When it comes to the top 10 worst dating experiences, love can quickly turn into a series of bizarre, cringe‑worthy moments that leave you questioning humanity.
Why These Are the Top 10 Worst Dating Disasters
From clogged toilets to fatal kisses, each tale below showcases how a simple meetup can spiral into a nightmarish saga. Buckle up, because these stories are as outrageous as they are unforgettable.
10 Next Time, Use A Plunger
Liam Smith thought his Bristol evening was shaping up perfectly. He had matched with a girl on Tinder, enjoyed a nice dinner together, and then decided to keep the momentum going back at his flat with a bottle of wine and a Netflix binge.
Mid‑movie, his date announced she needed a quick minute in the bathroom and promptly proceeded to take a dump. When she tried to flush, the toilet refused to cooperate, leaving her mortified and desperate not to ruin the mood with a floating mess.
In a panic, she seized the offending waste and attempted to hurl it out the window. Unfortunately, the window was a sealed double‑pane unit, so the poo simply rolled down the inner pane and framed itself like an unwanted portrait.
Desperate to retrieve the evidence, she reached into the gap between the panes, only to become stuck. The fire department was summoned, dismantled the window, and finally freed her. When asked if he’d consider a second date, Smith dead‑panned, “We’ve already cleared the toughest hurdle first.”
9 The Kiss Of Death
Romance inside a prison’s guest area is a complicated affair, especially when guards loom nearby. Anthony Powell, a life‑sentence inmate for killing his mother‑in‑law, met his new girlfriend Melissa Ann Blair through a mutual contact named Brandy Pokovich.
Melissa, who specialized in dating convicts via social media, visited Powell at Oregon State Penitentiary. Their goodbye seal was a passionate kiss that seemed straight out of a thriller.
Unbeknownst to the guards, Melissa slipped seven tiny meth‑filled balloons into Anthony’s mouth, planning for him to later retrieve them from the bathroom toilet. The balloons, however, ruptured inside his stomach, delivering a lethal dose.
Powell died from an overdose, and the court held both parties responsible, sentencing Melissa to two years behind bars plus mandatory drug and mental‑health treatment.
8 Mismatched
Darlene Daggett, a high‑ranking executive at QVC, struggled to find time for romance after four children and a divorce. She turned to Los Angeles‑based matchmaker Amber Kelleher‑Andrews, who charges $150,000 for access to a curated database of vetted singles.
Daggett paid the hefty fee and embarked on a string of disastrous dates. One suitor confessed he was still married, yet his terminally ill wife forced him to wait for her death before moving on.
Another encounter involved a New York judge fresh from a scandal for sleeping with an attorney; he collapsed from heart complications during their first meeting. A third date was with a married man who, after being rejected, began stalking her and later stole $10 million from an unrelated party.
The final blow came when an Australian entrepreneur whisked her away to Costa Rica and Panama, only to ghost her with the excuse, “I need to go dark,” claiming he was an Interpol spy. Daggett eventually sued Andrews for a full refund of her $150,000 investment.
7 I Am Groot?
Brandon Vezmar’s first date with a Bumble match took place during a 3‑D showing of Guardians of the Galaxy Vol. 2. Unfortunately, his date spent the entire film glued to her phone, texting nonstop.
When Vezmar politely asked her to stop, she ignored him. He warned that if she needed to use her phone, she should step out into the lobby or risk being escorted out, prompting her to abandon the date entirely and leave him stranded.
Vezmar responded by filing a small‑claims suit for $17.31 – the exact cost of his ticket – claiming the texting was his biggest pet peeve. He told reporters, “It was like the date from hell.”
The woman later countered, saying Vezmar’s odd behavior made her uncomfortable, that she had to reply to a friend’s crisis, and that she kept her phone low to avoid bothering anyone. She also claimed he began contacting her family for the money, prompting her to seek a restraining order.
6 Absolutely No Chill
Lindy Lou Layman, a classic Texas beauty and court reporter, landed a date with successful attorney Anthony Buzbee. Their first evening took a wild turn when Layman became heavily intoxicated at Buzbee’s mansion.
In a fit of unexplained rage, she drenched Buzbee’s priceless artworks – sloshing red wine over an original Andy Warhol, ripping a Renoir and a Monet from the walls, and flinging two sculptures across the room.
Buzbee ordered an Uber to get her out, but instead of leaving, Layman hid in a hidden room, forcing Buzbee to call the police. He later estimated the damage at roughly $300,000. The motive behind her fury remains a mystery, though Buzbee’s close ties to Donald Trump and a 2016 fundraiser at his $14 million home have been noted.
5 Material Girl
Chris Thompson, a YouTube creator behind the series Tinder Terrors, recounted a bizarre encounter with a woman in her forties. After a dinner at a fancy restaurant, the woman arrived at her mansion in a luxury vehicle, where a maid greeted them at the door.
The night progressed with heavy drinking, and soon they were upstairs. Just as intimacy seemed imminent, the woman pressed a button, prompting the maid to appear with a condom in hand.
She then popped Ecstasy, retreated to a closet, emerged dressed like Madonna, and proceeded to whip Chris’s naked body with her long ponytail. Terrified, he called off the encounter and summoned a Lyft to get home.
The next morning, Chris discovered a first‑class ticket to New York tucked to his windshield with a note saying, “See you soon.” He never boarded.
4 Wait For It
Yevgeniy Vasilievich Bayraktar was born in Odessa, Ukraine. At nine, his mother married a much older Texan she’d met online, prompting the family’s move to the United States.
She persuaded her new husband to fund her nursing education, only to divorce him shortly after she graduated, relocating to the Hamptons and securing a nursing job. She then married two more affluent, older New York men, leaving Yevgeniy to shuffle between homes and witness his mother’s pattern of exploiting wealthy spouses.
As an adult, he spent less than a year in the Air Force before being discharged. At 26, he traveled to Osaka, Japan, and met a woman named Saki Kondo on Tinder.
One month later, while leaving his rented apartment, police stopped him. When they opened his suitcase, Kondo’s severed head rolled out, confirming the worst‑case scenario.
3 Too Much Too Soon
Peter Kraus, the runner‑up from the 2018 season of The Bachelor, recounted his most mortifying first‑date story during an interview. He had met a woman in Chicago who arrived visibly intoxicated.
Attempting to salvage the evening, Kraus discovered they both loved football, hoping common ground would ease the tension. Instead, the woman proudly confessed that during college football games she would deliberately pee her pants to avoid the long lines at portable toilets, letting the stream run down her legs.
The revelation was enough to end any chance of a second date, leaving Kraus to wonder how many other candidates might have hidden such odd habits.
2 A Twisted Tinder Trap
In December 2017, 18‑year‑old Mikayla Norris struggled to find friends and romance after skipping college. She turned to Tinder and matched with Kareem McCoy Lee, arranging a date.
When Norris never returned home, her loved ones grew alarmed. The following day, her lifeless body was discovered on a road. Investigators learned that Lee had killed her, then returned to his car and shot himself.
Social‑media sleuths uncovered Lee’s threatening Facebook posts about harming his ex‑girlfriend, suggesting he intended to use a Tinder victim as a means to reach his former partner’s house.
The tragic encounter appears to have been a botched attempt, with Lee regretting his actions enough to end his own life shortly after.
1 You’ve Got Mail
Back in 2002, when email was still a novelty, Jacqueline Kim composed a lengthy office memo dissecting her weekend date with Casey O’Brien. She graded his attire, vehicle, haircut, and manners, elevating his score from a “B” to an “A” after noting his BMW, boat, and wine‑tasting excursion.
Kim also boasted about her own drunken antics, awarding herself an “A+” and declaring herself a “BABE” who had the upper hand.
Confident in her assessment, she demanded that Casey cut his hair and buy her gifts before any further commitment, even offering to set up friends with his single, day‑trading associates.
The memo, however, didn’t stay confined to her inbox. It spread throughout the office, went viral online, and eventually reached Casey himself. By then, they’d already gone on a second date, but after reading the email, he decided never to call her again.