The Top 8 Most Hilarious Dating Disasters Courtesy of the Darwin Awards

The Short Version: When a harebrained sexcapade leads to severe injury or premature death, the Darwin Awards is there to tell the story and honor those poor fools who get mixed up in ridiculously avoidable accidents. The Darwin Awards has posted over 800 stories about imprudent individuals who improve the human gene pool by failing to live long enough to reproduce. From heedless rulebreakers to foolhardy inventors, the website covers all sorts of lethal mistakes and absurd situations. We’ve picked out the top eight dating-related stories on the Darwin Awards to give our readers a small chuckle and a valuable lesson about what can happen when you let your libido do the thinking for you. Having sex while driving kills. Now you know.

My last boyfriend was too reckless for my liking. I used to joke that all his stories ended with, “And then we ran away.” One afternoon, we went to a lakeside party that spun out of control when his friends started drunkenly pointing and firing fireworks at one another because they thought it was funny to watch people dive out of the way. Then someone tripped and sent a lit firework tumbling into the grass. And then we ran away.

While we were dating, my ex often chose to do unsafe things, like make his best friend steer a car from the passenger seat, to prove he was daring. He bragged about it to me and shrugged off the risks. He said he’d never let anything stop him from doing what he wants to do. I told him that’d make a lovely inscription on his tombstone.

If he’s not careful, he could end up featured on the Darwin Awards one of these days. This website catalogs the ludicrous accidental deaths (and close calls) of everyday people who knowingly put themselves in dangerous situations — and paid the price.

Since 1993, the Darwin Awards has posted more than 800 stories about people making idiotic choices and winding up embarrassed, injured, or dead. Some valuable lessons and laughs can be gotten from these misbegotten adventures and cringeworthy accidents — like maybe don’t use cocaine as a sex stimulant.

The Darwin Awards highlights the horrible decision-making skills of grenade jugglers, train jumpers, and other deceased daredevils.

If you know of a foolhardy true story worth nominating for a Darwin Award, you can make a submission here. We spoke with Wendy Northcutt, creator of the site, to get her take on the site’s most popular dating-related cautionary tales. “I enjoy collecting these ludicrous stories of humans who intentionally set out with this brilliant, but obviously doomed, plan,” she said. “At least they’ve improved the gene pool, so there’s a little honor in that.”

From first dates to sexual fetishes, the Darwin Awards covers all kinds of idiotic and dangerous behavior. Who knew that driving two scooters at ramming speed into one another wasn’t the way to win a girl’s affection? Apparently not these two Taiwanese students who gave their lives in a game of chicken in 2004.

If you want to impress a date, you’re better off staying alive long enough to procreate. Some of these stories are shocking, and others are amusing, but they all serve as life lessons to anyone intent on pursuing their desires heedless of the consequences.

First off, we’ve got a 1999 story about people who died while having sex in a car with the engine on. According to “Couple Dies in Hearse,” carbon monoxide poisoning killed two Russian paramours in their own garage as well as a Mexican couple in a hearse parked in a warehouse. At least they went out with a bang.

Avoidable death is the hallmark of a Darwin Award, and this is a stupidly easy mistake to make in the heat of the moment, so it goes at the top of our list. On a related note: Having sex while driving is also a bad idea liable to put you on the fast track to a Darwin Award. Rest in peace, young lovers. Hopefully, others will learn from your mistakes.

“My mission has always been to treat the people who passed with respect,” Wendy told us. “I sympathize with them because I’m a major klutz, and I can just see myself hatching a brilliant scheme that winds up killing me.”

The next story comes from headlines in the UK in November 2000. Martin, a married man with an asphyxiation fetish, behaved with flagrant disregard for his own life in hopes of getting off while he was alone in his house.

Martin suffocated himself using a plastic bag and vacuum cleaner.

Reportedly, the 34-year-old man often asked his wife to hold her nightie over his face while they had sex. The sensation of being suffocated is arousing to some people, and, when practiced safely between consenting adults, this won’t usually get you on the Darwin Awards website.

It’s when a person escalates such desires to unhealthy levels that unfortunate accidents can sometimes occur.

One fateful afternoon, Martin apparently wanted to increase his solo pleasure by decreasing his ability to breathe. He put a plastic bag over his head and used a vacuum cleaner to remove the air inside.

It didn’t end well. According to the Darwin Awards article: “He was found lying by the still-running vacuum cleaner, fully clothed, dead, still holding the plug.”

If you’re a lonely single walking by yourself in the rain, you might think things couldn’t get worse. Well, 41-year-old Xian would probably tell you otherwise. He shows daters everywhere that boredom, horniness, and park benches are a very bad combination.

Xian’s private moment became a public spectacle when he got stuck masturbating to a bench.

“Bench Press” tells the story of a middle-aged man engaging in some lewd activity and embarrassing himself quite thoroughly. It all started with a trip to the park. The steel sit-up benches at LanTian Park have hundreds of little holes running along the surface. Xian saw that as an invitation to insert his penis in one of them. Hard to see how such an inspired idea could go wrong, right?

As soon as Xian became fully aroused, he became totally stuck. Try as he might, he was unable to remove himself from his prone position on the bench. Awkward.

The poor guy had no choice but to call the authorities and explain between panicked breaths the unfortunate situation he found himself in. It took four grueling hours to free Xian from the bench. In the end, emergency workers had to cut the entire bench free so they could take him to the hospital. Talk about being caught with your pants down!

This story takes unsafe sex to new heights. Experimental sex is pretty common among 21-year-olds, but one South Carolina couple topped them all with an ill-advised romp on the roof.

Just before dawn, the young man and woman were discovered lying bleeding and naked in the middle of the road. A cab driver called for an ambulance, and they were rushed to the hospital. But both passed away without regaining consciousness.

“Bottom line: If you put yourself in a precarious position at the edge of a pointy roof, you may well find yourself Falling in Love at the same time.” — an excerpt from “Falling in Love,” a Darwin Awards story from 2007

The cause of their deaths was a mystery until investigators found two sets of neatly folded clothes on a nearby rooftop. Authorities then concluded that the young lovers were having sex when they accidentally fell to their deaths. It turns out rolling around naked on a slanted roof is dangerous. Hindsight is 20/20.

Showing off is a common theme on the Darwin Awards. “Men especially have a tendency to show off to get attention,” Wendy commented. “I try to avoid stereotyping people. We all do dumb things, but it does favor men — I’m sorry, they’re just more likely to be risk-takers, apparently.”

That can certainly be said of this next dater who decided it was a good idea to step in front of a train to impress his date. The man yelled, “Train dodge!” and jumped across the tracks in front of an approaching train. But his timing wasn’t quite right.

“They found his remains spread along about 150 feet of the track,” the article reads. “I’m sure it was a date that the young lady will not soon forget.” Seriously.

This is a cautionary tale about kinky sex gone awry. An anonymous At-Risk Survivor got tied up in an awkward and dangerous position in 1999. One night a fire broke out at the Hyatt Regency Hotel in Cologne, Germany. A German billionaire businessman was in the middle of a raunchy affair with Ramona, a 28-year-old dominatrix he paid to bind, gag, whip, and humiliate him. However, he got more humiliation than he bargained for that night.

When Ramona heard shouting about a fire in the adjoining suite, she ran out without bothering to untie the unnamed executive. He was gagged, tied down, and unable to call for help. Firefighters were searching room by room when they found him caught in an extremely uncomfortable position. After they cut him loose, the red-faced tycoon had to flee the hotel wrapped in a sheet.

He escaped the fire but could not escape the mockery of witnesses. Still, this is one of the stories on the Darwin Awards that doesn’t end grimly. “Some people survive,” Wendy told us. “There are some near misses where it’s like ‘wow, that was almost fatally stupid.'”

It’s a universal dating truth that you don’t mess with New Yorkers. In “Call Girl,” the Darwin Awards shares the story of one 29-year-old rapist who had to learn that the hard way. He attacked a woman, stole $70 from her purse, and took her cell phone while threatening her in her own apartment.

Once he left, she called the police, who then urged her to aid in apprehending the man. So she called her attacker on her own cell phone and proceeded to work her feminine wiles on him.

“His victim really did a number on him!” — an excerpt from “Call Girl,” a Darwin Awards story from 2001

She invited him to come to her apartment for a date. Sure enough, the guy came knocking with a 40-ounce bottle of Heineken in his hand and her panties and cell phone in his pocket. What a way to return to the scene of the crime!

He was subsequently arrested by the police, and his bonehead story lives in infamy on the Darwin Awards.

Last of all is “Motorized Bar Stool,” which made it into Wendy’s book “The Darwin Awards Countdown to Extinction” because of its sheer hilarity. Cheers to this New Jersey resident who’s clearly not dating material. The 28-year-old made our list for his inventive and misguided means of traveling to a bar. On a motorized bar stool.

If his intention was to catch the eye of any ladies at the bar, he was unsuccessful. However, he did manage to crash while traveling at 20 mph down the road after consuming over 15 beers. “Although under the speed limit, he was over the drunk limit,” according to the story. This guy proves there’s really a fine line between drunken genius and bar-stool crash dummy.

“You can’t make this stuff up,” Wendy said with a laugh. “It’s really funny. Of course, he couldn’t win the Darwin Award because he survived.” One assumes it’s only a matter of time, though.

Sometimes people do dumb things in the name of love, or in the name of comedy, or just because. These stories give us a laugh, but they also provide a much-needed warning — especially to daters like my ex-boyfriend — about how “This seems like a good idea” can become “Wow, that was an obviously stupid and deadly mistake.”

You might think a death-defying act is just the thing to earn your partner’s esteem, but death is a definite dealbreaker in any relationship. Many of the people featured in Darwin Award stories don’t go on to live happily ever after. Because of serious errors in judgment, these unfortunate souls miss out on the chance to pass on their genes and enjoy a full life.

“Don’t let yourself win a Darwin Award,” Wendy warned. “Don’t do these things!”