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“The Look On Her Face Was Priceless”: 24 Of The Most Horrible Dates Witnessed By Restaurant Staff
CuriositiesAUG 18, 2025

“The Look On Her Face Was Priceless”: 24 Of The Most Horrible Dates Witnessed By Restaurant Staff

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When a date is going poorly, the number one thing we want is for it to end, not to play out the inevitable conclusion in front of spectators. But if the meeting is set to take place in public, certain obligations might not allow us to run away.
A Reddit user who goes by the nickname Common-Sprinkles9328 recently asked all the waiters on the platform to describe the tables they served where love went to die—and they delivered. Here are some of the most painfully awkward and hilariously disastrous dates they had to witness... because someone had to bring the bread while the night crumbled.

#21

Couple sitting silently at a restaurant table, capturing a tense moment during one of the most horrible dates witnessed by staff.
Girl was actively on a dating app during the date and I felt like she wasn’t being very discreet. A dude once tipped me $100 to give a drink to a woman at another table and he was there with his wife. Life is wild.
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#22

A couple on a date at a restaurant, reviewing menus and sharing a moment, captured by restaurant staff during a horrible date.
Man tried to order for his date, she didn’t like that but it was early in the date so she said nothing, he ordered an expensive appetizer that she didn’t want, only he ate it. She looked not impressed but still seemed to be trying to feign interest. Came time to order dinner and he tried to order for her, something expensive, surf and turf. She said no thank you, she was a vegetarian (something established before the date) and wanted the vegetarian dish. He didn’t back down and insisted she have the surf and turf. She again said no, she wouldn’t eat it. He countered with “he could afford it so why not?!”
She left.

Edit for more info: the vegetarian meal was written down but there wasn’t an opportunity to put the order in.

2nd edit: alright, fine; I was that woman on the date, I never said I wasn’t but maybe I sort of lied for internet points and to also relay to women it’s okay to say no and walk away, even if they pay for things or insist on it. Yes, at the time I was a bartender/server; and yes what happened to me is 100% accurate, I was just the woman and the waitress responded exactly how I described it. Also I left a tip just in case he didn’t and thanked her on my way out.
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#23

Close-up of a woman’s hand with a ring holding a spoon next to a cup, evoking horrible dates witnessed by restaurant staff.
A woman was engaged/married with a ring on her finger and thought she was meeting someone for a networking HH but the guy thought they were on a date.
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#24

A woman and man in a restaurant bar having a conversation, capturing the look on her face during a horrible date.
Rich, well-known, middle-aged business owner brought in a smoking hot young 20 something, and she only wanted to talk to me (also 20 something waiter).

Needless to say, he didn't leave me a good tip.


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Asli Akalin
Asli AkalinBoredPanda Staff