Some dates are so awkward and cringeworthy that the desire to end them arises even before they begin. These accounts highlight dating disasters that took a sharp turn for the worse, becoming unforgettable tales of mishaps and cringe-worthy moments.
In life, few things compare to the excitement of a promising date—the laughter, the potential for romance, and the hope for something meaningful. Yet, as many know, not all dates lead to love. Instead, they sometimes result in awkward stories, like the following dating misadventures.
1. The Date That Wouldn’t End
A woman shared her dating disaster on Reddit. She and her date chose to go for a walk, but he spent an entire hour complaining about every aspect of his life, not allowing her to get a word in. The disaster continued when they sat down for dinner. He ordered for her and ignored the bartender’s warning about a difficult-to-open drink, spilling juice on himself in the process. His arrogance shone through as he criticized the restaurant staff and boasted about his home country, all while she sat in discomfort.
When the bill arrived, she offered to split it due to his earlier complaints about money. Instead, he yelled at her, prompting her to leave cash on the table and walk out. But the ordeal didn’t end there—he insisted on walking her home, which led to an awkward, silent stroll. At her door, he tried to force himself on her, claiming she “owed him.” She pushed him away, threw extra money at him, and threatened to call the police. The following day, she shared the story with his aunt, ending their brief interaction forever.
2. A Pricey Exit
Another Reddit user recalled his disastrous first date at an expensive restaurant. His date ordered a $25 appetizer, a $45 steak, and a $15 drink while remaining glued to her phone, taking calls and texting throughout the meal. Observing his frustration, the waitress discreetly offered to split the bill. He gladly accepted, paid his portion, and left.
3. A Date for Two—And a Rabbit
An 18-year-old Air Force man went on a double date with his roommate’s girlfriend and her cousin. To his surprise, the cousin brought along a giant stuffed rabbit to the movies, claiming it provided comfort, even though they were watching a comedy. Later, when they arrived at her house, she insisted he kiss both her and the rabbit to avoid making it jealous. Despite the absurdity of the situation, he complied, noting that his date, while beautiful, was undeniably quirky.
4. A Family Affair
One man’s blind date took an unexpected turn when his date showed up at the theater with her parents and younger brother in tow. They all sat down to watch Gnomeo and Juliet, and to make matters worse, the little brother spent the first 20 minutes kicking the back of his seat. Eventually, the man excused himself to go to the restroom and never returned.
5. A Baffling Start
A woman shared a Twitter post about her first date at the London Zoo. Her date asked if she would mind paying for her own ticket, to which she reluctantly agreed. He then pulled out a two-for-one voucher, meaning she paid full price while he entered for free.
6. The Rookie Mistake
During a dinner date, a man’s wedding ring slipped out of his pocket while reaching for his wallet. The woman, disgusted, immediately threw some money on the table and left. It was one of the few moments in her life where she was too repulsed to finish her meal.
7. A Confession Over Dinner
On a first date, a man was taken aback when his date revealed, “I’m actually engaged, but I’m not 100% sure he’s the right one, so I’m going on a few dates to see if I change my mind.” Shocked, the man requested the check and made a swift exit.
These tales of dating disasters remind us that not every romantic endeavor will have a happy ending, but at least they leave us with stories to laugh about later.
