Some dates are filled with awkward moments that make you want to flee before they even start. Here, we explore some dating adventures that took a turn for the worse.
There’s something magical about meeting someone new—the thrill of anticipation, the shared laughter, the possibility of a lasting connection. However, as many who’ve ventured on several dates know, not every meeting transforms into a fairy-tale romance.
Despite hoping for a spark, some dates evolve into awkward episodes that prompt a swift exit, just like these amusing yet cringe-worthy encounters.
1. Thank God It’s Over
Imagine a first date where the cheerful conversation quickly turns into a one-sided complaint fest. A woman shared her experience where her date spent an entire hour complaining about everything in his life. Frustrated, she remained silent before they arrived at a restaurant.
While at the restaurant, her date insisted on ordering for her and ended up making a mess with a stubborn bottle cap, dripping juice everywhere. Adding insult to injury, he boasted about his home country’s superiority, ignoring her discomfort and the warnings from the restaurant staff.
When it came time to settle the bill, the woman suggested they split it, triggering a loud outburst from him. She left money on the table and walked out, but he still followed, spewing more criticisms.
Trying to end the night without a scene, she reluctantly allowed him to walk her home, where he shockingly made an unwanted advance. She firmly pushed him away, ending their interaction and warned him that further insistence would lead to police involvement.
The mortifying experience led to an encounter with his aunt the next day, who lived nearby. She shared the disastrous date story, leaving a lasting silence between their families.
2. Making the Exit
One Redditor shared a tale about a girl who chose an upscale restaurant for their date, racking up a $85 meal while staying mostly on her phone. Spotting his discomfort, the waitress discreetly suggested separate bills. He paid for his meal and quickly left, thankful for the waitress’s understanding.
3. A Kiss for Two
At 18 and stationed in the Air Force, a young man experienced an unforgettable date setup by his roommate. Arriving at the movie theater, his date brought along a massive blue rabbit stuffed animal for comfort during the film, which was a comedy.
After the movie and some ice cream, they returned to her cousin’s house. Standing at the doorstep, she humorously suggested he kiss both her and the blue rabbit, a suggestion he obliged while chuckling at the peculiar ending to their date.
4. Calling It Quits
In another tale, a man’s date surprised him at the movie theater, not with just her presence but with her family too: her parents and younger brother. As the movie rolled on, the brother continuously kicked his seat. Feeling overwhelmed, he discreetly excused himself and opted to leave, benefiting everyone involved.
5. A Baffling Request
A woman recounted her date at the London Zoo where, at the entrance, her date surprisingly asked if she could cover her own admission. Agreeing, she watched him activate a two-for-one voucher, allowing him to enter at her expense while he got in for free. This set the tone for an awkward day at the zoo.
Young couple on a date to a zoo | Source: Getty Images
6. A Major Turn Off
During a dinner, a woman experienced an unexpected reveal when her date’s wedding ring slipped from his wallet. Taken aback, she left money on the table and walked home in disgust, overwhelmed by the deceit and left without an appetite.
7. Where’s the Check?
Finally, on a first date, a man was confronted with a girl admitting she was engaged, but exploring other options to confirm her feelings. Startled by her honesty yet uncomfortable, he politely asked for the check and made his exit, avoiding further awkwardness.
Have you ever had a date slide into the realm of terrible? Sometimes it’s hard to tell who will leave you with a memorable experience—unfortunately, not always in a good way.
