Waiters Share The Cringiest Dates They’ve Ever Served
Employees in the service industry are well aware that there’s never a dull moment in their line of work. While to outsiders it may seem like a terrible gig, it can often be quite the opposite. Of course, few people would call it their “dream job,” but half of the fun is in the funny and bizarre interactions with customers. There’s just so much awkwardness to be witnessed as a waiter or waitress.
Some of the most cringeworthy interactions come from serving people who are on a date. Read on for some examples of these stories.
Don’t forget to check the comment section below the article for more interesting stories!
#1 Blatant Disrespect
A girl hit on me in front of her boyfriend while I was serving them. The boyfriend walked off after staring her down and the girl just awkwardly sat there alone for a while. I asked someone else to take over her table because it was too awkward.
#2 Brutally Honest
It was their first date. I would say they were both in college. As they were eating, 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. I said yes, so I actually have to go.”
#3 Learning On The Job
I had a couple come in one night and everything seemed to be going fine. We just hired a new server who I had to train. I asked her if she had any questions. She was still nervous about greeting tables, so I told her she could just shadow me and watch. We went over to the couple’s table and out of nowhere, the new server screamed: “YOU TRAMP! I KNEW YOU WERE CHEATING ON ME!”
Turns out, the guy was her boyfriend and he was on a date with his side chick. He didn’t know she just got a job there. She didn’t get fired for what she said.
#4 Thank You, Next
A guy came into the bar on a weeknight— he was an average-looking guy, probably in his late twenties. He sat down and asked for a drink. He was nervous because it was his first date in three years. 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.
The woman walked in, went up to the guy and I’m thinking wow, she actually came. She looked at him and asked, “Are you Joe?” The guy replied yes, and got up to properly greet her, looking incredibly excited… Then, she said, “No thanks…” and just left.
What a foul creature. Joe and I proceeded to get way too tipsy for a Tuesday. Poor average Joe.
#5 Pizza Face
The husband and wife fought. The wife cried. The husband got up and threw a pizza slice at her face.
#6 A Pitiful Proposal
I worked at a fondue place. It’s usually a two-hour meal for two people. Four courses, the works.
A couple came in and he had prearranged with us to present an engagement ring with the chocolate course with melted chocolate on the plate saying: “Will you marry me?”
Apparently, the entire meal she was explaining to him how bad he was at being in a relationship. He was too needy, too emotional, and somehow also didn’t spend enough time with her. It was an hour-long breakup speech.
We came around the corner with candles lit and the engagement ring on the plate. The table next to them did everything they could to wave us off. I was holding a camera to capture the magical moment… which never came. He tried to get his prepared remarks out, but it was so bad we eventually left the dessert at the table and tried to act like nothing had happened. She left before the check came.
#7 Falling For Her
The date seemed to be going well, but the guy was nervous and fidgety. He would rock back on his chair a little bit as he talked and eventually flew too close to the sun. He toppled his chair backward and knocked himself out cold. He also went #1 in his pants.
He had to be taken out of the dining room on a stretcher while his Tinder date did the honorable thing and immediately went to the bar to order shots.
We gave them to her on the house.
#8 Divorced Over Drinks
I was working at a wine bar when a married couple sat down. It was 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.
#9 The Signs Were There
I served a deaf couple that was having a fight. They were both signing furiously. At some point, the woman started crying and signalled to me for a stack of napkins. She whipped out a pen and started writing paragraph after paragraph angrily. It was awkward because I kept having to come back to the table since they ordered multiple courses. When they finally left, they tipped me pretty well, so I guess it wasn’t too bad?
#10 Making Him Mad
There was a couple at my work having drinks. The girl went to the toilet, came back, and admitted that she’d been sleeping with the guy’s brother. Apparently, glasses were thrown across the room and they both got kicked out.
#11 Overindulgent Order
A really little guy—maybe 5’4″ and 120 pounds—comes into the restaurant with a gigantic woman—probably 6’1″ and easily 300 pounds. Both are tatted up with piercings to match.
The woman orders her dish and before I get the guy’s order, he says in a sexy voice, “I think you want more than that.” She smirks at him, saying, “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 small role in this bizarre couple’s eating fetish for like, three years.
#12 Playing For Keeps
A girl brought two Tinder dates with her and played them off each other, game show style. They seemed to be unaware this was what would happen. Splitting the bill was hilarious.
#13 Perfect Match
This wasn’t so much as awkward as it was slightly unusual. I served a young couple at a high-end Italian restaurant and they came in wearing matching outfits. I asked them what the occasion was. They were celebrating their two month anniversary. I’m so glad they found each other.
#14 Tortured By Talk
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 kind of sideways, playing on her phone. The body language shift occurred during the hour. He didn’t stop talking the entire time.
She did give some nods in response; even perked up a few times to contribute. But his monologue never stopped.
#15 Back Door Breakaway
There was a couple sitting at the bar together. It seemed like it was their first date. Maybe after 30 minutes of them being together, the dude comes running to the back where I was rolling silverware 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.
#16 Riled Up Regulars
I witnessed 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 got up and started walking across the restaurant to leave. The woman stood up after him and screamed across a crowded restaurant, “AND YOU MADE ME TOUCH YOUR BUTT!”
I never saw them in the restaurant again after that night.
#17 Dessert, Diamond, And Desperation
I worked at a high-end resort waiting tables in the fine dining restaurant on-site. 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.
I brought out the ring, and the girl he was with says, “Damn it, I’ve told you before I’m not marrying you.” He flips out, while she’s super calm about it and basically treats him like a child having a tantrum. He left and she ate the dessert.
Eventually, he came back, paid, and they left together. Super awkward.
#18 InEXcusable Behavior
I waited on a middle-aged couple who seemed perfectly nice. The man asked me where he could go to get some air. 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, and what I was doing later. Thankfully, I was able to excuse myself to the kitchen. Serving that table was awkward after that, especially since she kept touching and complimenting him.
#19 Unhappy Meal
Not technically a waiter, but I worked at McDonalds (one of the less trashy ones) and a couple came in. The woman sat down and the man tried to order. He hesitated with what he wanted to buy. He eventually ordered two meals that we gave to him and he sat down. What followed was a 10-minute shouting match about how he wouldn’t take her on a “proper date” and how he messed up even a McDonald’s date. I guess he ordered the wrong thing.
#20 Hole In None
The couple started shouting, then they both went into the washroom. We thought they were smashing and dashing, but they came back. I heard some of their conversation and it was so awkward.
Guy: “So do you golf? Cause I golf.”
And it went on like that for their whole date.
#21 Afternoon Delight
I was a bartender. I served two strangers chatting with each other across the bar. They hit it off, talked a lot, and were clearly into each other. When they moved closer, I turned away to help other customers, not paying much notice. When I eventually turned back around, I realized that he was now standing behind her with his hands up the back of her shirt, giving her a sensual back rub while her eyes were closed. This was at lunchtime.
It went great for them, but was awkward for everyone else in the bar.
#22 A Social Experiment
I was a bartender at the time. They were right in front of the bar.
An attractive woman came in with a very loud dude who never took off his rollerblades. They were in the bar for about an hour before he thanked her and left.
He thought it was a date. Apparently, she was doing sociological research on people who use Tinder.
I was relieved.
#23 Entrees For The Girls
When I was in school, this old guy used to bring in a bunch of different young ladies. I thought they were his daughters until one day, I noticed lots of touching. A real life Hefner.
#24 No Game
I sat next to a table where a guy was explaining the plot of a new video game to a girl on their first date in incredible detail. He was not catching on to the signs that she didn’t care one bit. She would try to change the subject and he would come back to the video game. I can’t believe how nice she was about the whole deal. By the end, he said he had a great time and tried to set up another date. She was very clear, in a polite way, that she did not want another one, but he still didn’t catch on. She was incredibly attractive. I had so many questions.
#25 Check, Please
One of the waitresses at a restaurant where I used to work at told me this.
There was a couple, apparently on a first date. As she would come by with drinks and to take their order, etc., she noticed that they were hardly talking or looking at each other, if at all. The girl was clearly not into it. Finally, when they were finished with their meal, the waitress asked if the bill would be together or separate. The guy said “together” and the girl said “separate” practically at the same time. Seems like they each had a different experience on this date. It was very awkward to hear.
#26 Breakup And Bounce
The dude ordered so much food for them. I thought it was a little weird. He then asked me to give them some more time. After about 20 minutes, I looked over and saw that the girl hadn’t touched her plate at all, while the dude was almost done with everything on the table.
Next thing I know, the girl is crying and the dude is nowhere to be found. Turns out, that was their breakup dinner… The dude didn’t pay the tab, either. He left her with extra food and an $80 bill.
#27 Coming On Too Strong
I was working at a local Mexican restaurant. This guy came in saying he was going to be meeting someone for a date. She was coming a little later. He asked for a more private spot which wasn’t hard to do—it was like, 9 p.m. and we were almost empty. The server sat them at a small booth in the back room. He told her it was going to be a special date. It was a couple of weeks before Valentine’s Day and we had some candles, so she lit one for them and put it on their table. He had also brought in some roses and a vase for the table. He was showing her this necklace he had bought and was going to give to the woman.
The woman showed up and saw the whole set up. She looked super uncomfortable. This guy was trying to physically put the necklace on her and she refused to take it. It was apparently only their second date and this woman was freaked out.
She ended up leaving.
#28 Family Matters
I was running food to a table. As I started distributing the food, I said, “Ok, who has the chick—” and before I could finish all I heard was: “Well then maybe you shouldn’t have slept with my sister.” They both looked at me. Longest five seconds of my life. I just kindly set the plates down and allowed them to sort out who had what.
#29 Being A Little Shellfish
Last night, a couple came in. The woman was rude and annoying. At one point, she grabbed the dude’s lobster and he questioned her. She had her own lobster dish. She made a huge fuss and when he said, “Fine, here, you can have some,” she said, “I don’t want that, I would rather end myself!”
#30 Caught Cheating At The Cantina
An 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 with chips and salsa when she suddenly grabbed the man’s frozen marg and threw it in his face. She shouted, “If you’re gonna have lunch with your wife then you should stop texting me!”
Needless to say, I had their food boxed up to go.
#31 Proposing A Breakup
Not a waitress, but I was sitting close to this couple. The guy was on one knee and holding a small black box. When she opened the box, he ran away. There was a small paper inside. After reading it she started to cry. Turns out, he broke up with her. It was funny and sad at the same time.
#32 Smooth Sailing
I had a young couple come in for 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.
As I wipe 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 dead serious. He’s got a confused look on his face but eventually says, “Oh, yeah, I get that.”
#33 Lover’s Quarrel
This couple came in on Valentine’s Day. I recognized the woman from the gym. She basically yellec at him on the phone the whole time. Kinda crazy. Anyway.
We have little paper table tents that host puts on the table. One of them must have written a guest’s number down quick on it and not realized it. The woman sees the number and starts freaking out about it. We’re just watching this all unfold. The server took a drink and app order. She continues to berate him. Drinks come. She’s still yelling at him, calling him a cheater, tramp, all those expletives. Then, all of sudden, he just gets up and leaves. She is just staring off, dumbfounded. The server places the app down on the table. She stares off into space for a good five minutes and then she gets up and leaves. I hope that man she was with is still alive.
#34 Meal Exchange
A young high school couple once came in and got some burgers. They were sitting side by side and it seemed normal. Then when the food arrived they would take a bite of their food and while they were still chewing, they would make out. They did it multiple times. It was like they were mixing their burgers together in their mouths.
#35 Compensated With A Car
I had a husband and a wife come into a very high-end restaurant when I was 20. It was country club-level stuff for the wealthy. He told his wife at dinner that he was leaving her for another woman he met in Thailand. It was cold as ice. He said he would leave his apartment in NYC for her and his Porsche.
She cried. He got up and left.
#36 Caught And Confronted
I 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 seated 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 of 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.
#37 Friend-Zoned Real Quick
I saw a guy and a girl 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 an awkward silence.
It looked like everything was going well for them, I guess not.
#38 Love Tipsy
I saw this much older couple come in and you could tell they were already a little tipsy. It’s normal. Well, these guys weren’t even married. They were “friends” just hanging out… at least, 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 him home and leave her husband. She was 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.
#39 Cake Competition
They ordered a single desert: a slice of cake. I forgot to bring a second fork so I dropped the one fork I did bring in the middle of the table and joked that it’s a race and the loser pays the check. She reached for it first but his arm darted out so fast that he easily took it. He then started housing that slice of cake. There was just no time to get another fork to the girl in time. She just kind of blankly stared. Then he smiled victoriously.
#40 Declined Twice On Date
I work at a sports bar and two people who I went to high school sat down at one of my tables. The girl was one of the popular ones in high school and the guy was a jerk who played on one of the sports teams I was on. Everything seems to be going well for both of them until it came time for the check. The guy went to pay it with a card but it declines. He goes, “Oh, that’s weird,” then gives me a second card which also declines. The look of embarrassment on that guys face when the girl had to pick up the tab was priceless.
#41 A (Literal) Broken Heart
I work at a Red Lobster. One time, I was serving a table of two who had clearly met up for a first or second date. Both of them seemed very wealthy, but the gentlemen specifically seemed a little odd.
…Long story short, the gentlemen began coughing and went to the restroom for a second to get himself together. He ended up taking around 30 minutes. The lady requested we go in and look for him, so we did. Turns out, he had a massive heart attack and we found him lifeless on the bathroom floor. We didn’t quite know how to tell the lady, or even what to do really (besides call the police), but by the time we went to look for her she had taken all of his things and left. Just a weird, messed up scenario.
#42 Bartending Not Babysitting
The worst is when you are the only three people in the bar and the couple is fighting while trying to drag you into it. “Oh? Really? You’re going to have another drink? Really? Really? Excuse me can you cut him off?”
Nah. They’re not falling down or slurring and I’m sure you are recognizing signs of what is going to turn into a terrible night for you, but I need to make money.
#43 Public Indecency
I walk over to introduce myself and take their drink order. The girl is on her phone looking through nude pictures of herself. I notice for a second and look away. The guy is clearly not amused and slams the phone out of her hand. They were gone when I came back.
#44 Sharing His Stand Up
The most awkward couple date was when a guy waited for his online blind date for two hours. When she did not come, he made me take a picture of him sitting there alone to post on Facebook.
#45 Energy Suckers
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 also said not to fear them because they wouldn’t hurt anyone. They said they didn’t need our food for sustenance, they just 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 for the night. The waitress said okay and gave me a side glance over her shoulder that I knew meant, “I better get a good tip for this…”
The couple clasped each other’s hands, closed their eyes, and made sucking sounds for a solid minute before leaning back in their seats and sighing as if they had just had a turkey dinner. The waitress was indeed tipped well for her delicious energy.