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A couple on a date | Source: Getty Images
A couple on a date | Source: Getty Images

People Share True Stories of the Worst Dates They Have Ever Been On

Bettina Dizon
Feb 27, 2024
10:10 A.M.

First dates can be the thin line between a promising beginning and a swift end to potential romance. Five Reddit users shared what kind of worst first dates they had and how it either brought them embarrassment or danger.

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Going on a first date is a mix of excitement, nervous anticipation, and, sometimes, unexpected outcomes. Especially in online dating, with its vast sea of possibilities, it brings together people who might not have otherwise crossed paths.

However, it also opens the door to experiences that range from the awkward to the downright bizarre. Some Reddit users offered a peek into some of the worst first date stories they had, painting a vivid picture of dating mishaps.

A couple bonding over coffee. | Source: Getty Images

A couple bonding over coffee. | Source: Getty Images

One user shared a particularly memorable encounter with a man who seemed charming at first but soon revealed a quirk that was hard to overlook. As she revealed, she met her date on the online dating platform OKCupid and agreed to meet in person.

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However, during their date, he continuously interrupted her, leading her to confront him about his lack of interest in her responses. "I finally ask him '[Do] you want to hear anything I have to say?' He apologizes profusely, says '[You're] right, I'm so sorry!' and pulls out a pad of paper and a pen," the person wrote.

A man and an annoyed woman | Source: Shutterstock

A man and an annoyed woman | Source: Shutterstock

He began jotting down notes as she spoke. When she finally asked what he was writing, he revealed that he was listing things he wanted to tell her when it was his turn. While she did give him a second chance, things did not turn out well.

He even burned her a CD of his favorite music, despite her disinterest in music and disdain for math, demonstrated by the hundreds of pi decimals on the CD cover.

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A young woman holding a CD. | Source: Getty Images

A young woman holding a CD. | Source: Getty Images

A second Reddit user shared how her date was reminiscent of an action movie gone wrong. The woman shared how a seemingly simple outing turned perilous when her date's reckless driving led to a car accident.

"We were en route to our first destination and it was closed. So, he asked me where I wanted to go and I said, 'Hooters and bowling.' I know, keep it classy right here," the woman revealed. Her date was a reckless driver, an interesting turn of events after her parent warned her before leaving home, "just be careful and if he can't drive, get out the car."

A man driving with a woman beside him. | Source: Getty Images

A man driving with a woman beside him. | Source: Getty Images

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To make matters worse, the date's brakes stopped working until they crashed into the back of a truck. As if the crash wasn't shocking enough, her date fled the scene, revealing he had a warrant for his arrest. "I'm really sorry, I can't afford to go to jail again," the man yelled while running.

Left alone to deal with the aftermath and police, the date was memorable for all the wrong reasons, leaving her stranded and without even enjoying the planned Hooters and wings. She ended up giving the cops all of the man's details and even took a photo with the police car, posted it on Facebook, and tagged her date.

Two police officers smiling by their car. | Source: Shutterstock

Two police officers smiling by their car. | Source: Shutterstock

A third story illustrated how quickly a person's true colors can show. After bumping into a woman, and accidentally switching phones, the Reddit user agreed to meet the person at a coffee shop after work to swap back.

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"I walk up and see this very cute ginger wearing a suit dress. We chat for a bit: turns out she works at a bank, likes what I like, and is totally up for getting dinner this weekend," the person revealed.

A woman with red hair and freckles. | Source: Getty Images

A woman with red hair and freckles. | Source: Getty Images

However, come the weekend, a completely different person walked into the car for the date. The woman's drastic change in appearance from their first meeting to the date was the first sign of an unusual evening ahead.

Dressed in four-inch platform boots, a corset top, fishnet stockings, and spiked hair, the banker seemed to have a good sense of humor. What started as playful banter turned into a nightmare as she revealed deeply prejudiced views at a classy pub.

An empty restaurant. | Source: Getty Images

An empty restaurant. | Source: Getty Images

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When they got there, she made some mean comments about the waiter because of his race, which shocked the Reddit user. She even checked her food as if she thought the waiter might have done something to it because she was rude to him.

The person felt really bad and said sorry to the waiter for how his date acted. The waiter was nice about it, which made the person feel a bit better. After dinner, the date suggested more plans, still acting as if nothing was wrong. Instead, the Reddit user quickly took her home and couldn’t wait to leave after she said they should go out again.

Another Reddit user proved that awkwardness can happen with a date from an OkCupid match. According to the user, when he saw his date in person, she looked different from her profile. But what made the date even more unusual was that she didn't come alone. She brought a friend, who was only 16, her friend's toddler, and another friend.

An embarrassed man covers his face. | Source: Getty Images

An embarrassed man covers his face. | Source: Getty Images

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The diner setting quickly descended into chaos, with the toddler being given an energy drink and pouring the restaurant's bottled sugar all over their table. To make matters worse, the three girls did not try to include the Reddit user in their conversation. The date ended with a quiet exit and a generous tip left for the diner staff.

A fifth share on Reddit revealed that a clown school existed. While on their first date and diving into get-to-know-you conversation, the man asked about his date's job and if she enjoyed her line of work.

A woman dressed as a clown. | Source: Getty Images

A woman dressed as a clown. | Source: Getty Images

She revealed she was attending clown school, even demonstrating by pulling out a red clown nose and wearing it. This revelation came as a shock, especially since it was their very first date, a time both were presumably trying to make a good impression.

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Despite his surprise, he played along, asking if she was attending "clown university" or something similar, trying to keep the mood light and humorous. "And then she took my joke as an attack," he revealed as the reason the date ended.

First dates often don't go as a person plans them to be. In a similar story, a man went on a first date only to discover that the person they would meet up with was disabled.

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