11 Waiters Reveal the Painfully Awkward Dates They Served

From awkward dates, to cheaters, to proposals that bombed, these waiters reveal some of the most awkward couples situations they ever encountered.

Mustafa Gatollari - Author

Nov. 19 2018, Updated 3:16 p.m. ET

harry met sally cover
Source: columbia pictures

Watching an awkward exchange between a couple when you know them is bad enough, but imagine having to go through it when you're hired to wait on them. At least when you're a friend, you can just exit the situation. When your livelihood depends on it, it's literally your job to sit there and bask in the awkwardness.

In this recent AskReddit post, a bunch of people revealed some of the cringiest dates they witnessed while on the job.

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1. "Sorry I slept with your sister, marry me?"

dirty grandpa
Source: lionsgate

One guy who worked at a dinner theater spot allowed someone to come up and sing a song. Typically, people will come up to perform and then, out of nowhere, get down on one knee and propose to their significant other. It's usually a cute, applause-filled affair.

Except this one dude who got a little too tipsy and delivered a "a slurred performance... that seemed to focus on how he was sorry for cheating on this woman with her sister." Naturally, the woman wasn't having any of it and stormed out of the venue. The stage manager could only think to grab the mic and simply say, "Well, that's that."

- AgainstBelief

2. Dinner and divorce?

Source: hbo

When a couple walked into a wine bar for a nice date, the woman was blindsided by the dude serving her divorce papers. "Once appetizers came out the man thought it would be a good idea to serve his wife divorce papers. I did my best to avoid that side of the bar." 

At least the waiter thought to "bring tissues for the wife who was breaking down." He boxed their dinner for them and the two went back home in the same car together. Ouch.

- ThereandBack22

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3. "You didn't look that fat in your pictures."

angry man holding crashed phone picture id
Source: istock

Chalk this one up to a sad consequence of modern romance. A couple comes into a bar, but things don't look right off the bat because the "guy looks annoyed, [but the] girl looks really excited." The dude proceeds to ignore the girl the entire night and starts hitting on different women at the bar, including the bartender. When she finally calls him out for his behavior, he insists that he doesn't want to be there and he's not going to pay for her drinks or meal, but the worst is when "he...tells her that she didn't look fat in her picture and he wouldn't have asked her out if he'd known she was that big." Ouch.

- icysunshine

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4. Deaf couple arguing in sign language.

woman showing thumb down and grimacing at studio shot picture id
Source: istock

It's one thing to walk in on a couple having an argument at a table, and another for it to be a really heated argument. But what about a deaf couple? This waiter saw "them signing furiously" until the woman at the table began "crying and signaling to [the waiter] for a stack of napkins." They stayed for their meal and throughout the whole thing the woman kept crying and writing paragraphs on the napkin. "When they finally left they tipped [the waiter] pretty well."

- midgetT-rex

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5. Escape plan.

escape plan
Source: summit entertainment

This server "notice[d] a gorgeous blonde in her late 20s is sitting with a very well-manicured looking guy in his mid 40s." The dude's dressed to the nines and talking to this young woman, but it's clear she isn't into him at all. It's only a matter of time before "she quickly picks up her phone and frantically calls someone and begs for pickup ASAP" while the banker dude's in the bathroom.

After 15 minutes or so, a man her age comes into the bar and escorts her out, she cites some kind of family emergency. The banker hangs out for a bit, hits on a waitress, gets rejected, then pays his tab in exact change and doesn't leave a tip.

- mesoziocera

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6. Ouch.

divorce relationship problems being single or regret concept serious picture id
Source: istock

A server witnessed a guy stand up in the middle of dinner at a busy restaurant and "proceeds to tell EVERYONE what a fantastic person his gf is, how much he loves her, and how lucky he is to have her in his life," while "she is just sitting there watching him with the most boring look on her face."

After he proposes, "she gives him the most disgusted look imaginable and says 'THIS is the ring you expect me to say yes to? Are you retarded? Could you be any cheaper?'"

After her outburst, she storms out of the restaurant, leaving the dude on his knee on the floor in front of everyone. At least the waiter didn't charge him for his meal.

- Penya23

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7. Food fetish.

its dinner time picture id
Source: istock

One waiter will never forget the first time they saw a "Really little guy, maybe 5 foot 4, 120 pounds come in with a gigantic woman, probably 6 feet tall and easily 300 pounds." Turns out these peeps had a food fetish, and the two of them would talk to each other in deep, sexy voices the whole time as he watched her eat. The waiter added that they seemed really "happy" and had a great relationship in the three years they served them.

- significantmundanity

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8. Glass fight!

trainspotting throwing glass
Source: polygram

This was was simple drama with a pretty violent end: "There was a couple at my work having drinks, girl went to the toilet, came back and admitted that she’d been sleeping with the guy's brother. Apparently glasses were thrown across the room and they both got kicked out."

Thankfully, no one was seriously injured.

- Foxjessie

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9. Back door escape

in through the out door
Source: swan song

A couple walks into a restaurant on what appears to be a first date. 30 minutes was probably all the guy needed to know that he wasn't interested in taking things any further because "the dude comes running into the back and goes, “there’s an exit back here, right?” and proceeds to bolt out of the back door." The girl sat at the bar for another 45 minutes before she finally left.

- HappyLittleTrees17

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10. Never be this guy.

couple rejection of a woman in her first date picture id
Source: istock

This little insight into a date gone wrong is a perfect example of ruining something with potential. At the start of the date, "from the girl's body language, you could tell she was into him. As the date progressed she closed off, then sat pretty much sideways, then was playing on her phone."

In a span of 1 1/2 hours, the dude wouldn't stop talking and didn't let her get a word in edgewise.

- TheStankTank 

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11. New Boo.

waiter dissatisfied with small tip from cafe visitors picture id
Source: istock

What happened to this waiter just seemed like a mean case of an ex trying to get back at their former SO. While he was bringing food to a couple he saw that it was his "ex and her new boyfriend sitting at the table." Since they had only broken up a month before, "it was incredibly awkward for everyone." Yikes.


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