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I bet you've had a bit of bad luck losing a bet at some point in your life. But the price for the bad luck you had to pay probably wasn't as big as for the people included in this list. Bored Panda has compiled a series of embarrassing moments experienced by unfortunate gamblers in the middle of their redemption, and the funny stories are both unbelievable and uncomfortable, you'll think twice about entering a wager next time.

From making a public announcement about sucking at fantasy football to transforming their hair into a pineapple, you can't help but admire people who know how to suck it up even when the worst luck strikes and accept the outcome of a funny bet. Scroll down to check out the images and upvote your favorite gambling losers.

#1

In 2001, My Parents Bet Me That If I Did Not Drink, Smoke, Or Do Drugs By 21, They Would Give Me $1500. Here I Am On My 21st Birthday Holding The Contract I Signed When I Was 8

In 2001, My Parents Bet Me That If I Did Not Drink, Smoke, Or Do Drugs By 21, They Would Give Me $1500. Here I Am On My 21st Birthday Holding The Contract I Signed When I Was 8

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Anouk
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5 years ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

That's a lot of booze, cigarettes and pot you can buy now :)

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Pamda Panda
Community Member
5 years ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

I seriously doubt his parents regret making that bet. $1,500 to keep your kid clean is a tiny, tiny price to pay.

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Monika Soffronow
Community Member
5 years ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

It would be an even better bet if the parents put aside just one, 1, ONE dollar or euro per day and put the money in a bank account where it could also gain in value. In only 10 years, there would be over 3.650 in that account. Someone who smokes / drinks / does drugs spends much more than a mere lonely dollar/euro per day on "the habit". It would be an excellent way for any parent to teach the child the real value of small amounts of money spent on something repeatedly and often. The BIG win is, of course, better health for a lifetime. Not a bad deal. Not bad at all.

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tarebear
Community Member
5 years ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

How do they know he didn't sneak a drink or toke in at a friend's house? I don't know if I'd trust that he didn't try ANYTHING...but even if he did he didn't do it enough to get caught so good for him lol

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Joe Clark
Community Member
5 years ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

How does this fit with the title “They Probably Wish They Hadn’t”?

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Ashley
Community Member
5 years ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

The parents probably wish they haven't had because now they have to give him $1500

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Cami Ereth
Community Member
5 years ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

So many cool things he can do with that 1) buy a computer 2) a down on a new-used car 3) classes (even for fun) 4) plane ticket to the beach/mountains... Anything he is interested in. And, unlike when you are drunk/high/fighting lung cancer, he can enjoy what he chooses with no down-side.

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Meowton Mewsk
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5 years ago

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If you think you can’t enjoy a beautiful nature scene or a pottery class or something while high on marijuana, a cookout with friends and beer, or new tv and movies with either, etc, you have a lot to learn and a lot to unlearn.

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DancingToMyself
Community Member
5 years ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Exactly! My interests were sooo different from my "friends". I had no time, nor did I had to party in such ways.

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varwenea
Community Member
5 years ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

There should have been a triple or nothing to age 23, covering him through getting a bachelor's degree. I think that would be good to set him on good habits.

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PBMc
Community Member
5 years ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Why is this a "bet" they wished they didn't make? Seems more like it was meant as an incentive to prevent drinking, smoking, and drugs

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Cindy Bryson
Community Member
5 years ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Very proud of you! You look like an awesome kid! Way to go. I'm sure you will use or invest the money wisely!

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jknbt jknbt
Community Member
5 years ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

yeah, right, I heard about you at summer camp when you were 13!

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SykesDaMan
Community Member
5 years ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Now you have 1500$ to spend on booze, tobacco and whatever drugs you like! :)

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alicia
Community Member
2 years ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

How would they know that though unless they literally kept him locked up lol

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Id row
Community Member
4 years ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

How do you enforce this? Drug test the kid every three days?

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Bored Fox
Community Member
5 years ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Now I feel sad that I did not make a bet like that. I waited until I was an adult to try those things first time.

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noitall man
Community Member
5 years ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

I raised my daughter simply to have respect for herself rather than bribe her...

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Paul O'Connor
Community Member
5 years ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

I also avoided all of this until I was 21. After that I soon discovered the error of my ways and went right off the rails LOL!

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minerva15
Community Member
5 years ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Good on him for being healthy. Smoking and drugs are horrible for your health. Alcohol is OK in responsible amounts. With all the crazy teens nowadays, I'm proud of him. I hope he realized it as well.

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.gas.
Community Member
5 years ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

That's less than $100 a year. For that type of commitment, I feel the payout should have been larger.

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Dan Carter
Community Member
5 years ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Thanks, but no thanks. If you can't make $1500 on your own at 21, you're doing it wrong.

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Sandra Hill
Community Member
5 years ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

I drew up a contract like that for my oldest daughter stating she would not tattoo or pierce her body without permission until she was 18.

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Victor Manteca Hierro
Community Member
5 years ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

My parents bet me that if I DID drink, smoke or do drugs before 18, they would beat the sh*t out of me. Word contract.

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Bobbi Newell
Community Member
5 years ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

My parents didn't bet me, but they DID make a bargain: If I avoided smoking till age 21, they'd buy me the car of my choice. I had so much fun in my black '88 convertible Mustang 5.0 GT!

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Robert Wade
Community Member
5 years ago

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AND as a legal contract it is actually just a piece of paper.. You were not of legal age to sign a contract... If they don't pay, you can't make them.

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Charlotte Brine
Community Member
5 years ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

luckily judging from the money on the table and the fact that most parents aren't s****y enough to present him with that kind of excuse i'd say the legality wasn't exactly a necessity in this circumstance

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JessyJoy
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5 years ago

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I really don't think it's worth missing out on drunken times with your friends

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Calypso poet
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5 years ago

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Did he also promise no sex? Because that face and T-shirt screams virgin.

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Calypso poet
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5 years ago

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No thanks. I would rather have had the fun.

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Phillip Moderow
Community Member
5 years ago

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Good thing "womanizing" wasn't on the list. Now you can share it with all your children which comes to what -- ? $52 each ? Think "A Clockwork Orange". Seriously, good for you.

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James Floyd
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5 years ago

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I'd have violated it. I had FUN in Uni and make $1500 in no time

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r3dd3v1lL
Community Member
5 years ago

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Smoking and drugs I agree on, but what's wrong with having a beer or a glass of wine every now and then? Not to mention unprotected sex is far more dangerours than drinking a couple of beers.

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Giovanni
Community Member
5 years ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

In the States the legal drinking age is 21, so the contract was more about respecting the law than potential health problems.

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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

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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diz_1 avatar
Laugh Fan
Community Member
5 years ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

He knew he was going to 'lose'! Just a fun way to get the children reading more.

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#3

One Month Ago I Challenged One Of My Campers Who Had Just Been Diagnosed With Dyslexia. I Told Her That If She Could Read 10 Chapter Books In The Month Of July, I Would Let Her Choose Any Color She Wanted To Dye My Hair. Well She Finished Her Challenge And Alas I Now Have Pink Hair

One Month Ago I Challenged One Of My Campers Who Had Just Been Diagnosed With Dyslexia. I Told Her That If She Could Read 10 Chapter Books In The Month Of July, I Would Let Her Choose Any Color She Wanted To Dye My Hair. Well She Finished Her Challenge And Alas I Now Have Pink Hair

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#4

I Won A Bet With The Library At My University Forcing Them To Hang A Portrait Of Me Till I Graduate. Here's The Photo I Submitted

I Won A Bet With The Library At My University Forcing Them To Hang A Portrait Of Me Till I Graduate. Here's The Photo I Submitted

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#5

I Work With Patients In Rehab. 2 Months Ago I Made A Bet With A Patient I Would Shave If We Could Get Him To Reach A Certain Goal. Today, He Did It. Tomorrow He Gets Baby Me

I Work With Patients In Rehab. 2 Months Ago I Made A Bet With A Patient I Would Shave If We Could Get Him To Reach A Certain Goal. Today, He Did It. Tomorrow He Gets Baby Me

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#8

A Swedish Principal Made A Bet With A Student; If The Student Could Make It Through 9th Grade The Principal Would Dye His Hair Pink. Last Week The 61-Year-Old Principal Delivered!

A Swedish Principal Made A Bet With A Student; If The Student Could Make It Through 9th Grade The Principal Would Dye His Hair Pink. Last Week The 61-Year-Old Principal Delivered!

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#9

When You Talk A Big Game But Your Sister Beats You In The Match And The Rematch

When You Talk A Big Game But Your Sister Beats You In The Match And The Rematch

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#10

“Bet We Can Beat You At Hide And Seek Uncle David!” Bet You F**kin’ Can’t

“Bet We Can Beat You At Hide And Seek Uncle David!” Bet You F**kin’ Can’t

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#11

Lost A Bet With My Cousin, This Is The Result

Lost A Bet With My Cousin, This Is The Result

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#12

I Bet The Girls Upstairs That I Could Fit Into Any Clothing That They Could. I Won

I Bet The Girls Upstairs That I Could Fit Into Any Clothing That They Could. I Won

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#13

This 86-Year-Old Challenged Me To A Pole Dancing Contest While At Happy Hour, He Won

This 86-Year-Old Challenged Me To A Pole Dancing Contest While At Happy Hour, He Won

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diz_1 avatar
Laugh Fan
Community Member
5 years ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Crikey - I'm not that able at several decades younger. Good for you!

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#14

Told My Girlfriend It Was Impossible To Stand A Coin On Its Side

Told My Girlfriend It Was Impossible To Stand A Coin On Its Side

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#15

Was Bet That I Couldn't Balance A Cue Ball On Three Pool Cues. Nobody Played Pool The Rest Of The Night

Was Bet That I Couldn't Balance A Cue Ball On Three Pool Cues. Nobody Played Pool The Rest Of The Night

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#16

My Husband Bet Me I Couldn't Shave His Foot Without Him Waking Up. This Is What He Woke Up To This Morning

My Husband Bet Me I Couldn't Shave His Foot Without Him Waking Up. This Is What He Woke Up To This Morning

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#17

Never Challenge Your Child To Do Something Unless You Are Prepared For Them To Succeed

Never Challenge Your Child To Do Something Unless You Are Prepared For Them To Succeed

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diz_1 avatar
Laugh Fan
Community Member
5 years ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Looks like it took the bird a few seconds to realise what had happened. Bottom photo it's thinking 'what the actual f happened here?'

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#18

Friend Lost A Bet. Here's Her Senior Picture

Friend Lost A Bet. Here's Her Senior Picture

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#19

He Bet Me That He Could Touch His Head To The Ceiling

He Bet Me That He Could Touch His Head To The Ceiling

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#20

My Teammate Is A 5'6" Gymnast. She Bet Us She Could Completely Fit In Her Locker. She Won

My Teammate Is A 5'6" Gymnast. She Bet Us She Could Completely Fit In Her Locker. She Won

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#21

Lost A Bet And Had To Go Through Airport Security Dressed As A Dinosaur (TSA Said I Looked Cute)

Lost A Bet And Had To Go Through Airport Security Dressed As A Dinosaur (TSA Said I Looked Cute)

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#23

I Lost A Bet With My Girlfriend. Here's Our Costumes This Year

I Lost A Bet With My Girlfriend. Here's Our Costumes This Year

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#24

Won A Bet Against My Boss Nearly A Year Ago. Came Into Work To See That He Finally Paid Me. In Pennies

Won A Bet Against My Boss Nearly A Year Ago. Came Into Work To See That He Finally Paid Me. In Pennies

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#25

My Friend Had A Bet With My History Teacher. He Lost

My Friend Had A Bet With My History Teacher. He Lost

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#27

Boss And Coworker Made A Weight Loss Bet - Loser Had To Cross Dress. That Is His Real Hair Though

Boss And Coworker Made A Weight Loss Bet - Loser Had To Cross Dress. That Is His Real Hair Though

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#28

My Band Director Lost A Bet And Had To Wear A Banana Suit All Day

My Band Director Lost A Bet And Had To Wear A Banana Suit All Day

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Miss Cris
Community Member
5 years ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

I'd ike to be in a concert where musicians were dressed in that way, it'd be nice :)

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#29

My Histroy 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

My Histroy 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

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diz_1 avatar
Laugh Fan
Community Member
5 years ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

He looks fine with his head shaved and is clearly proud of his student.

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#30

So My Friend Got Drunk And Bet Me He Could Fit An Entire Box Of Straws In His Mouth. Did Not Disappoint

So My Friend Got Drunk And Bet Me He Could Fit An Entire Box Of Straws In His Mouth. Did Not Disappoint

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#31

When Your Dad Bets $50 That The "Physics In A Nutshell" Ruler/Hammer Post Is Impossible

When Your Dad Bets $50 That The "Physics In A Nutshell" Ruler/Hammer Post Is Impossible

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#32

Lost A Bet, Have To Wear This Bad Boy From Christmas Eve To New Years Eve

Lost A Bet, Have To Wear This Bad Boy From Christmas Eve To New Years Eve

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#33

Bet A Friend He Would Not Play Dodgeball In A Tu-Tu. He Won

Bet A Friend He Would Not Play Dodgeball In A Tu-Tu. He Won

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#35

Well, My Brother Lost A Bet And Had To Go On A First Date Dressed Like This

Well, My Brother Lost A Bet And Had To Go On A First Date Dressed Like This

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Note: this post originally had 56 images. It’s been shortened to the top 35 images based on user votes.