There’s a time and place for a wager between friends, to be sure, but folks, be careful what you put up for stakes. If you can’t afford to pay up, don’t make that bet. And most importantly, know who you’re betting against, because sometimes, even when you win, you still manage to lose.
Just check these folks out and see for yourself.
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“My husband bet me I couldn’t shave his foot without him waking up. This is what he woke up to this morning.”
So either he’s a heavy sleeper or she’s a confirmed light touch with a blade and nail polish. Whichever is the case, he’ll probably forgo sandals for a while.
“When you talk a BIG game but your sister beats you in the match and the rematch.”
The good news for this lad is that when life teaches you tough lessons, you’re less likely to forget them down the road.
“I challenged my friend, who owns an iPhone, to a boot race against my HTC One. I was able to take a picture of him while his phone was still booting.”
For such an inconsequential thing, the look on that guy’s face is priceless. That’s a pic that will last forever, long after both phones are obsolete.
This principal challenged the kids at his school to read a combined 1,000 minutes, and they clearly made good on that challenge.
Their reward? To get to push him down the hall on a tricycle, with him wearing mismatched clothes inside out.
Pretty inspiring, actually!
“This 86 year old man challenged me to a pole dancing contest while at happy hour, he won.”
And he’s already got me beat as well — not bad at all, the guy still has moves, and plenty of core strength!
“Friend bet me $100.00 that a car radiator could not be incorporated into a computer…$517.82 later, I got my $100.00!”
A victory in principle, but not exactly the wisest financial decision. I guess it established the cost of such a venture for the rest of us, too.
When this person lost a bet, they put their very identity on the line — and lost.
![Image credit: Reddit | [deleted]](https://static.diply.com/vY3oNse8yKheXxnUMIax.jpg)
He allowed his friends to officially change his name, but didn’t find out it had been accepted until his passport expired .
What a nice surprise!
“My friend had a bet with my history teacher. He lost.”
Can’t think of a more appropriate way to lose a bet to a history teacher, to be honest.
Betting against Canada in hockey is risky.
And this guy found out the hard way when he bet his roommate the U.S. would win. Hope he didn’t have to run far!
One thing you can say about sports fans, however: they pay up.
Like this Dallas Cowboys fan, who ended up out in traffic after losing a bet with a Green Bay Packers fan.
Hairlines are high stakes for bets between friends, and this guy lost his hair privileges for a month.
Not sure where they go from here, but that’s a fantastic ‘do to celebrate your win.
And then there’s this guy, who had to surrender his locks to his cousin after losing a bet, and ended up with a tropical style.
I don’t know, this guy actually kind of pulls off the pineapple noggin.
“Bet we can beat you at hide and seek, Uncle David!”
Or maybe not. Heck, can you spot Uncle David’s hiding spot? These kids will be at it until bed time — which is a pretty ingenious babysitting strategy.
Is winning a bet against a welder really winning?
I mean, this welder did technically pay up, forking over a bottle of booze, but not before making it extremely difficult to access.
“My team mate is a 5’6″ gymnast. She bet us she could completely fit in her locker — she won.”
I’m not sure exactly what she won by that display of contortion, but it’s seriously impressive all the same.
This guy’s parents lined him up for success with a simple bet.
“In 2001, my parents bet me that if I did not drink, smoke, or do drugs by 21, they would give me $1500,” he wrote. “Here I am on my 21st birthday holding the contract I signed when I was 8.”
That’s a well earned mess of cash that I suspect his folks were more than happy to fork over.
Be careful what you bet for, especially cold, hard cash.
“Won a bet against my boss nearly a year ago,” wrote the uploader. “Came into work to see that he finally paid me…in pennies.”
“Lost a bet, have to wear this bad boy from xmas eve to new year’s eve.”
There are ugly Christmas sweaters, and then there are downright uncomfortable Christmas sweaters. I can feel this itching through the screen.
I’m surprised they lasted an hour.
Imagine the whispered conversations among the employees as they tried to put off having that awkward exchange.
How long before they realized that she wasn’t planning to move on her own?
“My band director lost a bet and had to wear a banana suit all day!”
And he looks about as thrilled about it as anyone who spends the day surrounded by teenagers would be.
He lost a bet against Air Asia chief executive Tony Fernandes about whose team would win in the Formula 1 Grand Prix. So he had to dress up as a female flight attendant.
Mario Lopez also proved that losing a bet is worse when you’re famous.
Sure, most people will notice the nearly-naked guy who lost a Superbowl bet, but they don’t all make international news.
“Had to spend the day as Link. To make matters worse I fell asleep in bio, and then people started texting me pictures of myself to wake me up.”
If those texts weren’t “HEY LISTEN!!” every five seconds, then those people are doing it wrong.
While I mostly think guys having to wear a dress is a weak punishment for losing, this one’s great.
Something about it being a wedding dress complete with veil really makes it work. Especially considering the look on his face.
Sometimes it’s just fun money.
That’s a pretty well-folded money shirt. I’d definitely keep it folded up like that just to see the look on the barista’s face when I paid for my coffee with it.
“Was bet that I couldn’t balance a cue ball on three pool cues. Nobody played pool the rest of the night.”
This actually isn’t hard, but it blows some people’s minds when it works. I get not wanting to be the guy that takes it down just to play a game.
Placing any sort of bet while drunk is a mistake.
This guy is just really lucky that whoever won allowed him to keep both his eyebrows when everything else was shaved.
“Never challenge your child to do something unless you are prepared for them to succeed.”
The parents probably hoped that the bet would result in the kid tiring himself out. Instead, they’re desperately trying to remember when his last round of vaccines was.
“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.”
Some bets are good ones.
Also, baby him looks so much younger!
“I lost a bet and let my sister cut my hair. This is the face of instant regret.”
He doesn’t say whether or not he agreed to leave it that way for a specific period of time. If not, I’d put on a hat and get thee to a barber shop.
Bad haircuts are a classic thing to bet with.
Bonus points to this guy for agreeing to do this on his birthday or all days.
But hey, I hear the mullet is making a comeback.
Never try to say something is impossible.
“Told my girlfriend it was impossible to stand a coin on its side.”
Clearly, it’s not.
Would it be awkward to have to wear this to school? Yep.
But, admittedly, it looks pretty comfy. The cushioned head would be perfect for napping in class.
Again, this seems like the kind of bet where you secretly win by losing.
Seriously, though, the Diply office is often freezing and I’d definitely wear something like this to stay warm and comfy.
I hope this guy likes Ryan Gosling half as much as his shirt says he does.
I mean, who doesn’t like him? My love goes all the way back to Breaker High but he’ll always be Young Hercules in my heart.
This guy had to go through airport security in a dinosaur outfit after he lost a bet.
Glad he can smile about it — I would think it would be pretty uncomfortable, even considering all the strange things the TSA sees every day.
“My dad recently lost a lot of weight. I bet him he couldn’t fit in my skinny jeans.”
Good job, Dad!
She must be a lot taller than him, judging by the amount of hem covering his feet.
“I bet the girls upstairs that I could fit into any clothing that they could. I won.”
This is actually pretty awesome in its own way — and makes me wonder if it inspired a change in wardrobe for the girls upstairs.
Okay, standing ovation for this dedication to the bet.
“I lost a bet to my boyfriend, Ethan. As a result, I had to make an original rap video about how he is just the best, and post it online for the world to see. I hope you enjoy watching it half as much as I enjoyed making it.”
