Sometimes dates are just awkward. Whether they're first dates or a couple's 100th time going out together, something spoils the mood for them and everyone around them, including the restaurant staff. These cringy experiences are indelibly marked in the servers' heads, showing them how not to act in their own relationships. Explore these extremely awkward tales of dates gone wrong. Content has been edited for clarity.
He Almost Blew The Customer’s Cover
“In law school, I always worked the Sunday morning shift at the restaurant in town and it was always completely 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 bedroom 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.”
Don’t I Know You?
“I was bartending a day shift at an upscale Italian place in a high-end shopping center over the Christmas season. A couple comes in, starts drinking and is VERY flirty with each other. They clearly liked the attention. I wasn’t quite sure why the man seemed familiar but he had a face I knew from somewhere.
Midway through their lunch, the woman used his name and it dawned on me that the man was the husband of my previous boss. I told him he looked familiar and asked if he was ‘Mark’ from ‘that restaurant on the way to the beach?’
He said that he was not but the woman he was with insistent on making it awkward and peppered me with questions like, ‘I’ve heard the owner of that place is crazy, did you know her?’ She was backhandedly trash-talking ‘Mark’s’ wife and the whole thing was so uncomfortable. He was an all-around bad dude though and deserved it.
For additional context, his family had owned ‘that restaurant on the way to the beach’ and his wife (my former boss) ran the place until she caught him cheating. They divorced, she got the restaurant and continued to run it with her sister.
Fast forward a few years and the two eventually remarry. It was during their second marriage that he turned up at my bar with his mistress.”
Maybe They Should Have Met For Coffee First
“I was a waitress at a bar in a high-end restaurant a couple years ago. This couple comes in right around peak hours, the guy looks annoyed, while the girl looks really excited. The whole time the girl is trying to talk to this guy and he’s completely ignoring her. He gets a call and talks on the phone for a good 10 minutes, hangs up and starts talking to anyone around him but her. He’s getting more and more wasted and starts hitting on the female bartender and eventually the waitresses (myself included), telling us he could get us all much better jobs in Atlanta.
The girl he’s on a date with has started crying at this point and once he actually notices, he yells at the bartender because it was obviously the restaurant’s fault for her being upset. She yells at him to stop yelling at the bartender because he’s been such an awful date and he goes off, tells her he didn’t even want to eat here, she should’ve picked a better place, and he isn’t paying for her food and drinks. He then 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 (probably met online kind of thing).
She retreats to the bathroom and the guy continues to make a scene. Another girl at the bar and I go to check on her while the bartenders and manager try to deal with him. The girl is super upset and I tell her there’s a back door she can leave through and I can get her tab from the bartender. I go back out and the guy had already stormed out and refused to pay, leaving his date with a nearly $200 check. She didn’t have the money to pay so a couple of the bar regulars covered it. It made the whole night super awkward and stressful. Definitely one of the more memorable experiences of that place.”
Perhaps The Lady Would Like…
“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 orders 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. They have not been in since but I’m sure they’re doing well.”
Olive Garden Isn’t The Best Place For Romance
“A guy proposed to his girlfriend at the booth across from my friends and me…at Olive Garden. When he got down on one knee and opened the box, she was shaking her head and then just stared silently. It must’ve been a whole 30 seconds of pure silence, but it felt like an eternity. Then, the guy proceeded to describe the ring, how much it cost, the different aspects of it, etc. Finally, the girl just went, ‘Nooooooo’ and the guy just sat back down and they tried to finish their dinner. I caught eyes with our server and he made the most perfect ‘holy heck, that was bad’ face. Geez, that was awkward.
I still picture him saying, ‘My love for you is like these breadsticks…Unlimited.’ He didn’t say it, but I still picture it.
I really don’t think she rejected him because of the location. Obviously, I can’t be certain, but she seemed like a nice girl and had this, ‘What’re you doing? You hardly even know me,’ expression on her face.”
The Bagged Salad Really Triggered Her
“I waited tables at the Olive Garden 10 years ago. A guy and his wife sat down at a table and immediately started arguing. Something about his affair and how a baby from it was costing them money. Finally, it culminated as I was bringing out their salad. As I walked away I heard the wife say:
‘Well, maybe if you hadn’t boned our son’s girlfriend and gotten her pregnant, we could afford to eat somewhere nicer than the goshdarn Olive Garden. Oh look, the highlight of my meals: Unlimited. Bagged. Salad. Maybe you could save up and we could go to Joe’s Crab Shack for our anniversary. Miserable man.'”
Let’s Go Out…To Negotiate
“It wasn’t exactly a date, but I served a couple one time who had met up to discuss the terms of their divorce at the fancy-ish restaurant where I worked at the time. They came before the dinner rush so they were pretty much my only table, and every time I’d check in on them, the wife was extremely angry and tearful and they were bickering about holiday schedules for their daughter, timeshares, or other issues.
It wasn’t the end of the world but it was extremely awkward to butt in to change our their forks or refill drinks while they were so emotionally charged.”
Someone Loves Himself
“I worked at an ice cream parlor, it’s kinda old-timey. There isn’t too much seating. Anyway, this guy comes in with a girl, they pay for their own cones and take a seat at two of the seven stools. The dude is talking and the girl is laughing and into it.
TWO HOURS LATER, THE DUDE IS STILL TALKING and the girl looks like she wants to cry or punch him in the face. They withstood the galeforce trauma of at least seven families with screaming kids, adults who ‘just love that these tiny places still exist!’ They also stuck around past several rounds of me sweeping around their feet and pointedly scrubbing the counter around them. The guy never asked her a question. Never let her say more than a few words before he stomped out her ‘rude interruptions.’
I eventually said, ‘Hey guys, we close soon. I hope you have a nice day, but I need to mop.’ We still had a few hours but I wasn’t just gonna listen to some idiot prattle on about himself if I didn’t have to. I watched them walk down the street and he was STILL TALKING. Like, get a room with yourself, guy. You’re obviously the man of your dreams.”
So That’s Why Men Break Up In Public
“I’ve had a few breakups occur where I work. 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– and 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 awful loser’ and whatnot then proceeds to get out of the booth and her foot got 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 co-worker 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.”
A Difficult Rejection
“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 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 boring 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.
Not only had they not even finished their meal when he proposed, a hostess at the restaurant knew the guy personally. Apparently, it took him a really long time to get over it.”
Looking For The Next One
“I had a middle-aged couple who seemed perfectly nice. The man asked me where he could go to smoke. I pointed him in the right direction and then started heading back to the kitchen which was in the same direction. He followed me and told me that the woman with him was his ex-wife. Not knowing how to respond, I said it was nice that they got along so well. He told me she just pretended to seem nice and was actually a terrible person.
I was feeling uncomfortable enough, but then he started to ask my age, if I had a boyfriend, what I was doing later. Thankfully, I could excuse myself to the kitchen. However, serving that table was awkward after that especially since she kept touching and complimenting him.
At the time, I was only 20-years-old and he was probably 50-60. While it’s not that abnormal for older men to hit on servers, it still creeps me out every time, making me feel super uncomfortable.”
A Surprising First Date
“Once had a blind date while I was working at an upscale Italian restaurant. The lady came in early, younger and a little on the heavy side to put it nicely. She ordered a mixed drink and almost chugged it, she drank it so fast.
About twenty minutes went by and I’m worried she is going to be stood up. Finally, a guy came rolling in, in a very quick manner like he knew he was late. He was tall and fit and didn’t look like he has trouble finding dates. I was a little worried that he won’t find the nice young lady suitable. But boy, how I was wrong and stupid for thinking these things.
They hit it off, talking and laughing all night. They pretty much closed the place but weren’t being rude or staying too late after we closed. They eventually worked their way out the door. And here comes the kicker: when I went to take some trash outside to the can, I caught them sucking each other’s faces like there was no tomorrow in the lot, propped up on one of their cars. I went inside to share the news with the staff that the date was a success; they were feeling the same way I was about the whole thing. We were all excited, too.
I figured they went home and shagged it out. Anyway, about thirty minutes went by and the waitstaff and I were leaving through the back door. WHAT DO WE SEE? The car they were kissing against was now fogged up and bouncing up and down in our parking lot. It was the funniest way this night could have ended. Moral of the story: don’t put judgments on people’s looks, and always try to shag on the first date.”
How An Aquarium Tore This Couple Apart
“I waited tables at this restaurant that had a big aquarium in the center. Like floor to ceiling huge.
A mixed age couple comes in and they’re nice but the guy is super quiet and nervous. Orders a McCallan straight but you can tell he really doesn’t drink, maybe sipped it twice. His date was probably 20 years younger and she seemed like she liked to party. She ordered two shots of Patron right from the start and took them both.
Another younger couple was sat next to them and staring at the aquarium. Part of the deal there was having to talk about the aquarium and fish while people ordered. If I was busy, I’d try to spiel two tables at once with the aqua script, then make a few jokes and leave.
I got both couples interested and talking then told them both I would be back. After I dropped the apps for both tables, I see the young girl still talking with the younger table and they decide to push the tables together and eat.
The whole time, the older guy is just smiling but I could tell he doesn’t feel comfortable. He barely touched his food and was just a fly on the wall at his own table. Eventually, they decide to take the party outside to do some dancing. During the summer they give free salsa lessons and people have drinks and dance.
Maybe an hour later, I’m taking a smoke break and I spot dude sitting on a bench crying. I walk up to him and give him a smoke and try to talk to him.
Apparently, his wife died about two years ago and that was his first time out since. He said he met that girl on some website and how she reminded him of her but she’s nothing alike and a bunch of really sad stuff. He said the girl left with that couple to go drinking and she just took off and left him alone.”
THAT’S How You Impress A Lady
“One of my first jobs in New York was managing a lounge in a high-end hotel. At around 3 or 4 pm, 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 can’t guarantee it and he slipped me $400 with the ‘How about now’ look in 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 bimbo and after they’d had a glass of bubbly, I approached the tables around them, checked on how they were doing before going over to him and did the whole ‘How are you enjoying your evening?’ And before walking off I did an Oscar-worthy double take with a ‘Are… are you… by any chance..? You must be…’ at which point he had this douchy 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. It wasn’t awkward for them, just for me and all the rest of the waitstaff watching.”
His Nervous Tick Landed Him In The Hospital
“The date initially seemed going well, but the guy was nervous and fidgety. He was rocking back on his chair a little as he would talk and eventually flew too close to the sun. He toppled his chair backward and knocked himself out cold. And peed his pants.
He had to be taken out of the dining room on a stretcher over the span of 20 minutes, while his Tinder date did the honorable thing and immediately went to the bar and ordered shots.
We gave them to her on the house.”
When Being Courteous Gets Rude
“I worked as a cashier at a self-service cafe. The cashier counter is in between two big glass display racks displaying desserts and whatnot for sale on either side. I was taking their orders (mind you, there were more customers behind them) when they started fighting on who was going to get the bill.
They both started shoving cash at me past the counter when a $20 belonging to the girl fell in between the counter and the display rack. It was a really tight spot and neither of us could reach. The display rack is also really heavy and big. She then proceeded to ask me to get a knife and many other random things to get her $20. The worst part was the other customers were clearly impatient. Honestly, as a cashier, I’ve witnessed couples fight for the bill many times, but there’s no need to be aggressive, especially when it involves a third party like a cashier.”
“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 wouldn’t hurt us.
They said they didn’t need our food for sustenance, but they 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.”
“There was this really little guy, maybe 5 foot 4, 120 pounds comes in with a gigantic woman, probably 6 feet tall and easily 300 pounds. They both had a ton of tattoos with piercings to match.
The woman orders her dish and before I get the guy’s order, he says in a sensual 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.”