Waiters Are Sharing The Most Awkward Dates They’ve Ever Witnessed, And You Thought Your Dates Were Nightmares

All service industry employees and veterans have tales the rest of the world simply would not believe. The types of characters that reside in the kitchen and on the service floor are beyond description and sometimes even comprehension.

Though there are those patrons who are sweet, generous, and enjoyable to talk to, there seem to be far more freakazoids out there, intent on ruining somebody’s day.

Then there are couples. Couples who are clearly on their first date. Couples who take sadistic pleasure in torturing their server. Couples who are fighting, cheating or divorcing. These are their stories. Dun DUN (Law & Order sound effect).

Redditor u/StittDownAndListen recently asked the Reddit community, “Waiters and Waitresses of Reddit, what is the most awkward couple date you have ever witnessed at work?” The responses are bewildering, upsetting, and also somewhat hilarious.


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.”



Had a couple come in one night and everything seemed to be going fine. We just hired a new sever 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 couples table and all I hear from the new server is “YOU F**KING BITCH I KNEW YOU WERE CHEATING ON ME”

Turns out the guy was her bf on a date with his side chick and he didn’t know she just got a job there.

She didn’t get fired for what she said.



Husband and wife fight. Wife cried. Husband got up and threw a pizza slice at her face.



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.



When I was bartending this guy came into the bar on a week night, 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 3 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(not his real name) and I proceeded to get way too drunk for a Tuesday. Poor average Joe.



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.

Not been in since, I’m sure they’re doing well.



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 tasted. 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.



Served a deaf couple having a fight. They went from both of them signing furiously to her crying and signaling 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?



When I was a waitress at Olive Garden, one of my tables was going over their divorce paperwork. When I greeted the table I asked how everyone was and the woman said, “Terrible! We are getting a divorce.”

Like wtf do I say to that?



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 guys brother. Apparently glasses were thrown across the room and they both got kicked out.



Not 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 I worked at 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/tearful and they were bickering about holiday schedules for their daughter/timeshares etc.

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.



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.



They sat down and, 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. The body language shift occurred over maybe 1.5 hours.

He didn’t stop talking the entire time. She did give some nods and “uh huh”‘s in response; even perked up a few times to contribute. But his monologue never stopped.



Date 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.

Toppled his chair backwards 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.



This trashy couple I served were disgusting people to begin with and to top it off the woman was trying to be sneaky and jerk him off under the table. Unfortunately I saw this happening and just pretended like nothing was happening because I didn’t want to deal with it.



Working at a chili’s 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, just was weird every time she’d look me in the eyes following.



This wasn’t so much as awkward but just unusual: 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 3 month anniversary. I’m so glad they found each other.



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 gf 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 retarded? 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.

Edit: Just to clarify, this was a real rejection. 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



There was a couple sitting at the bar together – seemed like it was a first date. Maybe after 30min 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.



I had a couple get in a huge fight while I was waiting on them. I tried to stay away from the table towards the end of the meal because the tension was so high. They were regular customers who I would see come in every few weeks, but I had never waited on them myself.

At one point, the man gets up and starts walking across the restaurant to leave. The woman stands up and screams across a crowded restaurant, “AND YOU MADE ME STICK MY FINGER UP YOUR ASS!!!” I never saw them in the restaurant again after that night.



Was a cocktail waitress at a bar in a high-end restaurant a couple years ago. This couple comes in right around peak hours, guy looks annoyed, 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 drunk and starts hitting on the female bartender and eventually the cocktail 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 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. Made the whole night super awkward and stressful.

Definitely one of the more memorable experiences of that place.



In law school I always worked the Sunday morning shift at the restaurant in town and it was always soooo 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 sex life, and would joke about sneaking around and what not.

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 love birds 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 lmao.



I’ve told this one here before. I worked in a resort hotel, high end, I waited tables in the fine dining restaurant. It was pretty common for people to propose there, so much so that I had a system for the whole thing.

One guy came in and wanted to do the ring in the champagne thing, and I talked him into doing a dessert alternative that doesn’t result in a sticky ring and champagne on the floor. Anyway, long story short.

I bring the ring, she says “Dammit, I’ve told you before I’m not marrying you.” He flips, she’s super calm about it and basically treats him like a child having a tantrum, which to his credit he was not screaming or anything, just very upset.

He left, she ate the fucking dessert, eventually he came back and paid and they left together. Super awkward.