You know things are off when even the waiter can sense the romantic doom before the appetizers arrive. First dates are already nerve-wracking, but these tales from the serving staff reveal just how spectacularly bad things can get. If you’ve had a cringeworthy date, these stories might make you feel a little better.

1. A Valentine’s Day Disaster

One Valentine’s Day, a man brought his date to a cozy dinner. They laughed, dined, and made an impression on their server. Fast forward two months, and the same man returned, this time with his wife. The server, unaware of the switch-up, casually mentioned how much he enjoyed serving them on Valentine’s Day. Cue the wife storming out and the man’s silent shame. Safe to say, that guy didn’t show up at the restaurant again.

2. Sushi Surprise Gone Wrong

A man excitedly picked up sushi to surprise his girlfriend, only to return 30 minutes later, asking for a refund. Why? She had a seafood allergy and was furious about the wasted money. While the restaurant couldn’t refund the sushi, they whipped up a chicken hibachi meal on the house. Sometimes, it’s the thought that counts… until it’s not.

3. When Food Came Before Love

In a small two-story restaurant, a couple was seated upstairs, enjoying their meal. The woman went downstairs to the restroom, tripped, and hit her head. As staff rushed to help and called an ambulance, the man calmly finished his meal – including her portion. When asked if he wanted to accompany her to the hospital, he declined. Talk about cold-hearted!

4. The Duck That Stole a Proposal

A man planned a romantic fountain-side proposal with a sign and friends to help set the scene. What he didn’t plan for was a mischievous duck stealing the engagement ring! After a frantic two-hour search, they found the ring in the fountain, and she still said yes. At least they’ll have a unique story to tell their grandkids.

5. Tinder Swipe Mid-Date

During a painfully awkward dinner, a man dominated the conversation, leaving his date visibly uninterested. When the server asked if it would be one bill or separate, the woman quickly said, “Separate!” As she paid, the man casually pulled out his phone and started swiping through Tinder. Guess he didn’t think the date was worth salvaging.

6. A Self-Obsessed Monologue

One server witnessed a man spend the entire date talking about how “special” he was and how his mind worked differently from everyone else’s. The woman barely managed to get a word in before being interrupted every time she tried. The cringe factor was high, and the date was undoubtedly doomed.

7. A Valentine’s Day Shift from Hell

A waitress working a packed Valentine’s Day shift had to serve her own boyfriend, who brought another woman to the restaurant. He was trying to make her jealous after she said she couldn’t celebrate that night because of work. His antics made the other woman uncomfortable and left the waitress mortified. Needless to say, their relationship ended there.

8. Anniversary Dinner Gone Wrong

A young couple celebrating their one-year anniversary walked into a seafood restaurant. The server, following protocol, asked about food allergies. The girlfriend’s response? A sad look at her boyfriend as she said, “I’m allergic to fish and shellfish.” Despite dating for a year, he hadn’t picked up on this crucial detail. Talk about an anniversary fail!

9. The Interrogation Date

One server described a date where the woman grilled the man about his salary, career plans, and financial stability over steak and salad. The man’s discomfort was palpable, and the server felt like they were serving at a job interview rather than a romantic dinner. Unsurprisingly, there was no spark to be found.

10. A Proposal That Fell Flat

An elderly man attempted a sweet proposal to his partner at a restaurant. Unfortunately, he tripped while trying to kneel, and paramedics had to be called. Amid the chaos, the woman left her dentures on the table. The manager ended up driving the dentures to the hospital. Love knows no bounds – or teeth, apparently.

Conclusion

Dating is a rollercoaster, and not every ride ends smoothly. These stories highlight how unpredictable and awkward first impressions can be. Whether it’s bad timing, mismatched priorities, or a meddling duck, these moments remind us that love is never as simple as the movies make it seem. At the very least, these mishaps provide plenty of laughs – and maybe even a lesson or two.