuano from Massachusetts lost a Super Bowl bet.

Twitter

49. He lost a bet, and now he is stuck to a road sign in Wallisville.

Facebook

50. She lost a bet with her sisters.

Twitter

51. "My friend didn't think narwhals were real and lost a bet because of it."

Imgur

52. "My drunk friend bet me $20 he could catch an opossum. He won."

53. The ultimate punishment!

Twitter

54. Turned into a fairy because she lost a bet.

Facebook

55. "My friend's liberal dad called me a 'dumbass' for thinking Trump would win big league. He lost the bet."

These bets were never going to end quietly.

For another bet gone sideways, read whether she should have let her younger sister win family game night.

1. "In 2001, my parents bet me that if I did not drink, smoke, or do drugs by 21, they would give me $1,500. Here I am on my 21st birthday holding the contract I signed when I was 8."

2. "My dad challenged the students at the school where he is the principal to read a combined 1,000 minutes. The reward would be getting to push him down the hall on a tricycle while he wore mismatched clothes inside out."

3. He challenged one of his campers, who has dyslexia, to read 10 chapter books in July, and then she could dye his hair any color she wanted. Well, she won, and now he is sporting pink hair.

4. He works with patients in a rehab facility, and two months ago he made a bet with one of his patients. If they helped him reach a certain goal, he would shave his beard. He managed to reach the goal, and now the beard has come off.

5. "I won a bet with the library at my university, forcing them to hang a portrait of me until I graduate. Here's the photo I submitted."

6. Mom definitely won!

7. Poor guy lost a serious bet.

8. This 61-year-old Swedish principal made a bet with one of his students. If the student could make it through 9th grade, the principal would dye his hair pink. Surprise! His hair is pink now.

9. This is what happens when you talk big, but your sister beats you in the match and the rematch.

10. "Bet we can beat you at hide and seek, Uncle David!" Bet you can't.

11. He bet the girls living upstairs that he could fit into any clothing they could fit in. It's safe to say he won.

12. He lost a bet with his cousin; now his head is a pineapple.

13. This 86-year-old man challenged him to a pole dance contest at happy hour, and the older man won.

14. He made the mistake of telling his girlfriend it was impossible to stand a coin on its side.

15. "My husband bet me I couldn't shave his foot without him waking up. This is what he woke up to this morning."

16. Challenged her kid to catch a seagull, and indeed he did.

17. Someone bet him that he couldn't balance a pool ball on three pool cues. It's safe to say nobody played pool for the rest of the night.

18. She lost a bet, and now this is her senior picture.

19. He bet one of his parents that he couldn't touch his head to the ceiling.

20. "My teammate is a 5'6" gymnast. She bet us she could completely fit in her locker. She won."

21. "Lost a bet and had to go through airport security dressed as a dinosaur (TSA said I looked cute)."

22. This is what happens when a billionaire loses a bet.

23. Lost a bet to his girlfriend, and this was their costume this year.

24. He won a bet against his boss over a year ago. One day, he came into the office and found his boss had paid him back in pennies.

25. Had a bet with his history teacher and lost.

26. This boss and coworker had a weight loss bet. The loser had to cross-dress, but that is his real hair.

27. Optimus Prime is quite a cool name for a kid.

28. The band director lost a bet and had to wear a banana suit the whole day.

29. "My history teacher made a bet that if the student on the left got above a 95 on his test, he would shave his head. He got a 98."

30. Got drunk and bet his friend he could fit a whole box of straws in his mouth. He really didn't disappoint.

31. "When your dad bets $50 that the 'Physics in a Nutshell' ruler/hammer post is impossible."

32. He lost a bet, so he had to wear this 'bad boy' from Christmas Eve to New Year's Eve.

33. Bet his friend that he would not play dodgeball in a tutu. His friend won.

34. Poor guy lost a bet.

35. This guy lost a bet, so he had to go on a first date dressed like this. I wonder if there was a second date.

36. Another guy who totally sucks at fantasy football.

37. He bet his roommate that America would win against Canada in hockey, and now he is freezing his butt off.

38. "We had a bet about our baby's gender. My husband lost."

39. "My 12-year-old cousin bet me I couldn't fit into his Halloween costume. Challenge accepted."

40. Don't lose in fantasy football.

41. This is certainly a unique type of bet.

42. "My friend lost a bet 5 years ago, and his friends changed his name. He just found out it was actually accepted last week when his passport expired. He has to wait 3 years to fix it."

43. When she was a senior in high school, she bet her mom $1,500 that she wouldn't drink until she was 21. Well, she won.

44. We don't think Carson Palmer has ever won a bet in his life.

45. Dad and kid made a bet, but dad lost and had to dye his hair.

46. "We bet my grandfather he couldn't fit in my aunt's Lululemon shirt. He did."

47. "My friend Billy was challenged to beat his coworker's record of fitting 41 grapes in his mouth. Here's Billy with 42.5 grapes. Billy hates losing."

48. Michael Capuano from Massachusetts lost a Super Bowl bet.

49. He lost a bet, and now he is stuck to a road sign in Wallisville.

50. She lost a bet with her sisters.

51. "My friend didn't think narwhals were real and lost a bet because of it."

52. "My drunk friend bet me $20 he could catch an opossum. He won."

53. The ultimate punishment!

54. Turned into a fairy because she lost a bet.

55. "My friend's liberal dad called me a 'dumbass' for thinking Trump would win big league. He lost the bet."

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