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Romance in the movies is supposed to make us swoon. But sometimes, it makes us cringe, laugh, or want to crawl under the table from secondhand embarrassment. While Hollywood has given us some of the most enchanting dates ever, it has also delivered some of the worst.
Here’s a look at the most disastrous romantic dates in cinema history, where love went terribly, awkwardly wrong.
1. The “Snails” Scene – Pretty Woman (1990)
Edward (Richard Gere) and Vivian (Julia Roberts) may have an iconic love story, but their fancy dinner date doesn’t exactly go smoothly. When Vivian, trying to keep up with the high-society setting, struggles with escargot, she ends up launching a snail across the room. The maître d’ saves the day with a smooth “It happens all the time,” but the moment is the definition of a high-class disaster. A prime example of how nerves can turn an elegant night into an embarrassing memory.
2. The Pie Scene – Dumb and Dumber (1994)
Harry (Jeff Daniels) finally lands a date with Mary (Lauren Holly) and completely ruins it in spectacular fashion. From his horrible small talk to his excruciating chili pepper accident, Harry’s lack of charm is painful to watch. But nothing tops the laxative prank pulled by Lloyd (Jim Carrey), leaving Harry in a truly humiliating situation mid-date. It’s a comedic train wreck that makes viewers appreciate their own awkward dating moments.
3. The Spaghetti Date – Lady and the Tramp (1955)
Yes, this is one of the most beloved romantic moments in cinema history, but let’s be real—it’s also pretty unhygienic. A back-alley dinner of spaghetti and meatballs, shared by two stray dogs, might be adorable in animation, but in real life, it would be a mess of slobber, fur, and questionable sanitation. Not to mention, trying to recreate this scene on a date could result in an awkward, sauce-covered disaster rather than a magical moment. This is something to keep in mind for those who engage in casual dating for adults, where an unplanned messy meal might not set the best first impression.
4. The Snake Mishap – Indiana Jones and the Temple of Doom (1984)
What’s worse than a bad date? A meal of eyeball soup, live eels, and giant beetles. Indiana Jones (Harrison Ford) and Willie Scott (Kate Capshaw) endure one of the most stomach-churning dinner scenes ever as they dine with a foreign dignitary. This is not exactly the candlelit dinner of romance—it’s nightmare fuel. Watching Willie squirm at the bizarre menu makes us all grateful for normal dinner dates.
5. The Rollerblading Date – Norbit (2007)
Norbit (Eddie Murphy) and Rasputia’s (also Eddie Murphy) rollerblading date is an absolute catastrophe. Rasputia, an overbearing and aggressive partner, steamrolls through the date, leading to awkwardness, injuries, and sheer chaos. It’s a masterclass in how to make your date as uncomfortable as possible. The slapstick nature of the scene makes it hilariously bad, but undeniably one of the worst dates ever.
6. The Vomit-Inducing Dinner – Bridesmaids (2011)
Nothing ruins romance like food poisoning. Annie (Kristen Wiig) and her fellow bridesmaids endure one of the most gruesome dining experiences ever when a fancy Brazilian restaurant gives them all severe food poisoning—right before they try on wedding dresses. The scene is more horror than romance, with characters vomiting and suffering from explosive diarrhea. If there’s one thing to avoid on a date, it’s a meal that makes you fight for your dignity.
7. The Explosive Dessert – Mrs. Doubtfire (1993)
Daniel Hillard (Robin Williams), disguised as Mrs. Doubtfire, attempts to sabotage his ex-wife’s date with her suave new boyfriend (Pierce Brosnan). The result? A sneaky addition of pepper to his dish, leading to a dramatic choking scene that nearly ends in disaster. Nothing like a near-death experience to kill the mood. It’s hilarious for viewers but a total disaster for the characters involved.
8. The Brutally Honest Dinner – 500 Days of Summer (2009)
Tom (Joseph Gordon-Levitt) goes on a date to try and move on from Summer (Zooey Deschanel), but it quickly turns into a sad, awkward disaster. His lack of interest is painfully obvious, and when his date asks if he’s okay, he straight-up says, “No.” Yikes. There’s no coming back from that level of honesty. Sometimes, it’s best to fake a smile and power through.
9. The Singing Waiters – My Best Friend’s Wedding (1997)
Julianne (Julia Roberts) is on a mission to ruin her best friend’s wedding, and in doing so, she orchestrates a nightmare of a lunch date. What was meant to be a simple meal turns into an over-the-top, cringe-worthy musical number as an entire restaurant bursts into song. A bad date for Michael (Dermot Mulroney) and an even worse moment for Julianne’s plan. If your date ever ends in an impromptu musical, it’s probably a sign to run.
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10. The Nightmare Double Date – Meet the Parents (2000)
Greg (Ben Stiller) is already in over his head trying to impress his girlfriend’s parents, but a dinner with the family turns into a total disaster. Between awkward conversations, accidental cat-milking discussions, and an urn-breaking fiasco, Greg’s date night is a string of unfortunate, humiliating events. If you think meeting the parents is nerve-wracking, just be glad your date night doesn’t involve accidentally setting the house on fire.
Final Thoughts
Cinema has given us some of the most magical love stories, but it has also delivered some truly awful dates that remind us how messy romance can be. Whether it’s an embarrassing moment, a culinary catastrophe, or a full-blown disaster, these scenes prove that sometimes, love is best enjoyed with a side of secondhand embarrassment.
