5 Epic First Date Fails and How to Bounce Back Like a Pro

Man embarrassed on date with woman with open box and question mark icons

There are no two ways about it—first dates sometimes feel like you are trying to defuse a bomb with chopsticks—and you never got the hang of using chopsticks to eat, let alone race against time to disconnect the right wire.

But even when things go hilariously sideways, there’s always a way to save the day—or at least live to date another day. Here are five epic first date fails and our expert advice on turning them into funny stories you’ll hopefully still be laughing about together on your first or tenth anniversary!

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1. The Case of the Exploding Drink

There you are, channeling your inner mixologist to show your date you know a thing or two about fancy cocktails, but your over-enthusiastic hand gestures send your beverage flying across the table. It’s a wet t-shirt contest that nobody signed up for. How do you turn this soggy disaster into a laugh?

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The Fail: You wanted to impress with your knowledge of fancy cocktails. Instead, you gestured too broadly and sent that drink flying across the table, soaking your date in a cocktail they had no plans of wearing.

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The Bounce Back: First, try to resist the urge to beg the heavens you will evaporate due to overwhelming embarrassment, or just get up and leave. Offer your date a napkin and laugh it off with, “Well, I guess I wanted to make sure our first date was unforgettable.” Showing you can handle unexpected situations without praying that you’ll disappear into thin air (and some jokes) can actually score you points. You should also apologize and offer to buy the next round—after all, you are down one beverage.

embarrassed woman

2. The Not-So-Silent but Deadly

Okay so this is my worst fear and I know I’m not alone in this being the thing every dater dreads: your body betrays you with a sound that could scare off small children and startle dogs, right when you were hoping to impress. Can an absolutely mortifying gas leak become the moment that breaks the ice, or will it just break the mood and your will to live?

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The Fail: Nerves get the best of your digestive system, and a sound you hoped would never escape your body in public makes a grand entrance at the worst possible time (which is anytime on a first date).

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The Bounce Back: If they pretend it didn’t happen (bless them), follow their lead. If they snicker and you haven’t already headed for the hills, muster up the courage to join in. A laugh can break the ice. Later on, if you’re feeling super brave, you can make a light-hearted comment to acknowledge the elephant in the room—or, in this case, the sound in the room.


3. The Ex-Files

You accidentally open Pandora’s box of exes, turning a casual chat into a trauma dump therapy session about past loves. Whoopsies! Is there a smooth escape from the clutches of this conversational black hole, or are you already being written off?

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The Fail: Somehow, the lovely conversation you were having took a hard, wrong turn down memory lane, and you found yourself talking about your ex. Like, a lot.

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The Bounce Back: Gently steer the conversation back to the present. “Anyway, that’s enough about the past. I’m really interested in learning more about [something related to your date].” Showing that you’re genuinely interested in them, rather than dwelling on history, can help gloss over the error in judgment.

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4. The Misjudged Joke

You’ve got jokes, huh? There you are, trying to be a comedian and lighten the mood with a joke, but it crashes and burns in a spectacular silence. Is there a way to recover from a comedic catastrophe, or should you signal for the check?

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The Fail: You tried to break the ice with a joke. Unfortunately, it landed with a thud, leaving a silence so awkward you could hear a pin drop in another time zone.

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The Bounce Back: Own up to it with a smile, “Well, that didn’t go as planned. Let me try that again without the comedy.” Sometimes, the self-awareness of acknowledging the flop can be pretty endearing and make up for the unfunny joke.

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5. The Fashion Faux Pas

Either you misread the dress code memo, or your fashion sense was out to lunch when you got ready, but you find yourself getting attention for all of the wrong reasons. Can you style your way out of this?

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The Fail: You either underdressed or overdressed dramatically, making you look, at best, out of place and, at worst, like a lunatic.

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The Bounce Back: Confidently owning your look could just turn a potential fail into a win. “I guess I got a little excited and may have gone overboard with the dress code. Next time, I’ll go for something between PJs and prom.” Humor and confidence can turn even the most embarrassing moments into funny anecdotes.

Final Thoughts on First Date Fails

There’s no doubt about it—first dates can be wildly unpredictable and sometimes disastrous, but it’s how you handle it and, more importantly, the recovery. The ability to laugh at yourself, stay calm in the face of unexpected and even embarrassing events, and still show interest in your date can make even the most cringe-worthy moments turn into fun memories. The best romantic relationships are built on laughter, understanding, and a mutual spoken or unspoken agreement to deal with the occasional awkward moment together.

So the next time your first date takes a downhill run toward disaster like a bunny slope skier who accidentally ended up on an expert diamondback trail, remember these epic fails and know that there is a way to bounce back like a pro and save the date. And you never know—these hilariously awkward moments could be the beginning of a love story you’ll tell your children. “Hey kids, do you know how your mom and I met? She threw a drink on me!”

Molly Davis
Molly Davis

Molly is an East Coast writer who lives on West Coast time. She’s been in the journalism field for over 20 years — newspapers are her first love but she’s finding digital media to be just as fun and challenging as print! When she’s not giving therapist-quality dating advice, she’s curled up watching movies, reading, or volunteering at local dog shelters.