People Share Their Dating Experiences That Went Horribly Wrong

Certain dates are so cringe-worthy that the desire to end them arises before they even commence. The following stories delve into dating escapades that veered sharply into the worst imaginable scenarios.

In life, few experiences rival the thrill of a promising date—the anticipation, the laughter, the possibility of a connection that transcends the ordinary. But, as anyone who’s been on many dates knows, not all of them turn into fairy-tale romances.

Despite hoping for magic and sparks, some dates turn into awkward and cringe-worthy stories that make us wish for a quick exit, much like the following funny and unexpected dating mishaps.

Thank God It’s Over
One woman shared her horrible dating experience on Reddit. On their first date, they opted for a stroll, but her date dominated the conversation for a solid hour, airing complaints about every facet of his life without allowing any input.
Reaching a breaking point, he decided to call it quits, excusing himself to the restroom and opting to drive home instead.
Seated at a restaurant, he presumptuously ordered her food and, dismissive of the bartender’s warning about difficult-to-open caps, ended up spilling juice on himself. His arrogance surfaced as he criticized the staff, asserting the superiority of his home country. He continued his tirade about the perceived incompetence despite her discomfort in a restaurant she frequently visited.

As the evening unfolded, the man vocalized his intentions to become a manager and fire people he deemed incompetent. When the check arrived, the woman proposed splitting it, considering his earlier discussions about money issues. In response, he yelled at her. She left money on the table and walked away, but he persisted in ranting about his country’s supposed superiority.

In an attempt to avoid a scene, she agreed to let him walk her home when he kept insisting. The walk was marred by awkward silence, and upon reaching her front door, he attempted to force himself on her with the excuse that she owed him. She resisted, pushing him away and throwing additional money at him, declaring their interaction over. Safely inside, she sent him a stern text threatening police involvement if he didn’t leave.

The next day, faced with the audacity of his aunt, who lived nearby, she recounted the disastrous date and asserted that his family should have “raised him better.” Following this incident, the family never spoke to her again, which she didn’t mind.

In response to inquiries about his country, she clarified that he was from Serbia, emphasizing that his behavior stemmed from personal shortcomings and insecurities rather than being reflective of his nationality.

Making the Exit
A Reddit user recalled his first date with a girl who insisted on dining at an exceptionally pricey restaurant, where she ordered a $25 appetizer, a $45 steak, and a $15 drink. Throughout the meal, she remained glued to her phone, incessantly taking calls and responding to texts.
Observing this, the waitress discreetly signaled him. He excused himself, and the waitress offered to prepare separate bills. He gladly accepted. “That would be wonderful!” he replied, settling his portion of the bill before going home.

A Kiss for Two
At the age of 18, stationed in the Air Force and residing in the dorms, a man found himself set up on a date by his roommate with his girlfriend’s cousin. The group of four decided on a movie outing, where his date surprised everyone by bringing a colossal blue rabbit, not the typical small accessory one might find on a keychain.
She explained that the oversized stuffed animal offered comfort during movies, even though the chosen film was a comedy. Post-movie, the group opted for ice cream, and they subsequently drove to the cousin’s home.

As they reached the door, his date suggested he not only kiss her but also the gigantic stuffed rabbit named Pebbles to avoid potential jealousy. Reflecting on the peculiar situation, he emphasized that despite the eccentricity, he did indeed kiss Pebbles, considering his date to be exceptionally attractive but undeniably quirky.

Calling It Quits
A man’s friend once set him up on a blind date with a girl. They met at the theater, where the man realized her appearance differed significantly from her Myspace photos. To complicate matters further, upon entering the theater, she introduced him to her parents and nine-year-old brother, who joined them for the movie–”Gnomeo and Juliet.”

Perplexed but determined, he found himself enduring the cinematic experience, albeit with the added challenge of his date’s brother incessantly kicking the back of his seat for the entire 20 minutes. Reaching a breaking point, he decided to call it quits, excusing himself to the restroom and opting to drive home instead.

A Baffling Request
A woman recalled an experience on Twitter about their first date to the London Zoo. At the entrance, her date surprisingly asked if she would mind covering her own ticket, to which she agreed. The date then produced a two-for-one voucher, resulting in the woman paying for her ticket while he entered for free.

A Major Turn Off
A woman was in the midst of a dinner date with a man when his wedding ring accidentally slipped out of his pocket while he was reaching for his wallet–a “Rookie mistake” of storing both in the same place.

Overwhelmed by disgust at the situation, the woman promptly threw some cash on the table and decided to walk home. It marked one of the rare occasions in her life where she found herself too repulsed by circumstances to have an appetite.

Where’s the Check?
On a first date with a girl, a man was taken aback when she disclosed, “Actually I’m engaged but I’m not 100% sure if he’s the right one. So, I’m going to go out on a few dates to see if I change my mind.” It wasn’t long before the man requested the check and made a quick exit.

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