Waiters and Waitresses From Around the World Describe the Most Awkward Date They Have Ever Witnessed

By Landon Wexler
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Photo Courtesy: StockSnap/Pixabay

Love at first sight, epic marriage proposals, five-star meals and witty conversations — some dates go like that. But other people end up on dates that are plain awkward. If they’re lucky, only the server is there to witness their failure.

That doesn’t mean no one will ever hear about it, though. Waitresses and waiters from around the world have come forward with their stories about cringe-worthy dates at their restaurants. From dating site pics that don’t look at all like the person across the table to date-breaking appearances from an ex, they’ve seen it all and are willing to share.

The Worst Proposal Ever Set to Music

I work at a dinner theater, and we do a thing where we set up a fake random draw. The ‘winner’ comes up on the stage to win their prize and is then surprised by their partner, who proposes. It’s usually sweet and makes everybody in the room all fuzzy and warm.

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Photo Courtesy: Simon Maennling/Unsplash

This one guy wanted to take it further and requested to perform a song — he brought his own music and everything. We’re pretty easygoing at this job, so we agree to let him do it.

We do the fake draw, the woman comes up on stage in front of a room of 400 people, and the music starts to play. Apparently, this guy was a little nervous, and he compensated by having a few beverages. What followed was a sloppy performance of a song written by this that seemed to focus on how he was sorry for cheating on this woman with her sister, and at the end of it, he got down on one knee and proposed. Usually, this gets a round of applause, encouraging the person to say yes, but not after that train-wreck of a performance. The poor woman was just holding her face the entire time and starting shaking her head. She replied, “No, what’s wrong with you?”

When Your Girlfriend, the Server, Ruins Your Date

Had a couple come in one night and everything seemed to be going fine. We just hired a new server who I was training, and I asked her if she had any questions. She was still nervous about greeting tables, so I told her she could shadow me and watch what I do. We go over to the couple’s table, and all I hear from the new server is “YOU ABSOLUTE JERK! I KNEW YOU WERE CHEATING ON ME!”

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Photo Courtesy: Steffen Kastner/Unsplash

Turns out the guy was her boyfriend on a date with his side girl, and he didn’t know that she'd just gotten a job there. She didn’t get fired for what she said.

Bad Date or Sign Language Barrier?

Served a deaf couple having a fight. They went from both of them signing furiously to her crying and signalling to me for a stack of napkins for, I assumed, her tears. She whiped out a pen and started writing paragraph after paragraph angrily. It was awkward because I kept having to come back to the table since they ordered multiple courses, and he was just eating and signing while she was hunched over the table writing away while crying. When they finally left, they tipped me pretty well, though, so I guess it wasn’t too bad?

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My Husband Will Be My Date for a Change

In law school, I always worked the Sunday morning shift at the restaurant in town, and it was always so dead, but I’d bring homework so it was mostly okay. Every other week, this couple would come in and order G and Ts and nachos and sit for hours talking about how attracted they were to each other, their intimate life, and would joke about sneaking around and whatnot.

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Photo Courtesy: Alban MartelUnsplash

I never thought much of it until one day when I walked into the dining room from the kitchen and saw the lady had already been seated in a booth facing me. Her dude’s bald head was across from her, facing away from me.

I approached the table, about to ask the lovebirds if they wanted their usual when the dude turned around and IT WAS A DIFFERENT DUDE. The lady looked at me sheepishly as he mentioned to me it was his WIFE’S birthday and they had never been at my restaurant before.

As Long as They Were Consenting Adults

Slightly shorter than a normal guy, maybe 5 foot 4, 120 pounds comes in with a gigantic woman, probably 6 feet tall and easily 300 pounds. Both tatted the heck up with piercings to match.

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Photo Courtesy: Eaters Collective/Unsplash

The woman orders her dish, and before I get the guy’s order, he says in a suave voice, “I think you want more than that.” She smirks at him, says, “You know I do,” and orders three more entrees. This was clearly a thing for them. They seemed incredibly happy together and became regulars at my restaurant.

I feel like I played a not insignificant role in this bizarre couple’s eating fetish for like three years.

Interruptions Can Be Awkwardly Interesting

I had a mid-40s man with a young and attractive mid-20s woman sitting at the bar. They were engaging in small talk and ordering drinks, nothing out of the ordinary. After possibly 45 minutes, a lady stormed into the bar and immediately went up to them. She grabbed the man by the shoulder and said, “You ... You’re a butt,” and walked out. The man turned to his perceived date and said, “Yeah, she does that,” and then left the room, leaving his date to sit there staring blankly into oblivion until she left. Odd.

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Three’s a Crowd

A girl brought two Tinder dates and played them off each other game-show style. They seemed to be unaware that this was what would happen. Splitting the bill was hilarious.

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Photo Courtesy: Jessica Felicio/Unsplash

But Was Your Ex a Good Tipper?

I was a bartender and waiter a few years back, and I was delivering some food to a table to find out that it was my ex and her new boyfriend sitting at the table. We had only stopped seeing each other a month earlier, so it was incredibly awkward for everyone.

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Photo Courtesy: Joel Herzog/Unsplash

The Not-So-Funny Valentine

Working at a restaurant on Valentine’s Day, a girl gave me her number with her boyfriend in the bathroom. I came back and had to deal with her being sweet to him and nice the rest of the dinner. I did not call or text her. It just was weird every time she’d look me in the eyes following.

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Photo Courtesy: Damon Lam/Unsplash
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There’s Always the Bathroom Window

There was a couple sitting at the bar together — seemed like it was the first date. Maybe after 30 minutes of them being together, I’m in the back rolling silverware, and 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.

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We were all flummoxed. The girl sat at the bar alone for at least another 45 minutes before she left.

Buying Dinner and Then Bolting

I was like 19 at the time, very awkward myself, and these two grown ladies in their late 30s came in. One of the women approached me and explained that she wanted to pay and leave without the other woman knowing. And she did. She even said the date wasn’t good for her. But like… Her date sat there for a long time waiting for her to come back, and eventually I went and awkwardly told her “Hey… So your meal is paid for and you can leave if you want.” She seemed surprised, but she didn’t take it too terribly.

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Photo Courtesy: Henrique Félix/Unsplash

Some Beverages Taste Sudsy After an Hour

A woman in her 50s and a guy in his late 20s or 30s. He was wearing a graphic, Happy Tree Friends shirt and she was in a full fur black coat with a mesh shirt underneath. Straight up gothic Cruella de Vil. They didn’t speak a word to each other except when I came to ask how their meal was going, and they both started complaining that their drink suddenly tasted of soap (even though they’d had the same bottle and glasses since they sat down. Convenient that they start complaining about a free bottle when they’re reaching the end of their old one). Either way, they literally just sat staring at each other in silence the whole meal, then paid, got up, and left. Seriously the strangest date I’d ever seen, and the most on-edge I’d ever felt serving customers.

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At Least the Date With the Staff Went Well

This was just before Tinder and dating apps were a thing. It was a blind date, guy and girl. Guy shows up first and is excited, until he sees his date. She had their mutual friend show him an old photo of her because she had since gained significant weight. You can tell he’s let down, but decides to make the most of it. They order drinks and appetizers. We didn’t even get appetizers out before the guy noped out of the date. He sat at the bar asking us to bring the appetizers to him there. Her weight wasn’t the only thing he was lied to about. Her personality and his clashed so hard the date didn’t last 10 minutes. He hung out well after she left. We (the bar and wait staff) invited him to hang out with us at a bar after work. Ended up being a cool guy.

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Photo Courtesy: Alexsander-777/Pixabay

Don’t Want to Look at You But I Am Hungry

Looked like it was a married couple, and at one point, I heard the husband mention he wanted to get a divorce. The next time I came around, the wife had turned her chair around, facing away from the table with her plate in her lap. She asked me for the bill while the husband was desperately trying to get her to turn back around and talk to him without causing a scene.

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Photo Courtesy: Yoal Desurmont/Unsplash

Couple’s Massage for Strangers

I was a bartender and helped get two strangers (man and woman) chatting across the bar. They hit it off and talked a lot, clearly into each other. They moved closer, and I turned away while helping other customers and not paying much notice. Eventually, I realize that he was now standing behind her with his hands up the back of her shirt, giving her a sensual back rub while her eyes were closed, and she was moaning softly. This was at lunchtime.

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It went great for them, but it was awkward as heck for everyone else in the bar.

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The One With the Driest Eyes Pays the Bill

A couple had a rough breakup where both parties wanted to dramatically storm off from an outdoor table. I had to chase them down and run the woman’s card as she was crying on the sidewalk because he wouldn’t come back to pay the bill.

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Photo Courtesy: Tom Pumford/Unsplash

An Ultimatum Led To Lobster For One

At the higher-end place I worked at, this guy pulls in the lot in a new high-end BMW. Flashy guy — chains on, sunglasses inside type. Girl comes in with him, she’s classy. He walks to a corner table, she walks past him, says she wants this booth over here. He’s not budging. Says if she wants to eat with him, it’s gonna be at this table. Well, that doesn’t fly well. They end up leaving, he tells me to hold that table, he’ll be back in a few. Drops her off somewhere and comes back 20 minutes later and has steak and lobster for one.

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Photo Courtesy: Katarzyna Pracuch/Unsplash

The Beverage That Broke the Mood

A couple (luckily not in my section) were clearly on a first date. She ordered a drink and he ordered a beer. The guy's drink was meant to be served in a branded glass, but the only clean ones had just come out of the dishwasher. The waitress gave him one of these glasses, and it must have warm still. She put the glass on the table and poured about half of the very cold drink into it — didn’t even tilt the glass!

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Photo Courtesy: Jony Ariadi/Unsplash

This poor guy picked up the glass, but the temperature difference made the bottom of the glass sheer off. So his whole glass of drink dropped straight down onto his lap.

Obviously, the waitress and manager were all over him trying to help, but they couldn’t exactly take his trousers and give him dry ones. So he spent the rest of his date soaked through and stinking of his drink. They didn’t order starters or desserts, just had a main and left.

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A Free Drink Did Not Make Up for This Guy

A was working at a hotel breakfast restaurant where a conference attendee, who had showed up to breakfast solo and inebriated for about three days by this point, came down with a beautiful woman on his arm that I had seen him bring in the night before. He greeted me, in front of a crowd of guests, with, “Hey! Have you met my date? She’s a paid date! But isn’t she so pretty? I’m trying to convince her she doesn’t need to be one!”

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Photo Courtesy: Wendy Aros-Routman/Unsplash

She ate in miserable silence while he told the entire wait staff over and over about his beautiful paid date. I gave her a free drink.

Maybe He Should Eat Out With Her Sister, Too

I was running food to a table, and as I got to said table, I started to say, “Okay, who has the chicken?” Before I could finish, all I heard was, “Well then maybe you shouldn’t have been with my sister.” Then they both looked at me and I at them. Longest five seconds of my life. I just kindly set the plates down and allowed them to sort out who had what.

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Helping Quiet Couples Converse

During college, I waited tables in a 100-seat formal kosher restaurant where a lot of Hasidic (very orthodox) Jewish blind dates happened. Some of the dates were so socially awkward that they would often sit all dressed up in their finest while in near silence over their meals. Being an extrovert, I would frequently check on them and intentionally interject something silly or interesting (while asking for their next order detail, refilling water, busing plates, etc.) in hopes it would give them something new to talk about (even if it was of them making fun of me during my absence). It often worked, and I got many a better tip from smiling couples to prove it.

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A Piratical Pause In Conversation

I had a young (early 20s) couple come in on what had to have been a first date. You could tell the guy was into her because of the level of eye contact and focus he was putting into listening to her.

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So I’m wiping down the table next to them, and she asks him, “Have you done anything fun this summer?”

He says, “Yeah, I just got back from a cruise”

She responds, “Oh I could never go on a cruise; I’m too afraid of pirates.”

I glance at her to see if maybe it was a joke, but she’s serious. He’s got a confused look on his face but eventually says, “Oh yeah, I get that.”

No Wonder He Never Brings Mom Here

Had a middle-aged couple come into the restaurant, and they were sat in the section right next to mine. They had been there about an hour when a young woman in her 20s and a few friends were sat in my own section. They were only there for about 30 minutes, and when I came to check on the table, one of the girls was crying and her friends immediately asked for the check.

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When they left, I found out that the guy in the middle-aged couple was her dad, but the woman he was with was not her mom. He got caught cheating by his daughter, and while I was in the kitchen she had seen him and confronted him.

Finish Your Dinner, I’ll Move Your Stuff for You

This was a very busy night in a high-end, modern restaurant in Scottsdale, Arizona. A couple sitting on the patio got in a really bad fight, and he took off, while she sat there crying. Well, then the dude drove right up to the fence near their table where she was still sobbing and proceeded to start setting her stuff down on the sidewalk next to her. He then took off and just left her there, alone at the table, crying. The awkwardness was so thick, the chef wanted to make a roux out of it.

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Photo Courtesy: Dane Deaner/Unsplash
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He Knew She Was Married When They Walked In

I saw this much older couple come in, and you could tell they were already a little inebriated. It’s normal. Well, these guys weren’t even married. They were “friends” just hanging out … Well, that’s what the girl thought. The lady was like, “Wow Jerry you’re so nice, thanks for taking me out,” and then Jerry started begging her to take her home and leave her HUSBAND, and she’s like, “Oh wow Jerry, I didn’t expect that. I’m sorry but you know I love my husband and blah blah blah.” It was awkward as they finished their dinner and went home.

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Just a Not-So-Friendly Reminder

I saw a guy and a girl going on what seemed like a nice date. They were laughing and playing games with each other, but when the time came for their waiter to get them their check, the girl said, loud enough for several people around to hear, “Separate checks because —" (points finger at the guy) — "I AM NOT YOUR GIRLFRIEND!” This was followed by awkward silence and the the waiter going to go get their check.

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That Time My Date Became Invisible

It’s a couple’s first date at an Irish pub. They are at an outside table getting to know each other. The pleasant conversation seems to be going well. Enter inebriated girl. She’s out of it. Takes a liking to the guy and decides to go over and join their date. Sits at the table slurring, “Heeeey you’re cute,” and proceeds to climb into his lap and try to get cozy with him. Everyone’s watching this slow-motion train wreck. He removes her and gently sets her down (big dude, think he’s a bouncer somewhere) and continues playing attention to his date. She won’t give up, so he pulls the best move ever … buys her a shot, she does it and promptly passes out on the table. They continue their date, completely ignoring the idiot sleeping on their table. Hope they worked out, I’d love to hear them tell their “how I met your mother” story.

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You’re Kind of Hard to Love, But I Do

Couple sitting at a table. Look to be mid 50s. Wife says kinda low-voiced, “I love you,” as the husband is browsing the menu. He looks up kinda grumpy and says, “What?” The wife repeats, “I said I love you.” He doesn’t look up this time and just says “Oh,” in a very disappointed tone. Yikes!

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Photo Courtesy: Alva Pratt/Unsplash

Rude on Arrival

When I was bartending, this average looking guy, late twenties, came into the bar on a weeknight,. He sat down, asked for a drink and told me he was nervous because it was his first date in three years, and they had met on Tinder. He arrived 20 minutes before her expected arrival to get rid of some of his nerves. Two hours passed, and he waited for her with no text or call explaining she would be late.

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This woman walks in, walks up to the guy, and I’m thinking, “Wow! She really came!” She looks at him and says “Are you Joe?” The guy replies yes and gets up to properly greet her, looking incredibly excited. She says, “No thanks …” and just leaves.

What a foul creature. Joe and I proceeded to party it up hard for a Tuesday. Poor average Joe.

When Energy Vampires Go Out on the Town

A couple came into the restaurant dressed very goth. I wasn’t their server, but I was running the cash register just a few feet away. They proclaimed to everyone that they were energy vampires, but not to fear them because they won’t hurt us. They said they didn’t need our food for sustenance, but enjoyed the taste. After ordering the meal, they then politely asked the waitress if she would stick around for a second so they could feed off of her aura and have enough energy for the night. The waitress said okay and gave me a side glance over her shoulder that I knew meant, “I better get a good tip for this.” The couple clasped each other’s hands, closed their eyes, and made sucking sounds for a solid minute before leaning back in the seats and sighing as if they had just had a turkey dinner. The waitress was indeed tipped well for her delicious energy.

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