Waiters And Waitresses From Around The World Describe The Most Awkward Date They Have Ever Witnessed

Waiters And Waitresses From Around The World Describe The Most Awkward Date They Have Ever Witnessed

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 this failure.

But that doesn't mean no one will ever hear about it. Because 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 the ex or wife, they've seen it all and are willing to share.


45. This Did Not Lead To A Date With Me

A girl hit on me in front of her boyfriend when I was serving. The boyfriend walked off after telling her off and the girl awkwardly sat there alone for a while. I asked a girl server to take over her table because it was too awkward.


44. The Worst Proposal Ever Set To Music

I work at a dinner theatre, and we usually do proposals where we set up a 'random draw' where the 'winner' comes up on the stage to win their prize, and are then surprised by their partner who proposes. It's usually sweet and makes everybody in the room all fuzzy and warm.

This one guy wanted to take it further and requested to perform a song — he brought his own music and everything. We're pretty easy going 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. So what follows is a sloppy performance of a song written by this guy, that seemed to focus on how he was sorry for cheating on this woman with her sister and at the end of it, he gets down on one knee and proposes. 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 starts shaking her head and says "No, what's wrong with you?"


43. Didn't Even Wait For Dessert

The first date, I would estimate college age. They’re eating and the girl says “I’m having a really nice time, but my friend just texted me and asked me if I wanted to hang out, and I said yes, so I actually have to go.”


42. 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 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 WITCH; I KNEW YOU WERE CHEATING ON ME!”

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



41. Should I Put The Summons In The To-Go Box?

I guess you could call this a couple date. I was working at a wine bar when a married couple sat down on a pretty slow night. I went over the specials and they ordered. 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. I did bring out tissues for the wife who was breaking down. I ended up boxing up the dinner. The guy paid but I do not envy that ride home.


40. 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 whips out a pen and starts 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?


39. And The Oscar For Best Server In A Supporting Role Goes To...

One of my first jobs in New York was managing a lounge/cocktail bar in a high-end hotel. At around three or four o'clock, a guy that looked pretty cheesy (slicked back hair, bad suit etc.) came up to me and demanded that he get that window table tonight for his date (he had a reservation for 8 PM). I explained to him that I couldn’t guarantee it, etc. and he slipped me $400 with the “How about now” look, after which I eventually caved in and told him that I’d take care of it.

He then pulled another stack of hundreds and started counting them in front of me while asking if I could go a little extra by coming over to the table when he was there with the date and pretend that I knew him from a movie. At this point, if I’ve gone this far, why not?

Sure enough, he rolled around later in the evening with a blonde woman and after they’d had a glass of champagne I approached the tables around them, checking on how they were doing before going over to him and doing the whole “How are you enjoying your evening?” And before walking off I did an Oscar-worthy double take with an “Are.. are you... by any chance..? You must be..” at which point he had this idiotic smile lapping up the “recognition” he was getting from this young dude he’d just paid off. Most importantly for him though, it worked - she was loving it - and they left shortly after and he slipped me another $600 on the way out.


38. 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 ok. Every other week, this couple would come in and order G&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.

I never thought much of it.

Until one day, 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.


37. 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.

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.


36. 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 storms into the bar, and immediately goes up to them. She grabs the man by the shoulder and says "You..You're a butt," and walks out. The man turns to his perceived date and says "Yeah, she does that," and then left the room, leaving his date to sit there staring blankly into oblivion until she left. Odd.



35. Three's A Crowd

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


34. But Was Your Ex A Good Tipper?

Was a bartender/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.


33. This May Have Started A Much Happier Love Story

When I was waitressing in college, I witnessed the single most embarrassing thing to happen to a person to date.

Right in the middle of their dinner (and in the middle of our Friday night dinner rush), this poor guy stands up, taps his wine glass to get everyone's attention, and then proceeds to tell EVERYONE what a fantastic person his girlfriend is, how much he loves her, and how lucky he is to have her in his life.

The whole time this is happening, she is just sitting there watching him with the most bored look on her face. It was so weird. Kind of like, "Yeah, tell me something I don't know".

Then poor guy pulls out a ring, gets on one knee and asks her to marry him. She gives him the most disgusted look imaginable and says "THIS is the ring you expect me to say yes to? Are you stupid? Could you be any cheaper?" Then she gets up and walks out, leaving the poor guy just kneeling there.

I didn't charge him for the meal.


32. The Not So Funny Valentine

Working at a restaurant on Valentine’s Day, the 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.


31. This Calls For Matching Tuxes At The Wedding

Served a young couple at a high-end Italian restaurant that came in wearing matching outfits. I asked them what the occasion was. They were celebrating their three-month anniversary. I’m so glad they found each other.


30. Or 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.

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



29. Buying Dinner And Then Bolting

I was like 19 at the time, very awkward myself, and these were two grown ladies in their late 30s. One of the women came up to 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.


28. Some Beverages Taste Sudsy After An Hour

A woman in her 50s and a guy in his late 20s/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.


27. Don't Tell Me What To Drink

There's a habit of some older couples where the elderly gentleman will order on behalf of his wife. I guess it might have been cute and romantic once, but it doesn't work with some younger couples.

I was serving a younger couple (early 20s), who seemed pretty early into the relationship. They were ordering drinks and he ordered her drink for her. Far from being dazzled by him knowing what she wanted, she didn't want any of it.

"Well, I'd actually like a latte, not a coke. But fine, whatever, if I don't get a say..."

He responded quite angrily with "Oh sorry, have what you want then!" She got her latte and he glared at me. They ate and left. Not been in since. I'm sure they're doing well.


26. My Favorite Place For Lunch And Breakups

Had a few breakups occur. Those are super awkward. The guy bringing the girl to a public place so she won't cause a scene happens quite often. This one time a guy did this with his girlfriend at lunch. She then starts bawling, I mean WAILING, and everyone around is looking in their direction at this point. She then quickly resorts to anger and then starts yelling at him, tells him to "Have a great life you stupid loser" and whatnot, then proceeds to get out of the booth.

Her foot gets tangled in her long purse strap and she falls and slams her head on the back of the booth corner and falls on the floor. She is now really wailing at this point since 20 people in the restaurant watched her do this and she ends up running out the front door. My coworker goes over to the dude and is like, "Do you want your check?" Since they already ordered the guy was like, "Naw, bring me my food still and just box up hers for me, may as well have some lunch!" He sat there and ate and didn't seem too bothered by what happened. Just a weird situation. You never know how someone is going to react to a breakup in public.


25. 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 ten 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.


24. Forget You Ever Saw Me. Seriously

I had this girl one day on a lunch date (or so I thought) with this other girl. Thought nothing of it, maybe they were together maybe they were not.

Well, I had one of the girls sit in my section again...with another girl. Thinking nothing of it, I ask if she is the same person that I served a few days ago. Her eyes turned giant and the girl she was with laughed nervously, saying, "Oh, you came here without me."

At this point, I caught onto something so I tried to save it by saying it must have been someone else, I get so many people some days. I'll never forget those eyes piercing through my soul telling me to shut up.



23. 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 ticket while the husband was desperately trying to get her to turn back around and talk to him without causing a scene.


22. 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, talk a lot, clearly into each other. They moved closer, I turned away and was helping other customers and not paying much notice. Eventually, I realize that he is now standing behind her with his hands up the back of her shirt, giving her a sensual back rub while her eyes are closed and she's moaning softly. This was at lunchtime.

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


21. 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.


20. 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 says to me 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.


19. 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 very different sort of beverage. The guys 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!).

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.


18. A Free Drink Did Not Make Up For This Guy

A hotel breakfast restaurant where a conference attendee, who had been coming 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!”

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.


17. 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, "Ok, 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.


16. Helping Quiet Couples Converse

During college, I waited tables in a 100-seat formal kosher restaurant where a lot of hassidic (very orthodox) Jewish blind date adult couples would eat. 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) 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.


15. Footsy Fail By The Married Couple

So this very nicely-dressed, 40s couple comes in with their teenage children. They tell me his parents will be joining. So everyone sits down and I notice the husband and wife sit where there is an empty chair between them. Thought it was kinda odd but hey, whatever. Parents arrive, get drink orders. Go back to drop off drinks and take orders, and I'll be darned if he doesn't have his shoes off and she is massaging his feet. In our restaurant. During the lunch rush. So I'm trying not to be grossed out while I'm asking what kind of vegetable everyone wants. So gross.


14. His Daughter Probably Wouldn't Waste A Drink Like That

Older couple was having lunch at our cantina, when a younger woman who I assumed to be their daughter showed up. I was coming to greet her and bring chips and salsa when she suddenly grabbed the man’s frozen drink and threw it in his face while shouting, “If you’re gonna have lunch with your wife then you should stop texting me!”

Needless to say, I had their food made up to go...


13. 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.

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.”


12. I Only Sponsor One Date, Okay?

I had a couple with a 1-year-old skip out on a $30 bill after being very pleasant all lunch. I worked at a restaurant that punished you for walk-outs, so I ate the cost of their dinner out of my own tips.

They came in maybe two weeks later, and got sat with me, again. They immediately recognized who I was, and I greeted them with a big "welcome back." I stood next to them almost all dinner. Like, right next to them, over their shoulder, glaring. Lucky for me, it was a slow night.

So they had a pretty awkward date, yeah.


11. 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 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.

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.


10. Finish Your Dinner, I'll Move Your Stuff For You

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


9. The Valentine's Two For One

I had this lady who would always come in with a different dude; they’d buy her a bucket of drinks and a meal and she’d leave with them.

One Valentine’s Day she came in early with some guy, he bought her drinks and meal, they hung out and then left together.

Two hours later she comes back with a DIFFERENT guy, gets him to pay for her drinks and another meal, they hang out and then leave together. The whole time with the second guy though when I would come check on them (I was the bartender, they sat at my bar) she’d always give me a look like don’t even think about saying anything. And she kind of would give me a knowing smile like yeah, that’s right. Of course, I wouldn’t just throw her under the bus anyway. Not my business.


8. 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.


7. 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.


6. That Time My Date Became Invisible

At an Irish pub. It's a couple's first date. 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.


5. 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!


4. Rude On Arrival

When I was bartending this guy came into the bar on a weeknight, average looking guy, late twenties. He sat down and 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.

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.


3. 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 so they could have enough energy for the night. The waitress said ok 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.


2. He Walked Out, But Not On Purpose

College town - game day, really cute girl with an average-looking dude sit down at a booth. He immediately gets up and heads to the bathroom; he’s obviously inebriated. Instead of returning to the table after leaving the restroom he walks straight out of the restaurant, leaving his date sitting alone. After passing the table several times I hear her trying to give him directions back to the restaurant over the phone.


1. I'm Giving Your Ring Back--To The Bartender

Worked as a bartender during college, a couple comes in and sits at the bar and orders drinks. I give them their drinks and go about my business. All of a sudden she stands up and yells some obscenities at him (I forget what; it was 35 years ago) and takes off her wedding/engagement ring, flings it at him and storms out of the bar.

The ring bounces off his chest and off something else in the bar and lands in our ice bin. I dig around in the ice for a couple of minutes and find the ring and hand it to him. He mumbles thanks, finishes his drink and leaves. Dude was crushed.