Valentine’s Day is supposed to be about romance, grand gestures and memorable evenings. But not every first date ends with flowers and a second meeting.
In fact, some end with flashing police lights, court appearances, viral humiliation or even prison sentences.
To mark February 14, we’re looking back at ten first dates that went so wrong they made the news – from high-speed chases and kidnapping charges to bank robberies and extortion schemes.
If you think you’ve had a bad first date, these stories might put things in perspective.
#1 A Tinder Date That Ended With A Woman Stuck In A Window After Throwing Her Own Waste
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75points
#2 This Woman Tried To Get Her First Date Arrested Over A Crime He Never Committed
On June 16, 2023, 18-year-old Sumaya Thomas of North Liberty, Iowa, arranged to meet a man she had matched with on a dating app approximately one week earlier.
The man arrived at her home expecting a first date. Instead, police showed up.
According to an affidavit, Thomas called officers moments after the man arrived, claiming he was an ab*sive ex-boyfriend who had known her for two years. She told police he was threatening to “hit, punch, kick and stab her,” and falsely claimed she was pregnant with his child.
When officers detained the man, he insisted they had only recently met online. He provided messages between the two showing they had matched on a dating app days earlier.
“The conversation showed he was being honest and he really did just meet this female,” the affidavit stated.
Investigators later discovered she had deleted messages from her phone. She eventually admitted she fabricated the entire story because she “got cold feet on meeting him.”
The report added that she “didn’t think officers would help so she made up this call and the events that she described.”
The unnamed man was detained for more than an hour before officers determined the claims were false.
Thomas was arrested and charged with two counts of False Report of Indictable Offense to a Public Entity and one count of False Report on a 911 call, all misdemeanors.
The case resurfaced months later for a different reason.
By 2024, Thomas, then 19 and living in Dixon, Illinois, was arrested in Linn County, Iowa, on unrelated charges. Prosecutors alleged she stole more than $6,000 from two dependent adults while working as a caretaker for Limitless Potential, a nonprofit providing supported living services to individuals with intellectual disabilities.
According to the complaint, between March 3 and March 25, she used the victims’ debit cards without permission, stealing $5,834 from one and $878.27 from another.
A warrant was issued April 15, and she was later arrested and held in Linn County Jail on a $15,000 bond.
The man arrived at her home expecting a first date. Instead, police showed up.
According to an affidavit, Thomas called officers moments after the man arrived, claiming he was an ab*sive ex-boyfriend who had known her for two years. She told police he was threatening to “hit, punch, kick and stab her,” and falsely claimed she was pregnant with his child.
When officers detained the man, he insisted they had only recently met online. He provided messages between the two showing they had matched on a dating app days earlier.
“The conversation showed he was being honest and he really did just meet this female,” the affidavit stated.
Investigators later discovered she had deleted messages from her phone. She eventually admitted she fabricated the entire story because she “got cold feet on meeting him.”
The report added that she “didn’t think officers would help so she made up this call and the events that she described.”
The unnamed man was detained for more than an hour before officers determined the claims were false.
Thomas was arrested and charged with two counts of False Report of Indictable Offense to a Public Entity and one count of False Report on a 911 call, all misdemeanors.
The case resurfaced months later for a different reason.
By 2024, Thomas, then 19 and living in Dixon, Illinois, was arrested in Linn County, Iowa, on unrelated charges. Prosecutors alleged she stole more than $6,000 from two dependent adults while working as a caretaker for Limitless Potential, a nonprofit providing supported living services to individuals with intellectual disabilities.
According to the complaint, between March 3 and March 25, she used the victims’ debit cards without permission, stealing $5,834 from one and $878.27 from another.
A warrant was issued April 15, and she was later arrested and held in Linn County Jail on a $15,000 bond.
39points
#3 A First Date That Turned Into A High-Speed Police Horror
37points
#5 He Asked Her To Enter His Vehicle So He Could Give Her Flowers, Then Tried To Abduct Her
On June 2, 2010, a first date in Mountain View, California, ended with a kidnapping arrest after a woman said she was not allowed to leave her date’s vehicle.
According to Mountain View police, a 31-year-old woman from Sunnyvale told officers she had been persuaded to enter a van parked on the 200 block of Castro Street so her date could give her flowers.
Once she was seated in the passenger seat, the man began driving.
Police said the woman told them he refused to let her out of the vehicle. As the van slowed near White Oak Lane and Lawrence Expressway in Santa Clara, she opened the passenger door and fled.
She ran to a nearby 7-Eleven and called 911 at approximately 1:40 am.
Santa Clara police located the van and detained Charles Robinson, 24, of Redwood City, until Mountain View officers arrived. He was arrested and charged with kidnapping.
“No one has the right to deny another person the freedom to leave a social situation,” one person wrote. “This woman is a victim here.”
“A gentleman should present the flowers to the lady, not ask her to come and fetch them from his van,” another said. “That should have been a clue right there that this guy was up to something or, at the very least, not worthy of her time.”
According to Mountain View police, a 31-year-old woman from Sunnyvale told officers she had been persuaded to enter a van parked on the 200 block of Castro Street so her date could give her flowers.
Once she was seated in the passenger seat, the man began driving.
Police said the woman told them he refused to let her out of the vehicle. As the van slowed near White Oak Lane and Lawrence Expressway in Santa Clara, she opened the passenger door and fled.
She ran to a nearby 7-Eleven and called 911 at approximately 1:40 am.
Santa Clara police located the van and detained Charles Robinson, 24, of Redwood City, until Mountain View officers arrived. He was arrested and charged with kidnapping.
“No one has the right to deny another person the freedom to leave a social situation,” one person wrote. “This woman is a victim here.”
“A gentleman should present the flowers to the lady, not ask her to come and fetch them from his van,” another said. “That should have been a clue right there that this guy was up to something or, at the very least, not worthy of her time.”
28points
#6 She Threatened Her Date With Homicide If He Ever Left Her
25points
#7 This Date Ended With A Man Extorted, Kidnapped, Robbed, And Forced To Pose Bare
On December 10, 2022, a 30-year-old man in Pierce County, Washington, called 911 after a dating app meetup escalated into what authorities described as a robbery, kidnapping and extortion attempt.
According to the Pierce County Sheriff’s Department, the man arranged to meet a woman through Plenty of Fish and went to an apartment complex in Parkland.
Inside the apartment, investigators said another man appeared, ordered him to remove his clothes, and demanded his money, keys and cellphone. A woman took photos of the victim to use in an extortion scheme.
Deputies said the pair forced him to unlock his phone and attempted to transfer $6,000 to themselves, but the transaction was blocked as fraudulent. Before releasing him, they threatened to send the photos to his contacts if he reported what happened.
The following day, deputies returned to the same apartment on a domestic violence call and identified one of the individuals as 22-year-old Jahmichael Anthony Jeter III. Authorities said that during his arrest, Jeter attempted to reach for a firearm and later damaged a patrol vehicle while trying to escape.
Prosecutors charged Jeter with first-degree robbery, first-degree kidnapping, first-degree extortion, first-degree unlawful possession of a firearm and first-degree malicious mischief. He was booked into the Pierce County Jail on $125,000 bail.
Deputies also arrested 19-year-old Hydea Marie Tharpe, who was charged with first-degree robbery, first-degree kidnapping and first-degree extortion. Her bail was set at $50,000.
According to the Pierce County Sheriff’s Department, the man arranged to meet a woman through Plenty of Fish and went to an apartment complex in Parkland.
Inside the apartment, investigators said another man appeared, ordered him to remove his clothes, and demanded his money, keys and cellphone. A woman took photos of the victim to use in an extortion scheme.
Deputies said the pair forced him to unlock his phone and attempted to transfer $6,000 to themselves, but the transaction was blocked as fraudulent. Before releasing him, they threatened to send the photos to his contacts if he reported what happened.
The following day, deputies returned to the same apartment on a domestic violence call and identified one of the individuals as 22-year-old Jahmichael Anthony Jeter III. Authorities said that during his arrest, Jeter attempted to reach for a firearm and later damaged a patrol vehicle while trying to escape.
Prosecutors charged Jeter with first-degree robbery, first-degree kidnapping, first-degree extortion, first-degree unlawful possession of a firearm and first-degree malicious mischief. He was booked into the Pierce County Jail on $125,000 bail.
Deputies also arrested 19-year-old Hydea Marie Tharpe, who was charged with first-degree robbery, first-degree kidnapping and first-degree extortion. Her bail was set at $50,000.
23points
#8 A First Date In The Middle Of A Hurricane That Went Nowhere
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21points
#9 She Went On A First Date, And Ended Up Being Involved In A Bank Robbery
On December 5, 2016, a Massachusetts woman picked up a man she had met on a dating app for their first in-person date.
By the end of the afternoon, she was sitting in a car outside a bank while he ran out with a firearm and stolen cash.
According to the Bristol County District Attorney’s Office, the woman drove from Chepachet, Rhode Island, toward North Attleboro, Massachusetts, after picking up Christopher Castillo from his parents’ home. The two had never met in person before that day.
As they approached a Bristol County Savings Bank branch, Castillo asked her to pull over. He exited the vehicle and went inside while she waited in the Nissan Maxima.
Inside the bank, prosecutors said Castillo showed a teller a firearm and demanded $1,000, saying he was “really hurting.” The employee handed over the cash.
Minutes later, he ran back to the car wearing sunglasses and a hat, holding the cash and the firearm.
“F**king go,” he told her, according to her statement to police.
She began driving but pulled over once she saw North Attleboro police cruisers with flashing lights behind them. She exited the vehicle and walked away.
Castillo remained inside the car. Police removed him after he struggled with officers and spit at them. Authorities recovered a .44 caliber weapon, later identified as an antique belonging to Castillo’s stepfather, along with the $1,000 taken from the bank.
Castillo later pleaded guilty to armed robbery and three counts of battery on a police officer. He was sentenced to three years in state prison for the robbery and an additional two years in the Bristol County House of Corrections.
The woman was not charged.
By the end of the afternoon, she was sitting in a car outside a bank while he ran out with a firearm and stolen cash.
According to the Bristol County District Attorney’s Office, the woman drove from Chepachet, Rhode Island, toward North Attleboro, Massachusetts, after picking up Christopher Castillo from his parents’ home. The two had never met in person before that day.
As they approached a Bristol County Savings Bank branch, Castillo asked her to pull over. He exited the vehicle and went inside while she waited in the Nissan Maxima.
Inside the bank, prosecutors said Castillo showed a teller a firearm and demanded $1,000, saying he was “really hurting.” The employee handed over the cash.
Minutes later, he ran back to the car wearing sunglasses and a hat, holding the cash and the firearm.
“F**king go,” he told her, according to her statement to police.
She began driving but pulled over once she saw North Attleboro police cruisers with flashing lights behind them. She exited the vehicle and walked away.
Castillo remained inside the car. Police removed him after he struggled with officers and spit at them. Authorities recovered a .44 caliber weapon, later identified as an antique belonging to Castillo’s stepfather, along with the $1,000 taken from the bank.
Castillo later pleaded guilty to armed robbery and three counts of battery on a police officer. He was sentenced to three years in state prison for the robbery and an additional two years in the Bristol County House of Corrections.
The woman was not charged.
21points
#10 A Date With A Man So “Egomaniacal” She Considered Stop Dating Altogether
In 2023, 25-year-old Caitlin, a New York City resident, shared what she described as the “worst date” she had ever experienced in a TikTok video that quickly surpassed 400,000 views.
According to her account, she met a 43-year-old man at a bar in the West Village. Although she said she was not usually interested in older men, she agreed to a date after he appeared “cool, nice and well dressed.”
The following week, she met him at another West Village bar.
When she arrived, she said he was seated at a table with six of his male friends. Shortly after, two interns from his company joined them. She said she immediately felt uncomfortable.
Eventually, he asked for a separate table for the two of them.
During their conversation, she said he asked her age and reacted with relief when she told him she was 25. According to her retelling, he claimed that women in their early 20s “can’t keep up with him intellectually” and that he felt “too bad” for women in their 30s because they were “so desperate.”
She also said he repeatedly talked about himself and showed her photos of himself with celebrities.
At the end of the dinner, she declined his suggestion to continue the night elsewhere. She alleged that he told her he would not order her an Uber home unless she agreed to keep the date going.
Although she said she could easily arrange her own ride, she continued to another bar with him before ultimately leaving. While waiting for transportation, she said she overheard one of his friends ask him whether he had “got rid of that girl yet.”
Afterward, she posted a video describing the experience as the worst first date of her life and said it made her reconsider dating altogether.
According to her account, she met a 43-year-old man at a bar in the West Village. Although she said she was not usually interested in older men, she agreed to a date after he appeared “cool, nice and well dressed.”
The following week, she met him at another West Village bar.
When she arrived, she said he was seated at a table with six of his male friends. Shortly after, two interns from his company joined them. She said she immediately felt uncomfortable.
Eventually, he asked for a separate table for the two of them.
During their conversation, she said he asked her age and reacted with relief when she told him she was 25. According to her retelling, he claimed that women in their early 20s “can’t keep up with him intellectually” and that he felt “too bad” for women in their 30s because they were “so desperate.”
She also said he repeatedly talked about himself and showed her photos of himself with celebrities.
At the end of the dinner, she declined his suggestion to continue the night elsewhere. She alleged that he told her he would not order her an Uber home unless she agreed to keep the date going.
Although she said she could easily arrange her own ride, she continued to another bar with him before ultimately leaving. While waiting for transportation, she said she overheard one of his friends ask him whether he had “got rid of that girl yet.”
Afterward, she posted a video describing the experience as the worst first date of her life and said it made her reconsider dating altogether.
-23points