The Worst Dates In History – As Told By The Waiters Who Witnessed Them

We’ve had bad dates aplenty. Who hasn’t? They’re a natural part of the minefield that is the dating landscape. They’re an emotional obstacle course of awkward conversation, bad jokes, nervous laughs, and our finest Oscar-winning trying-to-appear-interested faces. What’s worse is the realization that other people have witnessed and noted our bad dating experiences and taken to this Internet thread to share. No bad date is safe. Here are the worst dates in history according to the waiters and waitresses who witnessed them.

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  “I bring out the cake, the manager follows me with two glasses of champagne” A guy made a reservation saying he was going to propose. He asked for a special table and for dessert to come with a sparkler candle and, "will you marry me?" written on it. I bring out the cake, the manager follows me with two glasses of champagne, my co-workers are cheering. We set everything down and walk away. They end up having a serious, quiet discussion and it is very obvious that she is rejecting the proposal. Then three of their friends show up and sit at the table, all excited thinking their friends just got engaged. But it quickly became apparent to them that it was not the case. It's very quiet and awkward at the table. The woman who was being proposed to left, and the reject and his friends got wasted. He gave me a 20% tip too, which was nice considering how shitty his night had been. [sic] dinosaursroamyourmom   "Nope. Nope. Nope." Couple comes in on Valentines Day - no reservation. They get seated at the bar, order some drinks and apps, and are sitting there chatting and laughing. Seems pretty normal. After finishing their apps, the guy drops to one knee, and pulls out a ring. Girl immediately shuts him down. He didn't so much as get a word out, before she's saying, "Nope. Nope. Nope." Grabs her coat off the back of her chair, and is putting it on, still saying "Nope" over and over. Practically RUNS out of the place, does not look back. He looks gutted. Pays the bill, walks out, staring at the floor the whole time. [sic] malackey    “A 'smoke’” A guy came in with two escorts. He went out for a 'smoke,' and left them with the bill. The police were called. They didn't stick around for obvious reasons. [sic] Jiffypopmonster   “50-year-old Vanilla Ice” I’m pretty sure they met on the Internet and was their first time meeting. The lady was Asian and clearly not fluent in speaking english. The guy was white and reminded me of 50-year-old version of Vanilla Ice. The worst part was when he mocked her english, openly called her ugly and demanded that she pay for his beers. The most heartbreaking thing was that she said she would pay for his beers if he would stop calling her ugly. [sic] Aintnomarktwain   “Not a place with free fry refills” It was a blind date between a man and a woman while I worked at a pizza place. The lady ordered a small pizza and a drink and the guy ordered a plate of fries and a root beer. It was weird to order just fries because this wasn't a place where you did that. What was weirder was when he finished he ordered another plate, and then another and then another. This was not a place with free fry refills. I also refilled his root beer about twenty times. Every time I came back with a new root beer or another plate of fries the woman looked more and more uncomfortable. When all was said and done he ate five plates of fries and enough root beer to float a boat. [sic] Dawnshark   "No. She will not be marrying you." I worked in a "romantic" restaurant. We used to get a lot of Anniversaries, Birthdays, and yes, Proposals. We even offered rose packages. Had a reservation requesting our most special private corner booth for 2, with a dozen roses, for a marriage proposal. When the group arrived, the man sheepishly asked to be moved to a larger table, because his girlfriend's Mother had decided to tag along. The server said it was very uncomfortable the entire time. Well, he decided to go on with it anyway. He pulls out the ring, asks her, and the Mother says, "No. She will not be marrying you." The girlfriend never said a word, just looked down at her plate the entire time. THEN they uncomfortably continued their meal in silence, HE paid for the bill, and the Mom took the daughter home. [sic] captainp42   “I broke his collar bone” I was working as a waitress in a restaurant that saw a lot of upscale business lunches--back in the three martini era. The CEO of one multinational used to come through every few months and spend a couple of days taking people to lunch at the restaurant. He was friendly (and pretty drunk by the end of these four hour+ lunches) and he'd often ask me out on a date. Quite charmingly, which made up for the fact that he was some 40 years older than me. After about two years I said yes to a date. Figured it would be a fun dinner and then I'd disappear, dubious virtue intact. We had a lavish dinner in the rooftop ballroom of the Hotel Vancouver. We enjoyed cocktails, champagne, lobsters, a couple of bottles of red wine and then several rounds of double armagnacs. There was a big band orchestra playing and, despite the fact that I didn't know a thing about ballroom dancing, he got me out on the dance floor several times. I was having a great time and so was he. During the last dance, I decided to try and do the swoop with him in my arms. Did I mention that he was 6' 4"? Over a foot taller than me. I dipped him down and then I dropped him. And then I fell on top of him. I broke his collar bone. We spent the rest of the evening sobering up in the ER. He kept coming back to the restaurant, but he never did ask me out again. [sic] Nolora