People Who Took A Gamble On A Bet And Obviously Ended Up In The Loser’s Bracket

Placing a bet is a risk. In fact, you probably lost a bet at some point in your life. In high school, I bet my buddy the Chicago Blackhawks were going to win another Stanley Cup, but he didn’t think so. By the time the Hawks won another cup in 2013, my buddy had to cut my lawn in a Jonathan Toews t-shirt, and I watched in a lawn chair.

See, it’s the price and sacrifice you’re willing to pay, but for some people on this list, they regret making a bet. You can’t help but admire the people who know how to suck it up even if they’re a poor sport. The next time you want to place a bet, be mindful of the aftermath.

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

Photo Credit: haonconstrictor/Reddit
Photo Credit: haonconstrictor/Reddit

He’s got moves like Jager. I bet it was hard for him to get tips because his shorts are pulled up way too far.

This guy might be old, but he knows how to make rain better than a stripper. I don’t think he’ll be dancing around poles full-time anytime soon. It’s a one-and-done situation.

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

Photo Credit: @jennieleeknight/Instagram
Photo Credit: @jennieleeknight/Instagram

You know what? This will probably be one of the most useful moments in his life. It will profoundly shape the person he becomes, and it’s a harsh lesson in losing.

He’s not a happy camper, but he’s strong and confident for embracing the embarrassment of losing to his sister.

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!

Photo Credit: NAKED_SWEDISH_CHEF/Reddit
Photo Credit: NAKED_SWEDISH_CHEF/Reddit

Pink hair is cool, especially if you’re a principal. That is outstanding and a big sacrifice to make.

A cool principal like this is someone who cares so much about his students. It looks great on him, but I kind of wish my principal was just as fun and awesome as this guy is. The next one ahead is for any music students who want to get back at their band director. Trust me, you’ll go bananas.

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

Photo Credit: Gultrum/Reddit
Photo Credit: Gultrum/Reddit

That’s a lot of booze, cigarettes, and pot you can buy now! Unfortunately, your parents didn’t tell you how much $1,500 would be worth 13 years down the road.

However, he stuck to his long commitment, which probably was difficult as he got older. Now, he can finally treat himself to whatever he desires most.

You Win Some, You Lose Some

Photo Credit: @soychingon23/Twitter
Photo Credit: @soychingon23/Twitter

Haha, sucker! However, with his acquired skills, he made himself into a trophy husband.

Think about it, those are skills he’s going to need when he gets to college, and the day he lives on his own. You have to start them young or else you’re going to have very lazy kids.

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

Photo Credit: evanhimes0/Reddit
Photo Credit: evanhimes0/Reddit

The band director is like “Okay, you made me dress like this, so let’s play some Hollaback Girl.” I’d like to be in attendance at that concert, especially if this guy is going to be dressed in full potassium.

If he loses another bet, I hope he dresses up like a bee. That way, the band can play “Flight of the Bumblebee.” Despite losing, the principal of an elementary school found a way to get his students to read more. Find out what he did shortly!

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

Photo Credit: dropkickderby/Reddit
Photo Credit: dropkickderby/Reddit

Kudos, Uncle David! Now we know who the fun uncle in the family is. He’s got some mad hide and go seek skills.

At the same time, the little girl in the hallway would be ideal for a horror movie poster. Sometimes, you refuse to grow up, but in Uncle David’s case, he knows how to be hilarious.

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

Photo Credit: dillwillhill/Reddit
Photo Credit: dillwillhill/Reddit

Come on now, that dress should be floor length! In this case, you’re wasting your time by saying yes to the dress.

It’s a like mix between Belle and Tinkerbell but I’m pretty sure that’s a child size dress. The only thing the guy in the dress is missing is a wig.

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

Photo Credit: Cooter_McDoogletron/Reddit
Photo Credit: Cooter_McDoogletron/Reddit

Despite knowing he was going to lose, that’s a fun way to get the children to read more.

Also, the children seem so incredibly happy, especially with the principal wearing unmatching clothes inside out. It’s amazing that this guy knows how to stand by their words. Well done! One student attempted to defy the odds by getting a high grade on his test. Did he do it? You’re about to find out soon.

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

Photo Credit: Drewdledoo/Reddit
Photo Credit: Drewdledoo/Reddit

Straws are a no-no these days, but on the bright side, at least he can still breathe. Sure, this is a very big mistake to make, but we learn from them regardless of how stupid we are.

Now he knows what a five-year-old feels like when they have asthma.

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

Photo Credit: kauffj/Reddit
Photo Credit: kauffj/Reddit

Well, there’s something about this guy. He’s just one of a kind. If I got called cute by the TSA, I’d start flirting.

I don’t care if I’m not from Chicago — if you’re cute and seem nice, I’ll gladly strike up a conversation with you. If you play your cards right, you might get a hot date out of it.

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

Photo Credit: KingTurboXXIII/Reddit
Photo Credit: KingTurboXXIII/Reddit

Honestly, he looks fine with his head shaved. Most of all, he’s clearly proud of his student, like a good teacher should.

He kind of looks like Chester Bennington, which is pretty eerie too. But, the fact that the teacher is taking this bet in stride makes you respect him even more. What happens when you suck at fantasy football? Just ahead, one guy had to swallow his pride like it was a walk of shame.

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

Photo Credit: Reddit
Photo Credit: Reddit

It might be too risky to ask if there was a second date. Personally, I would like to know because Futurama is awesome.

It would be epic if his date showed up as Leela, but I highly doubt that happened. Here’s hoping this guy doesn’t have to resort to apps like Tinder or Bumble.

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

Photo Credit: emitzelfeld/Reddit
Photo Credit: emitzelfeld/Reddit

It’s one of those things where it might not look hard to do, but it really is. It’s nice that engineering school paid off for once.

However, let me ask you this. Who here wished they hadn’t made this bet? Even the losers should have been delighted by this.

Don’t Lose Your Fantasy Football League

Photo Credit: ggravelle/Reddit
Photo Credit: ggravelle/Reddit

Whether it’s fantasy football, basketball, baseball, or hockey, every league has a loser. It seems to be a recurring theme that whoever finishes last has to pay the ultimate price of punishment.

But, this is a learning opportunity to not suck next year because you’ll want a shot of redemption to silence your friends. The next one ahead is similar to this, but it’s really dangerous. But, drivers could finally yield for once in their lives.

Yeah… I Lost A Bet With My Sisters

Photo Credit: @Allen1Darrian/Twitter
Photo Credit: @Allen1Darrian/Twitter

Okay, maybe she did a hot take on the new season of Orange is the New Black. Of course, she was completely wrong, so now she has to wear this tutu.

Maybe next time she should watch the show before making bad predictions, especially if it doesn’t make sense.

This Poor Guy Bet His Roommate America Would Beat Canada In Hockey

Photo Credit: dcdcd101/Reddit
Photo Credit: dcdcd101/Reddit

American’s are weeping over what happened in the gold medal game in 2010. As a Canadian, I like this because it’s an example of how cold winters in the great white north are.

Honestly, though, I get that you have confidence in your country, but Canada will always be the best at hockey.

This Guy Lost A Bet And Now Is Stuck To The Yield Sign On Wallisville

Photo Credit: Elizabeth Oliveria/Facebook
Photo Credit: Elizabeth Oliveria/Facebook

Uh, okay. It’s not like this isn’t dangerous or anything. He’ll be a distraction at such a busy location! It’s mean and I guess cars will actually yield for once, especially if you look like an idiot.

Oh well, that’s what you get for making a bet believing LeBron James was going to sign with the Philadelphia 76ers.

We Had A Bet About Our Baby’s Gender… My Husband Lost

Photo Credit: the_great_tate/Reddit
Photo Credit: the_great_tate/Reddit

Give this man a standing ovation. This man can have a sense of humor even when he loses. I could imagine what the wife would have to wear if the baby was a boy.

Probably just some of her husband’s clothes, but equipped with a lawn chair and a cold one to go with it.

She Lost A Bet

Photo Credit: Heather Walechka/Reddit
Photo Credit: Heather Walechka/Reddit

Yikes, that’s the sight of a drunken butterfly. Did she ever learn not to put money down on the Cleveland Browns?

Sure, they have a new quarterback, but they went 0-16 in 2017. At least it wasn’t something worse like having to do the naked mile.