First dates are like uncharted waters—exciting, nerve-wracking, and often unpredictable. Sometimes, even with the best intentions, things can go hilariously or painfully wrong. These are 17 unforgettable tales of dates that took an awkward turn, leaving everyone involved with memories they’ll never forget (or wish they could).
The “Fine Dining Disaster”
One man found himself sweating bullets when his date, without hesitation, asked the waiter, “What’s the most expensive dish on your menu?” His heart sank, knowing he wasn’t ready to foot that kind of bill. The waiter, thankfully catching the panic in his eyes, responded, “I’m sorry, but that’s unavailable tonight.” The awkward tension was palpable, and while he tipped the waiter generously, the date ended with an expensive story he’d never forget.
The Shellfish Allergy Nightmare
A foodie guy insisted on picking the restaurant and ordering for both parties on a first date. Unfortunately, his overconfidence turned into a near-disaster when he ordered shellfish—completely ignoring his date’s allergy. Her throat began tightening after just one bite, forcing her to leave for treatment while he casually stayed behind to finish his meal. Safe to say, there wasn’t a second date.
Sweatpants, Not Blue Jeans
A woman on a blind date was promised that her mystery man would be in blue jeans and a t-shirt. After waiting 40 minutes, a man in sweatpants approached her and asked, “Are you waiting for me?” His excuse for the wardrobe malfunction? “My mom hasn’t washed my jeans yet.” That explanation, while amusing in hindsight, was enough to ruin any romantic vibe.
When Nerves Get the Best of You
Nerves can get the best of us, but for one couple, they took center stage. On their first date, the woman threw up just before her date arrived. To her surprise, when they reached their destination, he jumped out of the car and promptly vomited in the parking lot. “Food poisoning?” they joked, but both knew it was just anxiety taking its toll. Surprisingly, this awkward start blossomed into a long-lasting relationship.
The Ice Skating Debacle
For a first date, one man thought ice skating would be romantic—despite not knowing how to skate. Little did he know his date was a competitive figure skater who could literally glide circles around him. After watching him stumble repeatedly, she asked if she could do a few laps alone, leaving him floundering in embarrassment.
Mom’s Unexpected Cameo
A young teen’s first date was sabotaged by his well-meaning but overbearing mother. After dropping him off, she decided to stick around and “supervise” from a distance. When she noticed the couple heading in the wrong direction, she yelled, “You’re going the wrong way!” Embarrassed beyond belief, the boy could hardly make eye contact with his date for the rest of the outing.
The Valentine’s Day Fail
On a chilly Valentine’s Day, a man decided to surprise his date with flowers, chocolates, and a musical card. Unfortunately, freezing temperatures killed the flowers, the card made a horrific buzzing noise instead of playing a song, and the chocolates were the only thing that survived. Thankfully, his date found the whole ordeal charming and kissed him anyway.
The Dad Pop Quiz
After a late-night theater show, a man stayed at his date’s house to crash for a few hours. He woke up to her dad shaking him awake and demanding to know who he was. Things went from awkward to humiliating when the dad quizzed him on thermodynamics—his weakest subject.
Scooby-Doo Obsession
One woman’s date arrived wearing head-to-toe Scooby-Doo apparel, including a hat. While she tried to steer the conversation toward normal topics, he persisted in discussing nothing but Scooby-Doo episodes and characters. The date ended quickly, with her knowing there wouldn’t be a follow-up.
The Big Sleep, Literally
When two introverts were set up on a date, their shared love for classic movies seemed like a promising start. Unfortunately, the chosen movie was “The Big Sleep,” and the irony wasn’t lost when the guy fell asleep halfway through.
The Pizza Controversy
After ordering pizza for a Tinder date who was running late, one woman found herself the target of an unexpected outburst. The man was furious that she had paid for the meal, claiming he wouldn’t have eaten it if he knew “a woman paid for it.” Unsurprisingly, that date was over before dessert.
The Nosebleed Fiasco
Things were going well for one couple until a nosebleed ruined the mood. While making out, the man’s nose began dripping blood onto his date’s face. Panicked, he smeared it while trying to clean up, making matters worse. Mortified, she left, and there was no second date.
Grandma’s Game Show Night
A romantic movie night turned into an awkward family affair when a woman’s grandmother decided to join. The three of them spent the evening watching game shows instead of the planned romantic films, much to the dismay of her date.
Public Humiliation at the Bar
Feeling cocky after a few drinks, a man decided to playfully pretend to spill water on his date. Unfortunately, his hand slipped, and he actually dumped the entire jug on her head—right in front of the packed bar. The crowd’s laughter sealed the date’s fate.
The Ice Cream Revelation
A romantic ice cream outing turned sour for one man when he discovered his lactose intolerance—mid-date. As they walked down the street, the urge hit him, and he had no choice but to duck behind a bush. To make matters worse, a group of people on a nearby balcony noticed and yelled, “Look, that guy’s taking a poop!”
Puking on the First Date
An anxious woman tried to keep her nerves at bay during a dinner date. However, as soon as they left the restaurant, her stomach gave out, and she vomited all over the parking lot—and on her date’s sweater. Despite the mess, he graciously brushed it off.
The Missed Cue
After a great evening, a woman invited her date up for coffee, hinting at more than just caffeine. Oblivious, he replied, “No thanks, I don’t like coffee,” and left. Halfway home, it hit him what she actually meant, but by then, the opportunity was gone.
Conclusion: Embrace the Awkward
If there’s one thing these stories prove, it’s that awkward dates make for unforgettable memories—and sometimes even lasting relationships. Whether it’s a failed romantic gesture or a public mishap, these cringe-worthy moments remind us that love isn’t always picture-perfect. So, if you’ve had an awkward date, take solace in the fact that you’re not alone—and maybe laugh about it later!
