First dates are always a gamble. You walk in with high hopes and butterflies in your stomach, but sometimes, the awkwardness becomes too much to bear—especially when the waiter starts sensing the date’s inevitable doom. Here are ten hilariously cringeworthy moments when servers witnessed the end of a romance before it even had a chance to begin.

The Valentine’s Day Disaster
Picture this: a couple dining out on Valentine’s Day, enjoying a romantic evening. They chat, they laugh, and everything seems perfect. Fast forward two months, and the same man brings a different woman—his wife—to the same restaurant.

The unsuspecting waiter, who remembers the earlier visit, innocently remarks, “It was great serving you on Valentine’s Day!” Cue the wife storming out and the husband sitting in silence, his head hung low. Needless to say, he never returned to the restaurant again.

Sushi Surprise Gone Wrong
One man thought he had the perfect plan: surprise his girlfriend with a feast of sushi. What he didn’t know? She had a severe seafood allergy.

When she discovered his costly mistake, she not only scolded him for spending so much but also made him return to the restaurant to plead for a refund. While the staff couldn’t take the sushi back, they felt bad enough to whip up a chicken hibachi meal for free. Lesson learned: always check your partner’s allergies before ordering!

A Love Left on the Stairs
In one of the most heartless displays of apathy, a woman dining with her partner fell down the stairs, hit her head, and passed out. The restaurant staff rushed to help and called an ambulance.

Meanwhile, her date casually walked to the stairs, peeked down, and returned to his table—to finish her meal. Even when the paramedics arrived, he showed no concern. He left 45 minutes later, having cleaned both plates and paid the bill.

The Fountain Proposal Fail
Proposals are supposed to be magical, right? This one didn’t quite go as planned. A man set up a romantic display near a fountain with friends helping out. Just as his girlfriend arrived, a curious duck swooped in and stole the engagement ring.

It took two frantic hours to recover the ring from the fountain. Thankfully, she still said yes, and the restaurant celebrated with free drinks all around.

Swiping Right During Dinner
One waitress couldn’t help but cringe when a man monopolized the conversation during a date. His partner barely got a word in edgewise, and her frustration was palpable. When the server asked if the bill would be together or separate, the woman quickly said, “Separate.”

As soon as the server handed the man his receipt, he pulled out his phone and started swiping through Tinder. Awkward doesn’t even begin to cover it.

The One-Sided Conversation
Some people just love to talk about themselves. One man spent an entire date rambling about how unique and special his mind was, cutting off his date every time she tried to contribute.

The woman sat there nodding politely, clearly counting the minutes until she could leave. Even the waiter felt secondhand embarrassment watching her endure the one-man show.

The Vengeful Valentine
Working in a restaurant on Valentine’s Day is already stressful, but one waitress had an unforgettable experience with a man she’d recently started dating. She had explained that working in food service meant no Valentine’s Day off, but he wasn’t having it.

Instead of waiting to celebrate later, he asked another woman out and brought her to the restaurant where his girlfriend was working—then sat in her section. He spent the entire night trying to make her jealous, but the only thing he accomplished was ruining both dates.

A Deadly Anniversary Choice
One couple came to celebrate their one-year anniversary at a seafood restaurant. Everything seemed normal until the server asked about allergies, and the woman gave her boyfriend a withering look before saying, “I’m allergic to fish and shellfish.”

The server ensured her meal was safe, but the disappointment on her face spoke volumes. Celebrating a milestone at a place that could literally endanger her life? Not exactly romantic.

The Steakhouse Interrogation
A first date quickly turned into a grilling session when a woman started interrogating her companion about his finances. She demanded to know how much money he made, where he worked, and whether he had plans for advancement.

The man, visibly uncomfortable, tried to avoid answering. Meanwhile, the waiter awkwardly served their food, feeling like an unwilling participant in a financial audit.

The Soup and Teeth Situation
Not all awkward moments involve young couples. At one restaurant, an elderly man proposed to his partner, only to trip and fall while kneeling. Unable to get up, the staff had to call an ambulance.

In the chaos, the woman removed her dentures to eat her soup, leaving them on the table. When the ambulance left, the manager ended up driving her teeth to the hospital.

Dating can be unpredictable, but these stories prove that some moments are better left in the past. From clueless partners to disastrous proposals, these encounters highlight the importance of communication, thoughtfulness, and self-awareness.

So, if your last date didn’t go as planned, take comfort in knowing it probably wasn’t as bad as these. Sometimes, the best thing you can do is laugh, learn, and move on. After all, love is a journey full of twists, turns, and unforgettable stories—just maybe not the kind you want to share with a waiter!