Everyone loves a good love story, but when you’re single or competitive, sometimes it’s nice to hear a story about an epic romantic fail to help cheer you up. That’s why we’ve decided to help brighten your Valentine’s Day with this depressingly hilarious list of romantic misfires. If you’re alone on the holiday, it should help remind you that relationships don’t always mean smooth sailing. If you’re in a relationship, these stories might just help you avoid tragic mishaps of your own. Whatever your specific situation this year, have a happy Valentine’s Day and try not to end up like one of these poor suckers.

Bottoms Up, Rings Down!

Putting a ring inside your girl friend’s Wendy’s Frosty may seem romantic, but when you and your friends encourage her to chug it, you might just ruin the surprise. At least, that’s what happened to Reed Harris, when his girlfriend, Kaitlin Whipple, opened up her gullet and downed the contents on her Frosty, only to see her cheering crowd suddenly go blank and look at each other with worry. “I felt nothing at all,” she told Lauer. “I was racing my friends, so there was no way I was going to lose that competition.” That’s right, Kaitlin drank her engagement ring and had to go to the hospital, where the ring was found via X-ray. Reed proposed to Kaitlin with the X-ray image of the ring in place of the actual jewelry. A few days later, with the help of plenty of fiber, the couple recovered the ring --and promptly had it cleaned! Source: MSNBC Image via Kaitlin's Website.

Try Chewing Next Time

Lest you think that Kaitlin is the only woman to have swallowed her diamond ring during an engagement proposal gone wrong, here’s a proposal story that “takes the cake.” Mr. Chen, a resident of China, thought it would be really romantic to bake his engagement ring into a cake to surprise his girlfriend. Chen said he was inspired by romantic comedies he’s seen, which always tends to be a bad start. His girlfriend, Wen, was eating the cake when he bent down on his knee to propose, and then she suddenly passed out. "I realized I had just swallowed the ring with a full mouth of cake," she said. Chen called the police who told him to visit the hospital, where they were able to use a catheter to remove the ring. When Wen woke up, she promptly said yes. Source: Ananova Image via Chotda [Flickr] (not the actual cake in the story)

Leaves Your Emotions Soaring

Admittedly, giving your girlfriend a balloon and then having a ring fall out when you pop it is really romantic, but I’m sure we can all see the infinite number of things that could go wrong through this method of “popping the question.” Lefkos Hajji didn’t consider all those potential problems when he had a florist hide a ring worth over $1,000 inside a balloon. Thought the florist warned him to hold on tight to the balloon, Lefkos lost the balloon moments after leaving the shop when a gust of wind tore it from his hands. He claims he chased the balloon in his car for two days before he gave up hope. "I just watched as it went further and further into the air. I felt like such a plonker. It cost a fortune and I knew my girlfriend would kill me.” While Lefkos may get a lot of points on the romantic scale, his inability to see the obvious dangers in this plan indicate that he may be a little short on the intelligence side. Evidence that his IQ is lower than the average bear is even stronger when you consider that the girl he is so in love with, presumably for her kindness and lovingness, refuses to speak with him until he gets her a new one. Personally, I would laugh and feel bad if my boyfriend did something like this. Of course, I think if he were to come up with a plan like this, he’d have an easy work around to prevent the danger from ever happening. --For example, this all could have been avoided if Lefkos put a note that said “will you marry me” in the balloon and then handed the girl the ring when she read the note. It’s just as sweet, not as dangerous. Source: The Sun UK Image via Kaptain Kobold [Flickr] (not the balloon in the story)

Rejection is Better In Private









I’ve always thought that if you were going to ask a girl to marry you in front of a massive audience, you’d better know she’s going to say yes. In this situation, even if the girl says yes, you still can’t be sure she actually meant it when she had that much pressure on her to agree. Of course, not every girl will say yes no matter how much she feels pressure, as seen in the video above, where a woman rejects her prospective husband in front of a full arena and tv cameras. Video link

The Rejection Should Not Be Televised













Like women swallowing wedding rings, rejecting potential spouses in public is not entirely uncommon. This woman’s face tells the answer before he even asks. This could have been a really romantic moment of television, but when the girl’s obviously not into it, the result is just plain awkward…not to mention painful. This couldn’t have been good for the show’s ratings. Video link

Keep Your Feet On The Ground

Sometimes all it takes for a proposal to go wrong is a little too much romance. When one man proposed on top of a steep hiking trail, the girl was so excited that she managed to fall off the cliffs after excitedly saying yes. She dropped ten feet off a steep rockface (like the one seen above) and went unconscious after hitting the ground. Luckily, park police were able to fly her out of the area with a helicopter and none of her injuries were life-threatening. Source: NY Daily News Image via Sharron McClellan [Flickr]

You Have The Right To Be An Idiot

It’s generally not a great idea to use government resources to scare the hell out of your girlfriend just so you can pop the question, but Baltimore State Delegate Jon S. Cardin is far too much of a risk-taker to heed such common sense. As such, he thought it would be a great idea to borrow a friend’s yacht and then convince local, on-duty police to raid the vessel with both boats and a helicopter, all in a strange, elaborate method of proposing to his girlfriend. Officers searched the boat and Megan Homer thought she was about to be handcuffed when Jon bent down on one knee and asked for her hand. Unfortunately for Mr. Cardin, officials for the Baltimore Police Department asked for his explanation. The officials were furious to hear about such an abuse of police resources when the city was already strapped for resources and police were in short supply even at dangerous crime scenes. Anthony Guglielmi, the Police Department's chief spokesman, stated "The Police Department is not in the business of renting out the helicopter and the boats for bachelor parties and birthdays. We're in the business of upholding public safety in Baltimore." When Cardin actually addressed the public about the matter, he claimed the police performed a “routine safety check,” and left out the part about the helicopter. At least he promised to reimburse the city for any expenses related to the proposal. Source: Baltimore Sun Image via Chris Hau [Flickr]

Don’t Kiss Someone To Deaf

Marriage proposals are not the only romantic gestures that go wrong of course. Even something as simple as a kiss can go very, very wrong in some situations. Take for example the Chinese woman who became partially deaf for two months after receiving a mind-numbingly passionate kiss from her lover. Somehow the kiss created pressure build up in her head so severe that her right ear drum blew out, leaving it completely deaf. "While kissing is normally very safe, doctors advise people to proceed with caution," said the Chinese newspaper that originally covered the story. Source: Reuters Image via Life Photographer Alfred Eisenstaedt

The Kiss Heard Round The World

Speaking of kisses that really make an impact, it’s important to know the cultural implications of public displays of affection before you kiss someone publicly on stage. Richard Gere learned this the hard way when he managed to piss off practically everyone in India by kissing the Celebrity Big Brother winner, Shilpa Shetty, on stage during an Aids awareness rally in New Dehli. In India, it is considered obscene to publicly display any form of affection and Gere’s kissing Shetty’s hands and face were considered vulgar to those watching. Some people were so incensed by his actions that they actually burned effigies of him on the street, while protesters in other areas shouted “death to Shilpa Shetty.” Source: BBC

Only Some Things Are Forever

Getting a life-sized portrait of your wife and children tattooed on your back might not be on most people’s to do list, but it most certainly displays a life-long commitment to your spouse. Unfortunately for Alan Jenkins, his wife was most certainly not willing to return the favor. While he was going through the 20-hour long, $1500 process of a full-back tattoo, she was busy cheating with a man who was 10-years-her-junior that she met at work. Of course, Alan didn’t find out until after the tattoo was complete, "I had it because I thought we loved each other - I feel very betrayed." Strangely, he’s decided to not have her image removed. His wife, Lisa, tried to defend herself by saying she never meant to fall in love with fitness instructor Kaspars Gavars and that she never wanted Alan to get the tattoo in the first place. Still, waiting for your husband to complete his tattoo before you tell him about your affair is pretty heinous. This incident reminds me of the scene in “Born In East L.A.” where Cheech is told to remove the tattoo of a woman on someone’s back. Since he obviously can’t remove it, he draws devil horns and a mustache on the face. Maybe Alan needs to see this movie for some ideas. Source: Daily Mail UK

Passengers Only Beyond This Point

In olden times, it was ok to walk your sweetie all the way down the tarmac just to spend the most possible time together before kissing each other goodbye, but in the days of the TSA, it’s not so simple. Personally, I thought this was pretty common knowledge, but I guess I was wrong because apparently, because one man actually shut down a whole airport for five hours just to kiss his girlfriend goodbye. The couple remains unidentified, but I’m sure more than a few people at the airport wish they knew who was responsible for making every single passenger go through security a second time, delaying flights for hours. The TSA agent that left his post, letting the man slip into the secure area undetected, was suspended on administrative leave. Source: Reuters Image

Only Babies Can Go Naked and Shoot People With Arrows

One of the most frequent reasons men seem to get in trouble for romantic gestures is in a strange attempt to impress a girl. While outrageous methods occasionally catch a woman’s eye, many stupid ideas not only fall flat, but also result in arrests and mayhem. James Miller is a perfect example. This young Romeo had a bit too much to drink one night and decided that relying on cupid wasn’t good enough to take his relationship to the next level --instead, he decided, he needed to be cupid. So he took the next logical step and jumped onto the field of a soccer game dressed in only his boxers, shooting roses from an arrow at the crowd of entertained onlookers. Naturally, he was arrested, fined and banned from any further soccer games for the next three years. Unfortunately for Miller though, his girlfriend, Jade Thompson, had quite the opposite reaction to his stunt and dumped him shortly after the incident. To make matters worse, since he’s in the military, his superior officers warned that he may even be court-martialed for the stunt. "That sort of behavior always seems to work some romantic magic in the movies. Now I have no girlfriend and no job,” he explained outside of a courtroom hearing. Source: Telegraph UK

Crime Doesn’t Pay or Get You Girls

What could be worse than streaking along a soccer field to impress a girl? Drunkenly stealing a plane and then crashing it into a soybean field. Michael Santos had already lost his driver’s license permanently, but that didn’t deter his desire to impress his girlfriend by showing her that he could fly a plane. So, he drove her to the airport while drunk, broke into a plane and then managed to catch the wing on fire before he even reached the end of the taxiway. He then missed a curve in the runway veered into a soybean field and cut up a bunch of the plants with the plane’s propeller. Police estimate the damage to be around $160,000. No word yet on whether his girlfriend actually stuck by him after this moronic stunt, but the fact that she got into the plane with her drunken boyfriend is a good indicator that she seems to lack common sense enough to dump him for this. Source: MSNBC Image via Cranky Guy Media [Flickr] (not the actual plane involved)

Don’t Flash Cash You Don’t Have

The spirit of capitalism is alive and well in China, or at least when it comes to trying to impress women. A man in the Heilongjiang province was arrested last year after trying to impress his girlfriend by depositing a 250 million yuan ($36.5 million) check into his bank account. The only problem, the check was a fake and he bought it only so he could look cool by depositing it in front of her. I’m sure you can guess what happened afterward; bank clerks knew the check was fake and called the police and the man was arrested. He immediately confessed that he bought the fake check for the sake of impressing his lover. The moral here is it’s better to be poor and honest than truthful while under arrest. Source: China Daily What about you readers? Have any love stories from hell, or know someone else that does? Do share.