48 Waiters Share The Most Cringeworthy Dates Theyve Ever Witnessed

1. Death By Hot Sauce

I worked in a restaurant that had a huge selection (150+)of hot sauces. We sold them by the bottle but customers could sample any of them and use them on their food. A couple came in, the guy started bragging about how much he loved hot sauce and how he never found one that was too hot. He asked for the hottest one we have. I brought the bottle to his table, he filled a spoon with the sauce and made a big production of how he was going to eat it. I told him not to, the hostess told him not to, the waitress serving the next table told him not to… he put it in his mouth, started choking and gagging, puked on the table then passed out and did a faceplant right into the puke!! We called 911. He woke up right away and kept gagging for a while. He refused treatment when the paramedics showed up. They left without even ordering a meal! The girl told one of the restaurant staff that it was their first date.

2. Unwelcome News

This lady came in for lunch and let me know she was waiting for someone. When her lunch date got there I took his drink order, grabbed his coke and brought it to the table. As I’m placing it down I see a positive pregnancy test in a ziploc on the table in front of the dude. Her excited face, his shocked, semi-disgusted but trying to look happy face, my what the actual fuck face.

Awkward level went up 100%. I murmured something about congratulations and left the table as fast as I could.

3. Calling Mommy

A couple came into the chain restaurant I worked at. Both looked like they were mid 30s. I go to take the order and the guys says “hold on, let me call my mom. She can tell me what I would like better.” The lady just looked at him like “I messed up..I messed up real bad.

4. The Dine And Dasher

Not worst date, but worst guy on a date. He tried to skip out on the check. I chased him outside and politely asked him and his date to go back in the restaurant so we can solve the “missing money” case. After a fair amount of back and forth and a bunch of bullshit excuses he pulls the bill and the cash out of his pocket, stuffs it into my hand and said, “just take it, man”. At the culmination of this douchebaggery his date’s eyes were as wide as the dinner plates they just ate from.

5. A Failed Proposal

I’m a server at a fine dining restaurant that has a “romantic”, “date-night” setting. most tables are couples celebrating birthdays/anniversaries, etc. But we also see a lot of wedding proposals…about a year ago, a young, attractive couple comes in and asks to be sat in one of our private booths. they are super cosy/cuddly, not in a gross PDA way, just a comfortable “we’re in love” vibe. A few minutes later, the guy sneaks away to let me know that he is proposing at the end of the meal, and if I can do something special to help make the night memorable.

Fast forward 2 hours. Entree is finished. Drop off the desert menu. Say some subtle phrase, like, “I’ll give you two a few minutes to look through the dessert menu…” aka “it’s go-time.”

A few minutes later, I’m standing around the corner from their booth holding two champagne flutes, chocolate dipped strawberries on a plate covered in rose petals, and a digital camera to take a picture to put in the frame that i bought them, free of charge… you know, to help make the moment memorable. They were my last table, and they had been cool the whole night, so i decide to be extra generous and help them celebrate getting engaged. I come around the corner with all my gifts. See an open ring box. Say “congratulations!” Hand them champagne. notice they are both bawling. (aww, tears of joy!) even he was crying, which seemed cute and sentimental. I start snapping some pictures, going for that candid in-the-moment feel. She says something like “I’m a mess. I’m sorry!” sort of awkward laughing, and I say “no, you look great! you’ll want to remember this moment!” and they both stare at me for one last picture. Then, since girls LOVE showing off their new engagement rings, I ask to see her ring….and she DECLINES.

It took me about half a second to snap out of the “yay for you guys!!” mode, and then i get it. Notice the body language. They aren’t sitting side by side anymore. Notice how speechless and awkward they both are. Look a little more closely, and oh wait maybe those AREN’T tears of joy… my brain caught up with what was going on, aaaand I bolted. I dropped off the check and cashed them out…and left them with the framed photograph of a beautiful candid shot of two mortified people, taken moments after a failed marriage proposal, that I then helped make 10x more awkward by forcing them to celebrate it.

6. Random Violence

One Summer I worked at Cheddar’s. A couple in probably their late 40s walked in and sat at one of the high top tables in the bar area. The man ordered a shot of whiskey and a beer, the woman a diet coke. When the drinks come he takes the shot, takes a pull on his beer, and backhands his SO so hard she fell out of her chair. He just sat there calmly drinking his beer until his arresting officer arrived.

7. He Ordered For Her

Couple sits down at my table. Do the usual greeting. Ask them if they would like to start out with a beverage. The female replies, “coke, please”. The male stops her, interrupting “uh, make that a diet coke. I’ll take a jack and coke”. The date didn’t get any better.

8. The One Night Stand

The worst I’ve served by far. I worked at a breakfast place so we got a lot of one night stands awkwardly making small talk, but that was mostly just funny. I became really good at figuring out how far into a relationship a couple was. Anyway, this pair. They came in and sat themselves (we had a host) and then the dude asked to switch tables. You chose that one, though! Anyway, he orders the drinks. One water with extra lemon for the gentleman, two small orange juices for the lady, even though I explained it would be cheaper to get a large, but he declined. When I went back, he asked for more sugar and lemons. He had used all twelve-fifteen packets of sugar (and sweet n low, and cane sugar, and equal) in his water with extra lemon. Their food order was insane. Every ticket I took at that place usually cost about $5-10 per person, and this guy’s ticket was at around $30. His girlfriend’s was $8, including the OJs. Time comes to pay and he stares at the girlfriend. She pulls out a card, which comes back declined. She starts crying when he says he doesn’t have money. She goes outside, calls her mom, calls her bank, whoever. She’s screaming on the phone for about twenty minutes. While she’s melting down outside, dude comes up to the register and throws down a wad of ones. “Here.” And leaves.

9.The Nervous And Sweaty Guy

First date for a couple in their late 20’s. Started smoothly, the obvious first date jitters and awkwardness but nothing odd.

Ten minutes later they order and the guy is sweating bullets, really nervous.I checked on them about 5 minutes later and he’s looking distinctly off.

He didn’t make it to 20 minutes. He shat himself and ran out leaving the girl sitting there in shock and pretty upset.

The story was she had been set up on the date by a friend, who’d told her that he was nice, but extremely shy and nervous. Apparently it was all good until he needed to talk about himself, then shit city occurred. That chair went straight to the dumpster.

10. No Way To Ignore This

A couple in their late 20s was having a quiet discussion in their booth and were going from their table over to the bar to use the phone and back to their table. Then suddenly the woman yells “YOU BROUGHT A HOOKER INTO MY MOTHER’s HOUSE YOU COCKSUCKER” and storms out.

Restaurant is dead silent, and me and the bar tender just look at each other and burst out laughing and the guy shuffles back to his table.

11. The Showoff

This guy and this woman were on what appeared to be a first date since they were a little awkward with one another. Well, she was awkward. He was a ball of confidence. And bullshit.

I work at a seafood restaurant, and while I was going over the menu items, he would butt in with ‘facts’ about the meals. He said the Mahi Mahi was a type of dolphin. I said “oh, no, it’s called dolphin fish sometimes, but I assure you, it’s fish!” He said I was wrong and proceeded to tell his poor date it was actual dolphin and he has really fresh cuts of them at his place. Then when looking at our selection of crabs, he mentions he has 10 bags of King Crab legs at his home as well. The entire time he looked in his menu, he either knew everything there was to know about seafood or that he already had ‘fresher, better’ versions at his place.

I thought “seriously? Just go home then.” The lady wasn’t buying any of it and looked like she was going to laugh every time he opened his mouth.

12.They Said I Looked Like Their Daughter

I served a married couple not too long ago. The wife got up to use the restroom twice during the meal. Each time she left, the husband tried to get me to meet him for a drink. He was dead serious. The worst part was when his wife said that I looked exactly like his daughter who was away in college. I threw up a bit in my mouth after that comment.

13. Awkward

Not so much a date as it was a celebration. I work at a popular seafood restaurant. I walked up to an 8 top and ask what brought them out this evening, and one guest says “it’s my father’s birthday.” I look around the table trying to pick out the father and can’t, so I say ” ah, so who’s the birthday boy?” I’m met with a pause and a response of “He’s no longer with us…” I backed away slowly to get bread and drinks.

14. She Flirted With The Waiter The Whole Time

I was only bussing tables at the time, but overheard an awkward situation for my coworker who was serving them.

It was definitely a couple. Definitely a date. And the woman is not into it. Not sure why cause the guy seemed nice enough, but whatever. She’s just not feeling it. She was, however enjoying her server, David. To be fair, Dave was gorgeous and sweet and funny and all the girls at work said he was sploosh worthy. This woman agreed. I’m cleaning the table right by them when Dave asked if they wanted dessert.

The woman reached over, took Dave’s wrist, and purred “If you’ll share it with me. You bite mine and I’ll bite yours.” Right in front of her date. Dave awkwardly laughed, I nearly lost my shit, and the poor date just sat there.

Later, I went to clean the table, I saw she left Dave her phone number. Laughing, I gave it to him. He threw it out.

15. She Sprinted Out Of There

I wasn’t waiting on this table, just sitting next to it. This guy kept saying all this forward stuff to his date, and she was just trying to hide her face in her menu. He would say things like “Once this date is over I am going to show you the nasty!” Poor girl. Anyways she eventually just got up and left while he was in the bathroom. I could have sworn she sprinted out of that Japanese steakhouse, you could hear her breaths of relief as she made it out of the doorway.

16. “Call Me Daddy”

Working at a big chain restaurant I’ve encountered several of these but the one that sticks out the most is one where there was this old overweight man and a younger woman probably half the mans age. Right from the get go the woman orders a Long Island and I could tell something was up with these two but didn’t really think much of it at the time. It was when she proceeded to order not one but two more long islands (at this point I was regretting getting her that last one). They finished their meals, she was pretty intoxicated but not belligerent. I bring menus for dessert and as I’m presenting them the woman asks if they can order dessert to which the old man replies, “only if you call me daddy,” as I’m standing there. He then gives her the I’m gonna fuck you eyes she starts this half hearted giggle and I decided that I stayed at the table probably 2 minutes too long and told them I’d be back. They ordered dessert so I’m assuming she called him daddy.

Fast forward about two weeks later the old man shows up with some other girl half his age so I’m assuming he has a lot of daughters he likes to take out to eat, or you know, hookers.

17. Paid For Her Silence

We have a guy that comes in with a hooker (always a very young looking Asian girl) every other Wednesday for lunch and then his wife and him come in Friday night. He is always in my section and tips me very well for my silence.

18. The “Fucking Disgrace”

Used to wait/tend bar at a chain restaurant where after a few weeks you would get to know the regulars. This is in the UK so tipping wasn’t terribly high but there was an elderly couple that would come in every Tuesday and Friday for fish and chips with a few pints and a gin and tonic. After they arrive and order their usual, a couple seat themselves at the table next to theirs and begin their small talk. They were both twenty somethings and from their mannerisms it was clear that it was still early days for them. The guy is talking just a little too loudly and the conversation was all about him. “Oh yeah I used to make loads of money playing poker at casinos, I made so much that I’m now barred from all the ones in town. “I can totally bench press like 300lbs.” Basically the guy kept bragging about about shit the entire time and wouldn’t shut up.

The main thing he kept talking about was how much he could drink, since the girl ordered a beer as well and he latched onto it talking about how he could outdrink all his mates and he fucking LOVED beer. The elderly guy at the table next to his kept rolling his eyes at me every time I passed by, when I took their plates away his wife whispered “This is torture!” Eventually the guy has started to get quite drunk from trying to drink pint after pint in the space of an hour or so. When I come over to clear their plates and ask if they want anything else the girl begins to ask for the bill before he cuts her of asking for another pint. She quietly reminds him that he’s had five or so already and he tries to jokingly reply with “Bitch I can drink as much as I want.” Without a word the girl immediately storms off leaving the guy looking shocked as hell. The elderly couple leave their money on the table but before they leave the man turns to the dumbfounded braggart and just says “Son, you’re a fucking disgrace.

19. The Honeymooners

I used to wait at a country house hotel. It was pretty fancy, silver service, all of us in dickie bows and waistcoats so we tended to get the “upper crust” of society. This really friendly couple came in, very much in love and my boss whispers to me to be extra nice as they had just gotten married that day.

It was just themselves, no wedding party, bit strange, but they seemed very happy so whatever. I served their 4 courses and left them to it.

As I was collecting their deserts however I noticed a, chillness in the air. The next time I walked through the area, the woman was gone, the man just sitting there downing the wine.

The next morning, the man came downstairs, alone, and ate his meal, staring out the window. What was meant to be a week stay (their honeymoon) turned into me bringing their bags down to the car that day. They both sat in and drove off. I’ll never forget the….quietness. They both tipped and thanked me though, which was nice

Bit more information, they were both in their late 30’s early 40’s. And the night porter heard them arguingloudly.

20. “I Don’t Like To Share”

I was a waitress at a Japanese restaurant and this young high school couple comes in. The boy had been there many times before he and his family were fairly regular at the place. It was pretty obvious that it was her first time to our establishment/sushi Japanese cuisine restaurant. He I think was trying to be smooth and said he would handle the ordering. He gets a tempura appetizer and he has her try the first bite and we were in the Southwest area of the country and I overheard the girl say something about the wasabi looking like guacamole. He told her to have some of that to cleanse the pallet. Didn’t tell her that only a very small amount was necessary and she got a tempura sweet potato slice and dipped it like you would a tortilla chip into guacamole. I’m kind of waiting for him to say something that she doesn’t want/need that much. He doesn’t.

She bites into it and nearly turns fire truck red in the face from the burn. She drains her water trying to cool down her mouth, and runs out of that and reaches for his glass and he says he doesn’t like sharing things and that he will try and get my attention for more water. I bring her a small glass of milk and water. All the while he is checking his facebook/texts while his date is feeling like someone just lit a match in her throat.

21. “Never Ever Get Married”

When I was in college I waited tables in at restaurant that mainly serves chicken wings. A family of four walks in and the husband looks like a beaten man. Eyes down and slumped shoulders. The wife and kids order. When it’s his turn he asks his wife’s permission before ordering everything. “Can I have a Coke? Can I have 15 wings?” I kinda laugh thinking they are joking. Finally after ordering he finally looks up and asks me if I was married. I replied that I wasn’t and kinda laugh again thinking the he’s going to make a joke. The man looked at me with his dead eyes and monotone vice and said, “Never ever get married.”

I looked at him for a second expecting some sort of laugh or reaction from him out his family, but didn’t get a reaction from the wife. I got up and out their order in and watched the sad man eat his meal with no any interaction with his family.

22. The Cheapest CoupleTo Ever Live

An Indian couple, not sure what date it was, but the man brought two twenty dollar off vouchers that were one per table, to get around this the two sat at separate tables.

They also kept their bill under twenty dollars and he was on his phone the entire time even though that were sat next to each other at separate but close tables.

23. This Is So Sad

Sad date.

Couple’s anniversary and the guy wouldn’t keep up any conversation with his girlfriend. He was glued onto his phone the entire time.

I watched her mood go from excited (I guess she thought he had a gift for her, since she had for him), to this sad girl picking at her food with her fork for the rest of the date.”

24. The Magician

Not sure you can count this as a date but here it goes.

It was a woman in her upper 20s and an older guy in his 50s. I never really saw the two talk and all the conversation was revolving around myself although I never started a conversation with them.

Each time I came to the table the woman asked me what the most alcoholic drink was (cocktail the first time, martini the second, and beer the third) and subsequently ordered what I told her. She was obviously using this dude for a good meal and needed to get VERY liquored up.

Meanwhile the man was just awkwardly sitting there, sipping on his one whiskey drink the whole time either oblivious to what the woman was doing or just welcoming the idea so he could get lucky?

Here’s the kicker – he started performing magic tricks at the table sometime towards the end of the meal and when the woman went to go to the bathroom he gave me a playing card and told me to say that I found it in the book somehow.

I obliged because he said it would merit me a solid tip, but when I acted out my part she didn’t believe me and called him a liar.

Yeah that was awkward.

25. Ok, This One Is Also Just Super Sad

Had a young gay couple come into the restaurant I worked at about 10 years ago. They were adorable, but about 5 minutes in I think they recognized someone else in the restaurant and the date suddenly became not a date. I guess they were both still in the closet at the time. The rest of their dinner was insanely awkward, never making eye contact and they barely spoke the entire time. Felt really bad for them.

26. Not A Great Way To Remind Someone Who You Are

I waited on a man and a woman who got into an argument at the table, after which the man got up and left the restaurant. He stuck her with the check and apparently he had driven the two of them to the restaurant, as she was waiting outside the restaurant when I left work, waiting on a ride to come.

Jump ahead a couple of weeks, I walk up to greet a table where a man and woman are sitting. I welcome them to the restaurant and ask for their drink order. When I turn to the man, he excitedly says “You were my waitress last time I was here! Do you remember me? I was with the girl and I left her behind?” He was with a new girl this time though…poor girl probably should have left him at this point

27. WTH?! How?

I was waiting a table for two teenagers who where probably around 16 or so and clearly on one of their first dates. Everything appeared to be going well until the boy got his head wedged in the back of the chair. Fire brigade were called and after 20 embarrassing minutes he was cut free. Girl went to the bathroom and never returned.

28. The“Bitch” Who Liked Assholes

I’ve commented this in a previous post before, but it’s a good story so here it is.

I worked in a bar while I was in college and I had a guy come in before his date and told me that when ever he ordered a scotch what he really wanted was chardonnay. I must have given him an off look because then he got embarrassed and confided in me that he was really in love with the woman meeting him there for the date. He told me how she usually dated guys that were more macho and he didn’t want to order wine in front of her, but if he ordered anything else he would make a face because he didn’t like the taste. I felt pretty bad for the guy so I agreed. He seemed like a genuinely nice man and I wanted to help him out. Well the woman this nice man was in love with was a total bitch.

She came in with two other women to their date, he mumbled something to me about maybe not being clear, and plastered a smile on his face. The woman was extremely charismatic she was one of those life of the party women and the guy was very quiet… Anyways later in the evening he ordered another “scotch”, he had been doing this all night, only this time when I brought it to the table she insisted she wanted to try it. She said that she had never ha scotch before etc etc. It was like watching a train wreck, he tried to stop her saying things like “here let me buy you a glass” etc. well she took one sip and knew it was wine… I tried to help him going over and apologizing pretending it was my mistake, but she guessed the truth and started teasing him. Her friends joined in laughing as well… I felt awful and I could tell he was really embarrassed, even though he was laughing along etc. After a while he asked for the bill, I brought him the tab with his and the woman’s portion and he told me he was paying for everyone.

I felt so awful, the woman and her friends had all had so many drinks the tap was over 100 dollars, but I brought it and he tipped me 50 making me feel if possible more awful. They were my last table so I closed out with my manager and went back into the bar to have a drink with another girl that worked there. The group was still there so I decided to go over and ask to buy him a drink. I just wanted to I don’t know help him or something. Make him look good and possibly make that woman jealous. Well I went over there and asked if I could buy him a drink. He smiled at me, got up from his chair, and took me aside. He told me I was very beautiful, but I was too young to be hitting on men old enough to be my father.

I almost explained to him that I was just trying to help him, but decided not to. I figured that he could use the ego boost after that date”.

29. A Bad Break Up

Did not wait the table, but I had to clean up the mess. A young couple were having dinner when all of a sudden the guy stood up, picked up his plate of wings and threw the plate at the women’s face and stormed out the restaurant. Turns out she had brought him to dinner to break things off and he did not like that.

30. Holy Crap

I once waited on the engagement party of a girl I slept with a week before. I said congratulations.

31. Ditched

I don’t know if this counts as the “worst” date, but I definitely helped a couple not too long ago that definitely took the cake for the most awkward table. They both came in about an hour before close. The first thing the guy does is order a bunch of shots and a drink for his girl. Soon after he orders food for both himself and her. The next time I walked past them, I noticed that he’d moved his chair around to her side and was whispering sweet nothings into her ear. Keep in mind that I was the last server on and the restaurant was pretty dead so it was hard to miss. He kept this up for a while, even when I brought them their food I wasn’t acknowledged.

They’d barely eaten anything when I noticed that they’d suddenly disappeared, but they’d left some belongings at the table, so I knew they didn’t run out on the tab. I immediately assumed that they were in the bathroom boning at this point, so I informed a few of my co-workers that were working on their side-work. One of my fellow servers got ballsy and decided to go to the bathrooms and investigate for herself and found them in the hallway by the bathroom. She said from the looks of it, it seemed as if there was a debate whether or not to actually go into the bathroom. Soon after the guy ended up coming back to the table and asked me for the tab.

Then the guy disappears and the girl is left with the tab. I asked her if I needed to run her card, she seemed really upset, and told me that the guy was going to get a card out of his car. She waited for at least 10 minutes when I heard someone ask for me at the host stand. The guy wanted to pay for the tab but didn’t want the girl knowing he was back. Then he just left. It was so bad and so awkward.

My assumptions are this… guy wanted to get it on the bathroom, girl didn’t, guy bails on tab afterwards, comes back to pay it, then ends up ditching the girl.

32. The Overprotective Father

I use to work at an Italian restaurant on the not-so-great part of my town so the clientele there was always… interesting. But I will never forget when this younger couple came in on a date, that was chaperoned by the girls dad. Yeah totally understandable, maybe even kinda cute if they were pre teens, but no. These two looked like they were soon to be adults, definitely old enough to be on a big kid date. The dad sat himself at this smaller table RIGHT ACROSS THE WALKWAY from the two of them and seriously just stared. Didn’t order anything. Not even a drink. Just watched. It was so cringy seeing the reaction on the guy’s face when he realized what was going on, and how breezy the girl was being. She ignored the elephant in the room but the entire time he had this “could you fucking not?” look on his face. Uggh.

33. Typical Blind Date

Long story short – blind date. Lady was normal woman. Dude got naked in the unisex open concept bathroom during date. Twice.

34. The Things You Hear

My fiance is a waiter. He was serving a couple one time, and he started to approach them later to ask them how their food was, and right when he walked up, he heard the guy saying “And that’s why I’m breaking up with you” and the girl started crying. He backed off a bit to let that diffuse heh.

35. The Bird Savior

I was working a shift out on the outdoor patio of this restaurant located in a harbor right along the water. Happy hour just started and the place is packed, and I’m also training a new server. We are alternating tables when a strange older man sits down in our section with a youngish woman. My trainee takes them, and I hear a play by play of all the weird stuff he is doing: trying to order her drinks and food when she had just met him, and insisting on ordering the most expensive items. All of sudden, he looks out at the first boat docked near the restaurant, directly next to the whole patio. He notices the fake bird tied to the top of the boat flapping in the wind, to scare away other birds that are alive I’m guessing, and immediately decides to run to its rescue. He frantically asks us for a knife and instead grabs a steak knife from the food window.

At that point there are probably over a 100 people on the patio eating, and more inside, who can all see the boat, the not bird and the man. He runs out the exit, around the boardwalk along the patio, then down the docks. He proceeds to break into this boat, climb up to the top, and instantly realizes what he’s done. His walk back was so embarrassing I made my trainee serve them the rest of their meal. His date was obviously traumatized, and everyone in the restaurant had a good laugh.

36. There Was Blood Everywhere

I used to wait tables at the nicest restaurant in not just the town but the whole the area where I lived. Always rated #1 in the state, full of rich people and all that jazz. A couple sits down to order and I come over almost immediately to ask their water preference. The woman goes to scootch her chair in and, within what was probably a 10th of a second but I remember it as if it was slow mo, when she brings her hand back up I notice a spatter of blood go across the table cloth. Her date notices blood. He yells “YOUR FINGER!”. The woman looks down. I look down. Her finger tip, ring finger on her right hand, is gone. Blood is slowly dripping out of the stub and going all over the table. I stand there in shock going “uhh uhh uhhhhhh”. They both stand up and the man tips back her chair. The finger tip tumbles to the floor. He then picks it up and I run to get ice and tell the bartender to ask if anyone is a doctor (there were many) and to get the owner.

Turns out the front corner of the wooden seat had become disconnected from the hollow metal leg. Chopped it clean off. I swear to God to this day I can never scootch in a chair without thinking about it.

37. “Changed My Perspective”

One night I watched a couple order a pizza and a couple drinks and just eat in silence. they were in their fifties and seemed like they were probably married. I said to my coworker, “man, I hope i never end up in a marriage where I just sit across the table from them at a restaurant with nothing to say.” My coworker said, “actually, that’s the kind of marriage I want to have. one where you don’t have to impress each other or make small talk. Just exist peacefully together.”

Changed my perspective.

38.*Cringe*, Another Proposal

I had man come in for dinner (I work in a four star restaurant) sweating bullets from the time he sat down. He and the lady were obviously a couple and the entire staff guessed what would happen, especially after he ordered a $300.00 bottle of champagne to start the meal. She looked happy, but worried through the entire meal. When the dessert came he got down on one knee and I heard her say, “Please don’t.” Those two words stopped MY heart, I cannot imagine what this poor dude was going through. They had a hushed conversation and she ran out, literally ran, while he sat there still holding an open ring box. He finished the bottle of wine they had ordered during dinner, and pretty wasted turned to me and asked, “Why won’t she let me love her?” Just like that. Like I am going to give him some kind of answer to explain the complex and painful thing that has just happened. I told him that sometimes we fall in love with the wrong people, and the only people worth anyone’s time are the ones who give back what they get. He finished the bottle, paid his tab and walked slowly to the parking garage. I never saw him again.

39. The Freaky Couple

I was probably about 24 waiting in a 4 star restaurant in Cary, NC when a young couple comes in and is seated in my section. As I wait on them the female is quite obviously making moves on me and flirting like there is no tomorrow in front of this guy. I am friendly and joking but never let on that I think she is really really hot. They try to make it clear that they are just friends so I turn on the charm a bit. That is when the guy asks where the bathroom was. I point and give directions but he wants to be shown. After we are about 20 paces from the table he informs me that they both would like for me to come home with them.

Uh, twice the amount of people I wanted to have sex with from this table and politely decline. He goes to the bathroom and when I come back from the kitchen they were gone. $100 tip was on the table and it was an interesting experience over all, just not my cup of tea. She was mega hot, a real bombshell.

40. The Slutty Army Wife

Bartender at a dive bar for a bit and this was the worst thing I saw. Not really a “date” but close enough.

This lady, about 30 or so, would come in every so often and meet men. They’d get drunk and then leave together. Turns out she was new to town so all the local men were interested in her. After about 9 months of this she comes in with a bunch of girlfriends. I’d only seen one of them before so I’m surprised they would come to this bar for a girl’s night out or whatever. We had a small party room in the back and they had claimed it for the night. After about an hour of casually drinking a group of people come in, a few older men and women, a few younger people I assumed were not 21, and finally a man in a military uniform. The man asks around for the woman and a friend of hers says she’s in the bathroom. He asks me where the men’s room is and I see the main bathroom was occupied so I pointed him down the hallway to the bathroom most people don’t use because it’s kind of hidden behind the party room. He thanks me and proceeds to the men’s room.

Next thing I see is the woman running out of the bar and the military man bawling his eyes out to an older guy who I assumed was his dad. After the longest 5 minutes of my life they all leave, a friend says she’ll come back for the tab later that night.

About two hours later one of the female friends comes back in to pay their tab and she tells me the friend didn’t know her husband was coming back from Afghanistan and they wanted to surprise her. Since she’d been going to my bar a lot they thought it would be a great place to surprise her. Turns out she had been having sex with all the regulars in the hallway bathroom for months and never told anyone she was married.

41.Her Reaction Was On Point

Not a waiter but am a foodrunner in a restaurant. We’ve had some bad ones, but there was one that came in about a month ago that was fucking awful.

So, the guy is cool enough. I drop off their appetizer and he automatically asks what I suggest, then starts a conversation about video games. They’re super nice, to the point where I go to our manager and tell him, because as a small restaurant we often do nice things for guests to grow our list of regulars. I had suggested the salmon, and they both ordered the salmon.

Now, the restaurant I work in is a top class sushi joint, and fish is shipped in fresh, always on ice, from Loch Duart, perfectly fine every single time. I don’t think there has ever been a single case of food poisoning, which is pretty nice for a sushi restaurant with several years under its belt. Well, apparently eating the salmon destroyed this dude’s stomach, demanded it for free, was furious that his girlfriend was now going to be up all night with stomach pains from eating it. You may have noticed that the girlfriend hasn’t said anything yet.

Strange move, but our manager sends out freshly cut salmon sashimi (just the raw fish and nothing else) to prove it’s fine. Of course, he eats it and says its worse than before. He leaves to smoke, but the girl stays behind.

Turns out, it’s their first date. Girl is super pissed he left to smoke in the middle of their first date, asks her server almost in tears if that’s a normal thing. She apologizes for his behavior and says she just wants to get out as soon as possible before something happens and to please bring dessert and the check.

He comes back, we drop the dessert and check on the table, and while walking away I hear him pissed that she wants to leave. I don’t hear the rest of the convo, but I do watch and listen as she stands up, screams YOU’RE A FUCKING ASSHOLE, BRIAN!”, knocks everything (EVERYTHING) off the table and storms off. FuckingassholeBrian pays the bill, tips like 7%, and leaves. There was only one other table in the restaurant at this time, it being almost an hour after close, and the only one laughing louder than us was them.

42. Oops!

The dinner went normally. Just a man and a woman having dinner, obviously affectionate and on a date. As I am putting another table’s order in at the computer, the man races over to me and says, “I need to pay RIGHT NOW. I am on a date, and my wife just walked in.”

43. Completely Clueless

This guy with a reputation for not tipping brought his date in to my restaurant. He hit on me in front of her the entire night, she was clearly not happy with him. He wrote a zero in the tip line then on the back of the receipt left a phone number with a note… “Hey cutie 😉 call/text me sometime.”

Then there is the guy whosedate got so wasted she fell asleep at the bar and he left her there.

44. Manager Is A Saint

Was not my table, but I saw a guy get declined when he proposed… Manager comped his entire ticket, and his date left without him… It was sad and awkward.

45.The Champagne Volcano

I used to work at a Cheesecake Bistro in Richmond, VA. One of my first days on the floor, an african american couple came in and sat in my section. The first date vibe was palpable, as he was so overly-gentlemanly and “smooth”. His blind confidence hit the fan when she asked for Mimosa (champagne and OJ), and he stopped her and ordered “a bottle of good champagne, 2 flutes (champagne glasses, but NOBODY says that), and a glass of orange juice.

I started to open the champagne, but after the foil was off, he said “allow me”, and gave her a funny grin that was supposed to seem confident but was so over acted it lost that effect. I stood back ready to assist, but he managed to pop the cork and it landed in the booth behind her after arcing up in the air, and after the poor woman he was with cringing and flailing in fear of being hit. I just smiled and said “Bravo!” to lighten the mood and help him out, then left the rest of the items (glasses and OJ), and went back to get their salads.

Oh my way back from the kitchen, I heard the sound of water pouring, and nearly everyone in the restaurant was rubber-necking … in the direction of my table. This is when I realized I had made a terrible assumption when I figured he was going to pour the OJ into the champagne glasses and then pour the champagne…

As I came around the corner, what I saw was absolute horror on both of their faces, and on the table between them, a champagne and orange juice volcano shooting out of the bottle. This was epic. Science fair kids, eat your hearts out.

The date went on ok, and they both managed to avoid getting anything more than a splash on them. They seemed to be happy when they left, but my god, a $300 champagne volcano. That was priceless.

46. The Instagram Addict

So, I worked at this Mexican restaurant a while back and one afternoon there were these two teenagers that showed up for what I presumed was a date. The thing is, this was obviously not the best of relationships.

I show up to the table with chips and salsa to get drink orders. The dude is on his phone, hardly acknowledging me. The girl looks up and smiles since my introduction was probably the first human interaction she had since she sat down. I mean, honestly, on a date, talk to your date. I don’t care if it’s awkward, just do it.

I go, get the drinks and show back up. The guy is still on his phone and girl is still not on hers, still far too excited to be seeing this random ass waiter show up at her table. I give the drinks, confirm that they don’t want an appetizer, and go to the back so they can have some time to choose what they want to order.

I instantly get asked from multiple other servers what’s going on at my table. I don’t think restaurant patrons understand, but waiters do talk. Not everything is mean, no food is spat in, but people talk. I respond with I don’t know why they aren’t talking and receive multiple “poor girl” and “he should get his ass off his phone” from waitresses and sassy-gay-friend waiters alike. I agree with them all.

Fast forward through the awkward ordering phase to when their plates of tacos and nachos are almost finished I’m asking them if they want any dessert.

As the word dessert comes out of my mouth, the girl looks at me and I swear her eyes tell me that I had better bring the tab so she can leave. I don’t even push the option and quickly pull the check out of my pocket, setting it on the table. Then, in a stroke of luck, the guy sets his phone down for the first time. I still don’t know how Instagram is that popular-I get bored on it after five minutes but this tool ignores his definitively attractive date to peruse random ass accounts.

I check them out, get some plates out of their way, and they leave. The phone usage is, as Liz Lemon dubs it, a definitive “deal-breaker.”

47. What Part Of The Cow Are Pork Chops From?

I worked right down the street from a private college full of kids who’s parents have always done everything for them. I had a couple come in, it was obviously a first date, she was obviously from the college and he obviously wasn’t. We had a lunch special on a plate of pork chops with three sides for ten dollars she looks at me and ask if we got the cows from Mississippi or Alabama. I’m expecting this to be a joke because even though the parents usually pay the kids way into the college the expectations are very high. I look at her date and he has the omg did she really face on. She was dead serious so I said I’ll go check. When I come back I go to say btw pork is pig not cow and she interrupts me to order. So I take both orders and put them in.

When I bring out the food the guy ask for hot sauce and when I told him we had Louisiana hot sauce or the other brand he said “now does the hot sauce come from Louisiana or Mississippi “… He cracked this type of joke with me the whole date and it all went over her head… When she finished I asked if her pork chop tasted like it was from Ms or Al she said for sure Ms it was awful and dry. The guy leans in and says it was probably awful because pork is pig and it’s probably dry because you wiped every bite with your napkin.

48. So Dark Not Even Light Can Escape It

I’m a bartender at a major chain restaurant. A couple stumbles in about 15 minutes before close. They’re talking loudly and sit at the bar. I’m a little pissed off so I finish wiping down the bottles before acknowledging them. I can hear everything they’re saying but it’s all very coded language so I have no clue what they’re fighting about.

“You promised me three times!”
“I can’t I can’t, I just can’t do it,” the woman says.

When I turn around and ask them what they would like to drink the man orders 10 shots of the strongest liqueur we have (which is Rumplemintz). I tell him I can’t serve that many shots to just two people.

He says, “There’s three of us. I’m trying to make it two people,” and pulls out a $100.00 bill and lays it on the bar.

Read more: http://thoughtcatalog.com/eric-redding/2016/01/waiters-share-the-most-train-wreck-cringeworthy-dates-theyve-ever-witnessed/


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