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Top 10 Worst Dating Experiences

by Shannon Quinn
fact checked by Jamie Frater

Dating can be fun. But for the most part, trying to find a new significant other is filled with awkward interactions with complete strangers. Even when you think you know somebody, dates can sometimes end up being a disaster.

Almost everyone has at least one dating horror story. But they probably can’t top the following 10 experiences.

10 Next Time, Use A Plunger

Photo credit: BBC

Liam Smith was having a great night in Bristol. He had met a girl on Tinder, and they went out for a nice dinner. They decided to continue the date back at his apartment with a bottle of wine and Netflix. The woman told Smith that she just needed a minute in the bathroom—and took a dump.

After she was done, she tried to flush but it wouldn’t go down. She was horrified. Things were going really well with this guy, and she didn’t want to ruin the mood with her floaters. So, in a state of panic, she grabbed her poo and tried to throw it out the window.

Unfortunately, the window didn’t actually open to the street. It was a double pane with a gap in-between. So, when she dropped the poo, it just rolled down and landed on the inside of the window, perfectly framed as a portrait of her indiscretion.

She attempted to fix the situation by reaching into the window to grab her poo. Once she was inside the window, her body got stuck in-between the panes. Smith had to call the fire department to dismantle the window and set her free.

When asked if he planned to go on another date with her, he optimistically replied, “We’ve already got the most difficult stuff out of the way first.”[1]

9 The Kiss Of Death

Photo credit: BBC

In prison, it’s difficult for a man to have a romantic date with his lady in the guest area while surrounded by guards. Inmate Anthony Powell was serving a life sentence for killing his mother-in-law. He met his new girlfriend, Melissa Ann Blair, through a friend named Brandy Pokovich.

Pokovich had used social media to hook him up with women who loved to date convicts. Melissa visited him at the Oregon State Penitentiary. At the end of their talk, Melissa and Anthony exchanged a passionate kiss.

Little did the guards know that Melissa was passing seven tiny balloons filled with meth into Anthony’s mouth. He swallowed them, planning to pass them in the bathroom later and retrieve them from the toilet.

Their plan backfired. The balloons ruptured in Powell’s stomach, and he died of an overdose. The judge ruled that Powell’s death was both of their faults and sentenced Melissa to two years of prison plus required treatments for her drug and mental health problems.[2]

8 Mismatched

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Darlene Daggett is an incredibly successful businesswoman working as an executive for the Pennsylvania-based home shopping network QVC. She had trouble finding the time to meet someone after having four kids and getting a divorce.

So she hired professional matchmaker Amber Kelleher-Andrews, who is based out of Los Angeles. Andrews charges $150,000 for her services to wealthy clients in exchange for access to her database of men and women who supposedly pass strict tests.

Daggett paid for the service and went on a series of truly awful dates. One man told her that he was still married. But his wife was terminally ill, so he just had to wait for her to die.

Another was a New York judge who had recently been on the news because he was caught up in a scandal for sleeping with an attorney. He passed out from heart problems on their first date.

Yet another married man went on a date with Daggett. When she turned him down because of his marital status, he began to stalk her. Later, he stole $10 million from someone else.

Finally, Daggett thought that she had met a great guy. He was an Australian entrepreneur, and she flew to California to meet him. He took her on vacation to Costa Rica and Panama. Things seemed to be going really well until he ghosted her.[3]

When she called him, he said, “I need to go dark,” claiming that he was a spy working for Interpol. She later learned that he had actually met up with his real girlfriend the next day. After dozens of ridiculously bad dates, Daggett sued Andrews to get her $150,000 back.

7 I Am Groot?

Brandon Vezmar was on a first date with a woman he had met on the dating app Bumble. They went to see the 3-D showing of Guardians of the Galaxy Vol. 2. According to Vezmar, the woman was texting on her phone “nonstop” during the movie.

He asked her to stop texting, but she didn’t listen. He told her that if she needed to use her phone, she should really do it out in the lobby because they would kick her out otherwise. So she left, stranding him at the theater alone without a ride home.

He responded like any perfectly sane 37-year-old man. He sued her for $17.31, which was the cost of the movie ticket, in small claims court. For Vezmar, texting during a movie is his biggest pet peeve. “It was like the date from hell,” he told the press.[4]

Later, his date told the press her side of the story. According to her, Vezmar was acting very strange when they first met and it made her feel uncomfortable. Her friend was having a crisis, so she needed to reply to the texts right away. She also kept her phone low so that she wouldn’t bother anyone. It only took her a couple of minutes to reply, and she was done.

She left because she already had bad vibes about him to begin with, and his snapping about the texting made her fear for her safety. She sees this lawsuit as proof of his mental instability. She is filing a restraining order against him because he also began to contact her family members to ask for the $17.31.

6 Absolutely No Chill

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Lindy Lou Layman looks like the stereotypical Texas beauty. At 29, this blonde bombshell works as a court reporter, and she met a successful attorney named Anthony Buzbee, who asked her out on a date. Unfortunately, her beauty was apparently skin-deep.

They were on their first date, and Buzbee took Layman back to his home. Layman got far too drunk, and for some unreported reason, she started to get very angry at him. She threw liquid on some of his paintings, including red wine all over his original Andy Warhol (which had cost him $500,000). She ripped his Renoir and Monet paintings off the wall and threw two sculptures across the room.[5]

He told her to get out and called her an Uber. Instead of leaving, Layman ran away and hid in a room in his mansion. He had to call the police. He estimates that she caused roughly $300,000 in damages to his art.

No one reports why she was so angry at him to begin with, but what everyone does mention is that Buzbee is good friends with Donald Trump. In 2016, Buzbee hosted a fundraising party for the president in his $14 million home, which is located on a golf course.

5 Material Girl

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Chris Thompson is a YouTube personality who lives in Los Angeles. He has a series called Tinder Terrors in which he explains his experiences using the dating app.

In 2015, he met up with a woman in her forties. Thompson was in his mid-to-late twenties, and they had an understanding that their meeting would be a casual encounter. They met up for dinner, and the woman showed up at the restaurant in a luxury vehicle. After their meal, they drove back to her mansion, where a maid answered the door.

They started drinking, and he became too drunk to drive home. They took the party upstairs. Things were going well. But when they were about to have sex, the woman pressed a button near the bed and the maid walked in with a condom.

His date proceeded to take Ecstasy and went into her closet. She emerged, dressed like Madonna, and started whipping his naked body with her long ponytail. He got very scared and called off the lovemaking session. Then he called for a ride home from Lyft.

The next day, he had to get another ride back to her house to pick up his car. On his windshield, there was a first-class plane ticket to New York City with a note that said, “See you soon.” He didn’t go.[6]

4 Wait For It

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Yevgeniy Vasilievich Bayraktar was born in Odessa, Ukraine. When he was nine, his mother met a much older man from Texas online. So they moved to the United States with him, and the two adults got married.

She asked her new husband to pay for her to go to nursing school. Almost immediately after graduation, she disappeared and called to ask for a divorce. She drove to one of the wealthiest places in the country—the Hamptons—and got a job there as a nurse.

Her master plan worked because she got married another two times to wealthy older men from New York. Yevgeniy Bayraktar grew up moving from place to place with his mother, watching her take advantage of men. As an adult, he spent less than a year in the air force before they discharged him.

At 26 years old, Bayraktar visited Japan and rented an apartment in Osaka. He met a woman named Saki Kondo on the dating app Tinder. She was never heard from again.[7]

One month later, Bayraktar was leaving his rental in Osaka with his luggage and the police stopped him. When he opened the bag, Kondo’s severed head came tumbling out.

3 Too Much Too Soon

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Contestants on The Bachelor and The Bachelorette are always such good-looking people that it’s a mystery why some of them need to go on a TV show to find love in the first place. One contestant, Peter Kraus, was the runner-up in 2018. During an interview, he was asked about his worst dating experience. He told a story of a first date that he’d had in Chicago.

When the woman showed up to dinner, she was already very drunk. Kraus tried to make things less awkward by starting a conversation. He learned that they both enjoyed football. Instead of being happy that they had something in common, the woman went straight to a horrifying confession.

She proudly explained that during college football games, she didn’t want to stand in line to use the porta-potties. So she would always pee her pants and let the liquid drip down her legs. Needless to say, they didn’t have a second date.[8]

2 A Twisted Tinder Trap

In December 2017, Mikayla Norris was 18 years old. She didn’t go to college, so she had a hard time making new friends or finding guys to date. She downloaded Tinder and picked up a young man named Kareem McCoy Lee so that they could go on a date.

When Norris never came home, her family and friends knew that something was wrong. The next day, her lifeless body was found lying on the ground. Lee had killed her, walked back to her car, and shot himself.

When the authorities looked into Lee’s social media accounts, they saw that he was making threatening posts on Facebook about wanting to attack his ex-girlfriend. They believe that he plotted to find a victim on Tinder whom he could carjack to drive himself to his ex’s house.

During their struggle, he killed Norris, possibly by accident. It appears that he regretted his actions so much that he chose to kill himself.[9]

1 You’ve Got Mail

In 2002, email was still a fairly new thing for a lot of people and many aspiring writers wanted to tell everyone about their lives. A woman named Jacqueline Kim wrote a long letter on her work email, analyzing Casey O’Brien, the man with whom she had gone on a date over the weekend.

She graded his outfit, car, haircut, and manners. She also revealed her true shallow nature, saying that his BMW, boat, and choice of a wine-tasting date upgraded him to an “A” instead of her first impression of a “B.” She admitted to getting very drunk on the date but still gave herself an “A+.” She wrote, “I was a BABE. He didn’t stand a chance.”

She was so confident that their first date went well that she wrote that she wouldn’t take the relationship to the next level unless he cut his hair and bought her gifts. She offered to set up her friends with Casey’s single, day-trading buddies.

Maybe Jacqueline should have thought twice before hitting “send” because the message didn’t just go to her friends. It circulated around the entire office and made its way onto the Internet and all the way back to Casey O’Brien himself.[10]

At that point, they had already gone on a second date. After reading the email, he realized that it was best to never call her again.

Shannon Quinn is an entrepreneur and writer from the Philadelphia area. You can find her on Twitter.


For more strange dating stories, check out 10 Dating App Murders and 10 Evil Exes That Will Put You Off Dating Forever.

fact checked by Jamie Frater