Proposal Fails to Make You Cringe
A proposal is one of the most important moments in a couple’s history. The guy usually tries to do something meaningful and gets a pretty ring in an unforgettable setting.
However, sometimes, proposals fail … epically. The ring is lost, people get sick, she says no or something even worse happens. It turns out there are a lot of things that can turn the best moment of your life into a nightmare.
Up Up And Away
A man surprised his partner with a heart-shaped balloon. Then he walked her over to a preselected spot in a grassy field and dropped to his knee. Feeling shocked, she brought her hands to her face and let go of the balloon.
The man then panicked and ran off chasing the balloon. Why? He had tied the ring to the end of the balloon string! The balloon continued to fly off with the man in pursuit. The woman couldn’t believe it, asking, “Why did you tie the ring to the balloon?”
Halftime Half Court Fail
On Valentine’s Day, a man got down on his knee at half court. Everything was shown on the jumbotron, and the crowd was cheering. Somehow, though, the woman’s face was not right. She didn’t look happy — she looked concerned.
She clearly mouthed, “I can’t do this” repeatedly and then ran away. The crowd was collectively in shock while the guy sheepishly walked away in the opposite direction as the mascot consoled him. If you’re going to propose in a public place, please make sure she is going to say yes.
Interrupted
In this story, the proposal went off without a hitch. The man proposed next to the same park bench where they first met. Then they decided to film a video to document the experience for the bride-to-be’s mother. The woman excitedly told the camera that she was engaged and showed the ring off, but then she was interrupted.
Two guys nearby got into a screaming match about dog-doo, and the fight escalated. The one guy picked up the poop and smeared it on the other guy’s face! The men ran away, one chasing after the other. At least it was memorable!
Should’ve Left the Dog at Home
It was a beautiful fall day. A man was going on a hike with his girlfriend and dog. He set up the camera to record the special moment and stepped into the frame to ask the question. He dropped to his knee, and the woman started to freak out from excitement.
She let go of the dog’s leash. Just as the guy was about to ask the big question, the wandering dog knocked over the camera and the screen went dark. So much for capturing the special moment.
White Castle Proposal Fail
While a White Castle restaurant is probably not the ideal place to propose, the couple seemed to have a shared sense of humor, so maybe it was okay? However, just as the guy began to say that they had been together for a few years now, the guy at the next table called the entire restaurant to attention.
Then that same guy dropped to his knee and proposed! The woman said yes and everyone in the restaurant was excited for them, except for the first guy who couldn’t believe someone else swooped in on the situation.
Just Smile and Wave
One woman was dating a guy for a while before she realized they had different opinions on family life. She was an independent woman with a good job, but he was a close-minded type who thought a woman’s place was in the kitchen and at home taking care of the kids.
They were out for dinner, and she was just about to break up with him when he proposed. Now everyone in the restaurant was looking at them. Not wanting to make a scene, she nodded but whispered to him no, and they shared an awkward hug.
Waterfall Mistake
He had the perfect romantic setting. Someone was filming the magical moment and everyone was excited. In the middle of a beautiful waterfall on a rock, a man got down on his knee and asked her to marry him. She said yes, and they looked so happy. He held out the ring, but then, oh no!
The ring slipped out of his fingers, and into the water it went. The moment of joy was replaced by horror as the ring disappeared into the water. The ring was never recovered, but at least she said yes, right?
Stalker Alert
One woman described a situation where a guy was in love with her but she clearly did not feel the same way. The guy first emailed her a proposal — really, bro? Email? — and then tried again over the phone.
Shockingly, she said no both times. Then, six years later, the same guy proposed again! This time it was in person, but of course she still said no. The third time was not the charm for this fellow.
Shopping Mall Proposal Fail
A guy decideD to propose in the place where he and his significant other first met. Cute, right? Well, maybe, if they hadn’t met only three months ago in a shopping mall. He had musicians playing and began to profess his love over a microphone speaker system.
He then started using the most cheesy lines and calling her cutie pie and every other cringy thing in the book. Then he began to ask if she would “make [him] the happiest man … ,” but by then, she’d had enough and grabbed the musician’s ukelele and clocked him in the head before storming off. That’s one way to send a message.
Party Gone Sour
It’s a huge party. A friend is belting out a love song for the intended bride. Then the man took the microphone and started professing his love to her. However, the woman just stood there, clearly unimpressed by any of it. She had a look on her face like she couldn’t believe he thought this would work.
The man clearly did not understand body language and continued to move forward with his plan. She just stood there, unimpressed and shaking her head until the camera cut off. This was a particularly bad situation, since he probably ruined the party with the failed proposal.
In Sickness and in Health
A man got the idea to propose to his girlfriend while taking a romantic flight on a small private plane over the town where she grew up. He even made a giant sign that was set up to be read from the air, “Marry me?”
But what the man didn’t account for motion sickness. No sooner had he pointed out the sign and presented his significant other with the ring than he threw up. Yikes! But the woman remained calm and rubbed his back, showing that she really would stay with him in sickness and in health.
Too Soon?
A girl was in her sophomore year of high school and had been dating this boy for two months. Apparently, however, that was all the time that he needed to decide he wanted to propose marriage. He asked his mom for his grandmother’s ring so he could propose.
In an amazing failure of parental guidance, his mother agreed and gave her son the ring! He then proposed to the shocked girl, who of course said no. The girl did say that it was a beautiful ring, but the boy and his family must have been crazy to think that was a good idea.
Not Even Neil Diamond Could Save This Proposal
Played before the bottom of the eighth inning at every Red Sox home game is Neil Diamond’s hit song, Sweet Caroline. During one particular match, there was supposed to be a marriage proposal on the jumbotron. But when the camera lands on the couple, they were instead arguing.
The cameraman cut away from the scene, and the crowd groaned. It’s not clear what happened here — maybe the cameraman got the wrong information about where the real couple was seated? — but it’s not a promising sign.
Photographer Fail
A photographer was hired to take pictures of a proposal at sunrise. He hiked up to the pre-selected spot and waited. The couple showed up a little late, but that was fine. He snapped a bunch of pictures of them from a distance and then sent a text to his client saying congratulations.
However, the reply he received was one of confusion, because according to the couple, they never showed up. It turned out he took photos of the wrong couple! The photographer then used social media to locate the couple in the photos and gave them the photos free of charge.
Lost And Found
Keeping the ring safe until the perfect moment is crucial. One man understood this and prepared accordingly. He planned on proposing on the beach at sunset, so he kept the ring on a chain around his neck for safekeeping. Finally, the moment came. He dropped to his knee and reached for the chain to get the ring.
Of course, the necklace snapped off and the ring fell into the sand. The couple searched for a long time before eventually renting a metal detector. They found the ring a few minutes later and all was well. Luckily, this one was only a temporary fail.
Cheating Should Lead to a Proposal, Right?
One woman was in a relationship where she did all of the work, helped her partner to pay off his debt and kept the apartment clean. She was the perfect girlfriend. His response? He cheated on her, so they broke up.
They wanted to end things on good terms, though, so they made plans to meet up at a restaurant to talk. Then in an attempt to get her back, the man decided to propose. She said no, and he reacted by crying and singing Bruno Mars songs. Sounds about right.
Take Me Out to the Ball Game, Just Don’t Bring a Ring
This proposal was quite elaborate, not your run-of-the-mill jumbotron proposal type situation. The guy had the grounds crew do an entire choreographed dance on the field to Bruno Mars’ Marry You. Then the guys held up signs that together read, “Will you marry me?”
The prospective groom in the stands dropped on his knee and held up the ring to his future bride, but the woman shook her head, leaned in and told him something quietly. Then she grabbed her purse and walked away. That’s gotta hurt.
The Roommate Meant Well
A college sophomore was dating a guy for less than a month. She came back to her house to find him in her room on his knee with little heart-shaped papers all over the floor.
Apparently, he had convinced her roommate to let him in. The woman then pretended she didn’t understand what was going on and said she had to go to the bathroom. She then called her roommate from the bathroom and told her that since she let him in, she had to kick him out. Ouch!
Workshop Woes
A couple met in a friendship bracelet workshop, so the would-be groom thought it would be cute to propose in the same place. He got a box with letter beads spelling out the words “Will you marry me?” on it. Sweet idea right?
Well, when the woman was presented with the beads, she wasn’t ready to say yes, but she didn’t want to cause a scene. So she just knocked around and messed up the beads so no one would know what had happened. However, her emotions got the best of her and she started sobbing in the middle of the class anyway.
Don’t Propose When You Are Broken Up
A breakup is a pretty obvious sign that a couple isn’t meant to be. After one woman broke up with her boyfriend, however, he secretly contacted her dad. Then the ex asked her to meet him at a cathedral. She was hungover and tired, but for whatever reason, she agreed, not catching on to what was going to happen.
At the cathedral, her ex proposed with a necklace, because of course he did. She of course rejected him. Perhaps he thought he could get her back with a proposal. Either way, this is why Ross Geller from Friends is a poor romance role model.
Two Proposals, Same Answer
A woman just found out she was pregnant. She was hanging out with her boyfriend at the time when he casually asked, “So, do you wanna, like, go get married before you tell your mom you’re pregnant?” She responded by laughing. She broke up with him a couple of months later.
But a few weeks after the baby was born, the guy tried again, this time, with a ring. She politely declined. He responded by saying “April Fools!” Maybe it was an attempt to preserve his dignity if she said no?
I Thought We Said We Weren’t Ready
A couple had just had a discussion about marriage two weeks before, and they’d both agreed they weren’t ready — or at least, that’s what the woman thought. Then, during the captain’s dinner on a cruise ship, the man decided to propose in front of everybody.
She said yes so as not to embarrass him, but when they returned to their room she said no. They then got into a huge fight that caused so much ruckus that security was called to their room. They had to be separated for the entire evening because the neighbors complained so much.
The Worst Executed Proposal Ever
A woman suspected that her boyfriend was cheating on her. She eventually found out that he was talking to another woman online. She then confronted him and prepared to break up with him. To stop her, he had the bright idea to propose to her.
She wasn’t feeling it. “Next time you propose to a girl,” she yelled, “You better be on one knee, have a ring in your hand and you sure-as-hell need to pronounce her last name right!” At least the guy knows how to propose for real now.
Penpal Wannabe
A man planned on joining the military, but he wasn’t married, and he wanted someone to write letters to. To solve this fairly benign problem, he took the entirely reasonable step of proposing to his ex-girlfriend over IM. He explained to her that he wanted someone to write to when he was overseas. Her response? “No, that’s stupid.”
It turns out the guy was also seeing another ex at the same time. Then the guy that ex, and she hasn’t seen him since. Looks like the first ex dodged a bullet. Hopefully he did the same while in the military.
Health Insurance Scam
Two people had only been dating for about two months when the guy decided to pop the question. She said no, and he cried his eyes out. Then, a couple of hours later, he proposed again. She still responded no, saying that it was just too soon.
But the woman’s mom was pressuring her, so she finally relented and said yes when he proposed the third time. He then had three surgeries that he had been putting off because he couldn’t afford them. With his new wife’s health insurance, however, he suddenly could. Their marriage only lasted eight months.
Short on Cash and Good Ideas
A couple had only been together for a month when the guy decided to propose. They took a seaplane flight for her birthday, but he was short $75, so she had to help pay. While in the air, he pulled out a ring. He then began recording her and told her to explain what was going on so they could play a video of it at their wedding.
She told him to put the camera down. After they landed, she gave him back the ring. Considering they were only together for a month, that was probably the right choice. Some people are just too eager.
Things Go From Bad to Worse
One man went above and beyond with his plans to get a wife. He hired a crane so that he could be raised up to the would-be bride’s window to propose. Super sweet, right? Well, it would have been sweet if the crane hadn’t malfunctioned and swung into the side of the building and damaged a neighbor’s apartment.
The man made it to safety, but then they had to call in a bigger crane to remove the smaller crane. That ordeal turned into more damage to six other apartment units. Sometimes it’s not the thought that counts, but the collateral damage that matters most.
The Fake Fail
A couple was on a fishing trip when he asked her to film him performing a trick with the dogs. Instead, he dropped to his knee and proposed, but then he stumbled and accidentally dropped the ring into the murky water.
The girl freaked out and the guy exclaimed he didn’t even have insurance on the ring. But then he told her to keep filming and pulled out the “real” ring. She laughed in disbelief but said yes. Now that is a successful fail.
Backup Fiance
A girl had gone on a few group dates with this guy (he was 18 and she was 16). They were having fun, but it was nothing serious. Then he proposed to her out of the blue. She was absolutely shocked and said no. He spent the rest of the date trying to convince her to say yes.
The next day, the girl’s friend asked her if she’d heard that the very same guy was getting married. Apparently, he had a back-up potential fiance and proposed to her when the first girl said no.
Should’ve Been a Yes, Right?
Two people had been dating for six years, so the man thought it was time to propose. They’d talked about marriage and everything seemed to be good. He got his mother to find out the girl’s ring size, and he made plans for a romantic proposal.
However, she soon caught on to what he was planning. She promptly drove to his house and broke up with him. He never got a real explanation as to why she said no, but now he is happily engaged to another woman, so maybe things worked out for the better.
