March 20, 2023 | Eul Basa

"Check Please": These Waiters Witnessed Disastrous Dates, Fights, And Breakups

A restaurant is the go-to choice for many couples, which means that waiters have seen it all when it comes to romance. Lasting relationships, steamy one-offs, and...truly horrific attempts at "dates". From botched proposals to embarrassing revelations, these are the biggest disaster dates servers have ever witnessed.

1. No Big Deal

I was bartending at a restaurant in San Francisco, and this guy came in and ordered a martini. He downed it and then ordered another one. Halfway through his third, I finally understood the horrific situation. He called his wife, abruptly asked her for a divorce, and then hung up. He then started talking to me about baseball and how the Red Sox were doing.

Waiters Saw Disaster Dates factsShutterstock

2. Au Revoir, Shirt!

I used to work at an upscale fine dining restaurant in Vail, Colorado. I once saw a lady walk in off the street, throw a glass of red punch all over a guy’s white shirt, and then leave. The guy did not react at all. He just sat there and continued eating his spaghetti plate as if nothing had even happened. He could not have cared less. It was hilarious.

Waiters Saw Disaster Dates factsShutterstock

3. Off to a Great Start

I used to be a waiter for large corporate events and weddings, and I had a very typical bridezilla to deal with at a wedding one weekend. She ended up getting hammered at the reception and slept with a groomsman in the honeymoon suite in the middle of the wedding reception. Word soon spread throughout the venue about what had just happened. Needless to say, her new husband left her immediately.

Wedding Red Flags factsShutterstock

4. Not-So-Secret Admirer

I was a bartender at a country club. I once watched a woman curse her husband out at their table because her kept flirting with the waitress. She got really loud and made a huge scene. Eventually, she stormed out of the restaurant, with all the rich snobs watching. The waitress felt very guilty about it, but she told me that the guy had been coming in there often and tipping her 100% of the bill every time.

Waiters Saw Disaster Dates factsShutterstock

5. Right Place, Wrong Time

I worked briefly as a waiter at a semi-nice place near where I live. I once had a couple come in for a date who we had seen there a few times before. I think we were their regular dating spot. But today was different. The girl was clearly very sad, and was talking about how her uncle was really sick and was probably going to pass soon. That's when the guy made a huge mistake.

In the middle of this discussion, the guy decided to pull out a ring and pop the question as if nothing was wrong. Seriously, dude? Read the room!

Waiters Saw Disaster Dates factsShutterstock

6. Why Me?

Bartender here. A couple on a blind date once took their seats directly across from me. I then had to pretend I couldn't hear the guy awkwardly asking the girl what she saw in him, over and over again. He was well over 40, balding, overweight, and visibly intoxicated. She was about 30, very pretty, friendly, and level-headed.

He was aggressively shouting: "Listen. I see you over there, just amazing and gorgeous, and I'm wondering what you're seeing in me. What do you think?" She just smiled and cringed while making an active effort to sidestep his questions and change the subject at least three times. He continued ordering more drinks for the entire night, and his line of questioning never changed.

Worst Dates factsShutterstock

7. Political Theater

I work as a waitress at a nice little tapas bar in England. On the day the results of the last election were announced, we had a couple on a first date who had voted for opposite parties. The guy was pretty chill, but the woman came to the bar and whined about the results for 15 minutes straight. Then, she insisted that he pay. Suffice it to say there wasn’t a second date…

Worst Dates factsShutterstock

8. Tree Hugger

I work in a restaurant that’s near a pretty large university, and most of our customers are students. One time, a young guy came in with a as his date. He sat with it at the table, cuddled up to it, and ordered it food, drinks, and dessert. He was a total gentleman to the plant. Turns out, he had lost a bet with his frat brothers.

Waiters Saw Disaster Dates factsPixabay

9. Raising the Stakes

I used to be a waiter and bartender in a yard house. For those who don’t know, a yard house is essentially a corporate place that's a nicer sports bar with a ton of drinks on tap served in stupid, giant novelty glasses. I once had a couple at the bar during happy hour, drinking from one of the big glasses. They ordered some onion rings that were half price.

He jokingly proposed to her with an onion ring. She started laughing, and jokingly said yes. As soon as she said the word "yes," he busted out an actual ring from his pocket. She wasn't laughing anymore. Awkward!

Waiters Saw Disaster Dates factsShutterstock

10. A Saucy Way to React

I worked at a bar in a hotel for more than five years. I once had a couple come down from their hotel room and sit at one of my pub tables for dinner. From the moment they sat down, you could tell that the wife was furious about something. She was unbelievably pleasant towards me, but did not say a single word to the man at the table.

I got them their drinks and then took their orders. He ordered a steak and she ordered the sauciest pasta dish we had on the menu. About 20 minutes later, the wife still hadn’t said a word to the man since they had sat down. Their food was now ready and my food runner set it on the table for them. That’s when things got interesting...

Right as I was about to walk over to see if they needed anything else, I saw the woman stand up and shout “I hate you, John!” as loud as she possibly could. She then picked up the plate of pasta and dumped it all over his head and down onto his lap. She then very calmly walked out of the bar and back up to her hotel room.

I spent a few minutes helping the man clean up and got my manager to come handle the situation from there, as it was way above my pay grade at that point. Later in the night, the woman came back to the bar without the man and we talked for a while. Turns out, he had admitted to cheating on her right before their dinner reservation. I never saw either of them again.

Waiters Saw Disaster Dates factsShutterstock

11. Nothing Can Come Between Us, Except...

I worked at an upscale seafood restaurant for about a year. One particular woman would bring in a different date each week. Every single time she was there, she would start the date by erecting some kind of barrier on the table between herself and her guest. I’m talking salt and pepper shakers, menus, dishes, drinks, etc.

Whatever she could get her hands on at the table, she would use to construct this physical barrier with. She would then carry on with the date and with her conversation as if things were completely normal. The confusion and distress on the faces of the men she would bring in was always my favorite part of Saturday night. Still have no idea what was going on.

Awkward Crush factsShutterstock

12. Some Questions Are Better Left Unasked

I’m a waiter in a restaurant that a lot of people come to for dates. I once had a table where the couple seemed to be having a great time together. Throughout the evening, I watched them enjoy drinks, appetizers, the best entrees on the menu, a luscious chocolate mousse cake for dessert, and even a few rounds of champagne.

Then, at the end of the night, I went over to the table and asked if there was anything else I could do for them. The guy gave the worst response possible. He turned to me and asked, “What can I do to ensure that this pretty lady will let me sleep with her this evening?” The girl instantly turned beet red and her jaw dropped.

I was pretty shocked myself, and I said, “I think you were pretty much well on your way, until you said that!” The girl just nodded and said, “Yup".

Waiters Saw Disaster Dates factsShutterstock

13. Trust, But Don’t Verify!

I once witnessed a very awkward first date in a restaurant. In short, the girl stated that she was allergic to pineapple. The guy basically responded by implying that he didn’t believe her. Later in the evening, when she had left the table to take a phone call, he secretly scraped some pineapple glaze off of his dessert and onto her spoon.

She came back and started eating without noticing too much at first, but then quickly had a severe allergic reaction. The guy freaked out and tried to run away, but he got stopped by a customer from another table who was suspicious of him. The manager administered the girl’s EpiPen and called an ambulance, as well as the authorities. It was an absolute circus.

Waiters Saw Disaster Dates factsShutterstock

14. A Thousand Pictures Are Worth a Million Words

I used to be a waiter at a very famous, upscale restaurant. One evening, a gentleman approached the hostess requesting that someone take pictures of him proposing to his girlfriend. Since I was the closest staff member to the hostess at the time, I was tasked with performing this duty. Little did I realize what was about to go down...

After awkwardly stalking the table for a solid hour, the moment was inevitably approaching. I set myself up at an angle where she couldn’t see me. When he busted out the ring, I started taking as many pictures as I could. Anyone who has tried to capture a moment like that on camera knows that you’re not really watching what’s going on, you’re just trying to frame it.

After taking about 20 or 30 pictures, I slowly realized that she was declining the proposal. The scene before me was quickly degenerating into a full-scale dumpster fire. However, I was far enough away that I couldn’t hear what was actually being said and couldn’t be sure of what was transpiring. So, I continued taking pictures just in case.

Finally, I stepped back and watched as she stormed out of the restaurant in embarrassment and he scrambled to pay the bill and chase after her. He’d requested that I use my phone for the photos and then send the best pictures to him afterward. Needless to say, he never approached us for the pictures and I now have about 100+ pictures of a wedding proposal gone wrong.

Awkward Moments FactsShutterstock

15. Dining and Diving

I was once a bartender for a couple on a Tinder date. They talked for about an hour. Then, he went to the bathroom but left his jacket on the back of his chair, with his wallet and keys inside. Her reaction was chilling. She immediately grabbed them, ran out the door, took his car, and treated herself to a shopping spree.

When the poor guy came back and saw what had happened, he refused to report the incident for over an hour because he insisted that “everything was going so well!” I felt really bad for him.

Waiters Saw Disaster Dates factsShutterstock

16. Free of Charge

This couple once came into my bar. At first, it was business as usual. I took their orders and brought out their drinks and food, including dessert. Nothing seemed out of the ordinary at all. However, as the night went on, this couple began to argue very loudly. As they worked their way through their dessert, the girl was shouting at the top of her lungs. About what?

Well, about the fact that the guy didn't bring a battery pack to charge their phones. This girl was straight-up raging at this dude. Luckily, it was a really slow night and they were the only ones in the restaurant. I tried to defuse the situation by offering to charge their phones if they had a cable.  I felt for the guy, because I was that guy at one time. I shouldn't have.

This is the point where I feel like I should have suspected something was up. The guy hands me what looks like a cheap, busted up prepaid phone you get from the supermarket and what looked like a chewed-up charger cable. I ran to the back to go and charge it, only to find out the cable wasn't compatible with the phone. Then I discovered the truth.

I went back to them and found out that they had run off without paying as soon as I was out of the room. Honestly, I was more impressed than I was upset.

Waiters Saw Disaster Dates factsShutterstock

17. Picture Perfect

I used to be an ice cream shop employee, and I once had a couple come into the store on a date. They were about 16 years old and were being chaperoned by the girl's mother, who insisted on taking photos of them every few minutes. Not just candid photos, but posed ones. It took them nearly 20 minutes from the time they got their ice cream until the time they finally left, because the mom just wouldn’t stop.

The girl seemed pretty embarrassed by her mom's behavior, and the boy looked immensely uncomfortable with the whole situation.

Waiters Saw Disaster Dates factsShutterstock

18. The Silence Was Golden

I'm a waitress in my father's restaurant. It's not that big, but we're usually full during weekends. A lot of couples come here because it's kind of "chic" for a French restaurant. Anyway, once there was a couple in their early 30s. The dude arrived earlier than the girl, so I thought it was something like a date. Turns out, it was something else entirely.

The girl ordered everything. She chose all the dishes, the dessert, and even the drinks. All without even asking the guy what he would like to have. They both didn't talk at all during the meal. They only said “good evening". Pretty weird for a date. Then, when I came to their table to serve the drinks, they started to argue about their relationship right in front of me.

The dude was convinced that she had cheated on him. After a minute or so of arguing, she admitted that she did, and said very loudly that he was bad in bed. At this moment, every single cell in my body was cringing. They kept arguing for about ten more minutes until I finally decided to stop them. They were almost yelling and disturbing the other customers in the restaurant.

The woman then ordered an expensive bottle of wine, and then left the restaurant with the bottle. I felt so bad for the guy that I gave him a free soda.

Waiters Saw Disaster Dates factsShutterstock

19. Not the Time for a Magic Trick...

I once witnessed a woman ghost her date at the end of the night. It was a fancy jazz club, and the couple racked up what I assume was at least a $500 bill. They had ordered a ton of expensive drinks, and even a few expensive entrees. When it came time to pay, the woman snuck out while the man was in the bathroom, and then just disappeared.  The dude was totally distraught.

Waiters Saw Disaster Dates factsShutterstock

20. What Happens in Vegas Stays in Vegas

A guy and a girl were fondling each other at my bar one evening. Another guy then joined them, and they quickly separated and behaved themselves. The three of them went off into the casino together, but they all stopped back for drinks a few times over the course of the evening. As they got more drinks in them, I found out what was really going on.

In the middle of the night, the "friend" came in, did a shot, and walked away. I could tell he wasn't happy. He later comes back and says he has a couple of hours before his plane leaves. We get to chatting, and he tells me he just broke up with his girlfriend, as he suspected she snuck up to the room and slept with his best friend when he couldn't find either of them for an hour.

I ask him if the friend and girlfriend were the two canoodlers I saw. He confirms this, and I let him know he's making the right choice, since they were making out at the bar before he came down. He thanks me for confirming, leaves me a huge tip, and lets me know what's happening in case there is any confusion with the hotel.

An hour or so later, the canoodlers are back at the bar whispering and arguing. I casually ask if everything is okay. They say they are locked out of their room and can't find their friend who paid for it. They tried to charge their drink bill to the room, too. I told them that their friend had been in earlier, but checked out and his flight was already in the air. Then I watched the meltdown.

Since the scorned boyfriend had been bankrolling the whole thing, the cheaters now had no place to stay for the week and no money for even basic food. They did everything they could to get out of paying for their drinks, as they were very expensive. They left no tip, and didn't have a place to sleep or even change clothing at 5 AM. Serves them right.

Waiters Saw Disaster Dates factsShutterstock

21. You Know What Happens When You Assume!

I once had a couple that I didn't realize was a couple and, once they were done with their meal, I asked if they would like separate checks. I honestly thought the woman was the man's mother. They both looked at me with confused and offended expressions on their faces, and replied with "Um... One check please". They're now regulars who come in almost every week...and despise me.

Waiters Saw Disaster Dates factsShutterstock

22. Bagged Meal

I used to work as a hostess at a popular restaurant chain. One time, this guy makes a reservation at the most frequently booked table. It’s by the window, all romantic, etc. It’s also super visible from any other part of the restaurant. He comes in, all dressed up and with a suitcase. Strange, but okay. A few minutes later, his date arrives.

They laugh, flirt, and put on a whole scene. Based on the way it was going, we actually thought it was an anniversary dinner or that he was going to propose or something. Boy, were we wrong. Halfway through the evening, she starts screaming at him. He broke up with her in the middle of dinner. That's where the suitcase comes in.

The bag was full of all her things, which he had packed beforehand. He then paid and left her there sobbing at the table alone. We got her a brownie on the house, because we felt awful for her just watching that.

Waiters Saw Disaster Dates factsShutterstock

23. On Second Thought...

I was a waiter at a nice restaurant. I once had two young people coming in, obviously on a first date. The girl warned me right at the outset that she had a seafood allergy. Nevertheless, the guy ordered seafood almost immediately after she said that. It took him a couple of seconds to understand what I meant after I asked him if he was sure that it was a good idea.

He then reluctantly agreed and ordered some chicken. You know, you really should not kiss someone who just ate seafood if you have an allergy to it. I hope the rest of the date went well for them after that.

Waiters Saw Disaster Dates factsShutterstock

24. The Great Escape

When I was 22 years old, I worked as a busboy at a 200-seat restaurant that was part of a sporting club. I'd been there for long enough to have a feel for the personalities of the customers. On this one particular night, one of my tables was a first date. The girl was lovely, all smiles and very pleasant. The guy was sort of normal, but seemed a bit quiet.

When I was at the table, the guy gave off some fairly clear signals that he would prefer to be left alone. That's okay, some customers prefer minimal service. What I did notice, though, was that he was talking to the girl quietly, but forcefully, and almost non-stop. Sometimes, he was gripping her arm firmly, in a way that suggested that she wouldn't be able to pull away easily.

I couldn't hear a word that was said, but the lady was looking more and more terrified all the time. Like, nearly about to wet herself terrified. It was a complete change from her pleasant nature that she had displayed when they first walked in. I told the waitress on the adjacent section that I wasn't sure about what was going on.

I asked if she wouldn't mind checking on the table to let me know her thoughts. So the waitress went to the table, said a few quick words, and came back to me. Out of earshot, she said, "Yeah, I think we have to get her out of there". It was clear that this man was threatening to harm her when they left the restaurant.

We let the manager know what was going on. The guy had booked his table, which was good. We had his name. Outside at the taxi rank, by some miracle, there was a female cabbie in the line. I ignored the protests of the other drivers. I hopped in, told the cabbie the situation, and offered her $20 to wait around the back of the restaurant.

I said, "Please don't wait for a destination, just drive, something's really wrong with her date". The cabbie said she didn't need the $20. So then we put our plan in motion. We had the front desk call the man over to the phone, claiming he had an "urgent call". This would delay him. But there was a snag: He was trying to figure out what the "call" was.

So then my coworkers announced that he had just won a free meat tray in a raffle. Luckily, prizes like that actually were raffled off at various intervals throughout the night, so the excuse was totally believable. "Just wait here while we fetch it for you!!" As soon as the creepy guy was out of sight of the table, I asked his date if she needed to get out of here.

She just trembled and nodded. Figuring that she probably wasn't in the mood to trust a male at that point, my waitress friend escorted her through the kitchen and out to the waiting cab, where she slipped away as quickly as you please. The guy eventually came back to an empty table, and the staff just acted oblivious when he asked where his lady friend had gone.

We didn't get much of the story, other than the fact that the lady had been set up on a blind date by a mutual friend who told her that this guy was nice.

Waiters Saw Disaster Dates factsShutterstock

25. Guest-zilla

When I was 16 years old, my aunt was organizing a wedding buffet and hired me for the night as a waiter and helper. I was attending the back tables when a woman who had too little clothing and too many drinks yelled out, "You should have married me instead! Screw this loser!" She then ran over to try and fight the bride.

She literally pulled her hair, threw a drink at her white dress, and tried to hit her in the face before a bunch of guests pulled her away.

Waiters Saw Disaster Dates factsShutterstock

26. Ambushed

I worked at a fancy restaurant, so I have seen a lot. The worst was when this guy got down on one knee to propose to his girlfriend...just in time for the "other man" to walk in. Yep, right in the middle of his proposal, his girlfriend told him she was leaving him for the other guy. She added that the two of them had been having an affair for six months.

They had invited this poor guy out for dinner, hoping that telling him in public would prevent a nasty confrontation. The two of them then left him at the table, sticking him with a $200 bill. The staff who witnessed this felt awful for him, so we all pitched in to pay it. We even bought him a couple of drinks. I hope that things have gotten better for him.

Waiters Saw Disaster Dates factsShutterstock

27. Keep Cobb and Salad on

I was a waiter at a pretty high-end hotel restaurant. It was about 3 PM, and I was the only one on the floor, as it was normally very slow at that time. There was only one party seated and it was a middle-aged man and woman. You could tell that they weren’t married. I went over and asked if they wanted anything to drink, and they both got mimosas.

I went back with their drinks and asked if they were also planning on ordering food. They said yes, but that they were in no rush and would let me know when they were ready to order. About 15 minutes later, this man shows up at the front desk, starts looking around, yells “I KNEW IT! YOU DIRTY LIAR!,” and starts walking towards the couple sitting down.

The woman stands up and the guy remains seated. It became clear that the woman was having an affair with another man, and that the husband came in to confront them. He grabbed her hand and walked her out, but not before very loudly telling the man to “Stay away from my wife!” The man remained seated at the table, turned to me, and waved me over. I go over, and he says in a perfectly calm tone, “Cobb salad, please".

Waiters Saw Disaster Dates factsShutterstock

28. Bathroom Break

I once caught a couple getting intimate in the washroom stall at a restaurant where I used to work. I politely asked them to stop, but had to stand there and wait for them to finish. Once they finished, they sat back down at the dinner table. But it didn't end there. 15 minutes later, I heard the woman scream something about STDs. The man angrily got up and stormed off, leaving the woman behind to pay for her own meal.

Waiters Saw Disaster Dates factsShutterstock

29. Never Judge a Book by Its Cover

I remember serving one night, and this strange guy came in to sit at the bar. He was a little disheveled with an unkempt beard. He had trouble speaking, and he just generally seemed like someone you might imagine had difficulty socially or with dating. He had brought a bag in with him and, after he sat down, he pulled out a picture of a woman.

He stood the picture up on the counter, in front of the chair beside him, and he ordered two drinks along with his meal. One drink was for the “woman,” and it ended up going untouched. A lot of my coworkers saw it and laughed about it in the kitchen. They thought it was the most pathetic thing they had ever witnessed.

I thought something was a little off about the scene, though. Or that there was more to it than my coworkers were giving it credit for. He didn’t strike me as a desperate loner. There was an air of sadness around him, but not because he was pathetic. It felt more like grief. I talked to the bartender about it later, and he told me the whole, heartbreaking story.

Apparently, the man's wife had just passed earlier that day, and this restaurant was where they had gone on their first date together many years ago. His wife was the woman in the photo, and he came into the restaurant that night to share one last drink with her.

Waiters Saw Disaster Dates factsShutterstock

30. When Life Gives You Lemonade

I work at Panera. This guy once came in with a woman who I assumed was his girlfriend or wife. I took their order and they sat down. Maybe like three minutes later, another woman walked in. She didn't notice the other couple at first and she ordered. She also brought a bottle of lemonade with her. As soon as she spotted them, she dropped the lemonade and it spilled everywhere.

Turns out she was the wife, and the lady the husband had come in with was his mistress. So, naturally, there were some cross words exchanged and all three were asked to leave. I also had to mop up the lemonade.

Waiters Saw Disaster Dates factsShutterstock

31. He Can Do Better

I worked in a bar while I was in college, and I once had a guy come in before his date and tell me that whenever he ordered a Scotch what he really wanted was chardonnay. I must have given him an off look, because he then 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 who were more macho and that he didn't want to order a lighter drink 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. No matter what drink he asked for, I would bring him a glass of chardonnay.

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 jerk. She came in with two other women to their date. He mumbled something to me about maybe not being clear, and then, plastering a smile on his face, got on with the worst date I have ever witnessed.

To be fair, the woman was extremely charismatic. She was one of those "life of the party" types of women, while the guy was very quiet. Anyways, later in the evening, he ordered another "Scotch". He had been doing this all night. Yet this time when I brought it to the table, she insisted that she wanted to try some of it.

She said that she had never had Scotch before and wanted to see what it tasted like. It was like watching a train wreck. He tried to stop her by saying things like, "Here, let me buy you a glass," etc. Well, she took one sip and immediately knew what it was. I tried to help him by going over and apologizing, pretending it was my mistake.

Unfortunately, she still guessed the truth and started teasing him about it. Worst of all, her unwelcome friends joined in laughing as well. I felt awful and I could tell he was really embarrassed, even though he was laughing along. After a while, he asked for the bill. I brought him the tab with his and the woman's portion, but he told me he was actually paying for everyone. I felt so awful.

Waiters Saw Disaster Dates factsShutterstock

32. Tell Me About Yourself

When I was in high school, I worked as a line cook at a chain pizzeria. It was a slow Sunday morning, mostly just elderly customers coming in after church. We had one couple come in, get seated, order food, yadda yadda yadda. Then, about 30 or 40 minutes later, I suddenly hear shouting coming from the dining room.

Apparently, this couple had selected our little franchise as the place to sort out their differences and try to discuss things in a civil way. It stayed civil for a very short time. The guy got up to leave, but then realized that they had unfortunately shared a single car to get to the restaurant. So, he did the logical thing—just kidding, the next thing he did was psychopathic. 

He used the store phone to call law enforcement’s non-emergency line and ask them for a ride home. Great move, genius! Soon, a bunch of officers showed up.  As far as I know, they did not end up giving that man a ride home. Instead, they gave him a civics lecture on what the roles and duties of law enforcement officers do and do not entail.

False Accusations factsShutterstock

33. I’m Outta Here!

A couple was sitting at the bar during what seemed like a first date. I was in the kitchen rolling silverware when, all of a sudden, the dude comes busting through the door into the kitchen. He asks if there is a back exit that he can take to leave without being seen. He then sees the exit sign and bolts out the back door. I have a strange feeling this was not a successful date…

Waiters Saw Disaster Dates factsPikrepo

34. Skipping the Small Talk

I once had a couple who asked to be seated on the patio, and chose the furthest table away from the other guests. I went over to greet them with a smile and some good energy. The woman just locked eyes with me and said, "This is not going to be a fun evening". The guy with her then tried to order a margarita, and she said "You can have a Coke".

She proceeded to order an expensive drink for herself, and then they both got burgers. I went in to tell the hosts not to seat anyone near them, and for the next hour, this woman laid into the guy while he sat there and took it. Clearly, he had screwed up in a major way, based on the snippets I heard whenever I walked by.

She was explaining to him in great detail that whatever he did was wrong, that he had lost her trust, and that their relationship was now over. She was incredibly civil, unflinchingly polite, and so confident. She finished, handed me her card, and walked away with him still at the table after she left me a solid 30% tip. She was awesome. I want to be her when I grow up.

Waiters Saw Disaster Dates factsShutterstock

35. Finger-Lickin' Bad

Let me tell you about this one couple I once observed on a date. They were an elderly couple, probably in their 70s. The guy looked pretty humble, and the lady was completely dressed up. Bedazzled dress and everything. They had been flirting pretty hard with one another during their appetizer and, when their dinner came, that’s when everything got out of control.

The man took his shoes off and was teasing the lady’s legs with his toes. Then, the lady took her shoes off too and, after a good round of footsy, the guy decided to massage her feet with his bare hands while they were both eating finger foods. I’ve never choked so hard in my life as when I first realized what was going on.

I swear I could see him rubbing his fingers right in between her toes. I just can’t imagine how anyone is able to do that whilst simultaneously stomaching their food.

Waiters Saw Disaster Dates factsShutterstock

36. What Do You Recommend?

My story takes place in a really lovely, cosy steakhouse during dinnertime. A couple came in, obviously on a first date. The woman looks over the menu, quietly closes it, and reminds the man that she is vegetarian. The menu is very much built for carnivores, which I think is fine given it's a steak restaurant. But the man's reply stunned me. 

He responds with, “That’s okay, because we’re both getting the kids’ menu macaroni anyway". He went on to explain that this kids’ menu macaroni is “so, so good,” and insisting that she order it. Her face fell. This was a very serious-looking woman who clearly went all-out for this date in terms of her attire and all.

She was also much more attractive physically than he was, and clearly did not expect to be eating a bowl of macaroni for dinner. Nevertheless, she was very polite and didn’t voice any objection. They ordered the macaroni and barely said a word to each other all night. The staff could hardly keep from giggling while watching this play out.

Worst Dates factsShutterstock

37. Table Talk

I once witnessed a horrendous restaurant date. It was a man and a woman, and the guy was just...something else. These are some of the topics he chose to discuss with his date: Why evil isn’t that bad after all, a very long-winded story about how he does not have herpes, and a diatribe about how to judge the quality of a bench.

This was followed up with a few more equally ridiculous stories. He then asked her to pay for dinner and promised to Venmo her afterward. I think they ended up splitting the bill. The man was also so loud that it was impossible not to hear everything he was saying. I felt so bad for that girl. She seemed miserable.

Valentine’s Day Disasters FactsShutterstock

38. Bargain Hunter

I remember Valentine's Day 2019 like it was yesterday because of one particular couple. I'm a bartender and waitress at a chain pub in the UK. So basically, we serve pub grub. Our main clientèle is our regulars, who usually only want pints of bitter. Also important to note is that out of our 50 tables, we only have one booth. Naturally, everyone wants to use it.

So Valentine's Day 2019, we have quite a few bookings, including some for the booth. That table is booked pretty much solidly all night. All night long, it would be a matter of couples finishing food, table getting cleaned, and then next couple being seated right away. So it gets to about 8 or 9 pm and this couple walks in.

The guy asks to be seated in the booth and is told that it's booked all night. He gets a bit rude about that and asks for a nice table with table service. Dude, this is a city center chain pub. There aren’t any nice tables! His date says she's going to the toilet and walks off. He then proceeds to explain that he's planning on proposing and wants it to be special.

Again, this dude is expecting big things from this place, but we don't say anything other than that we can set him up a table in a closed off area. One of my coworkers manages to find a really tacky tablecloth, fills an empty Orangina bottle with fake flowers, and sets them out some cutlery. This is already above and beyond what normally happens at this place.

We don't usually do table service, but the boss wanted to make a good impression. So guess who received that task for the night? Yours truly. I go over to take their order and she says she'd like a sirloin steak. Before I can ask her how she'd like it cooked, he interrupts and asks her to get something from the discount menu.

She looks annoyed. Clearly, this is strike two for this guy and it's going terribly. She asks why he didn't tell her that before she looked at the menu. He says, "You know I like to save money, why would tonight be any different?" She looks like she's about to walk out, so I offer to give them a few minutes and take my leave. Honestly, I was just kinda glad to be out of there.

I go back over after a few more minutes and they order off the discount menu. The food comes out quickly. They eat and then he orders a drink. Since it's Valentine's Day, we really push the boat out and put a strawberry in the glasses. Now is probably a good time to mention that at certain points during the night, most of the staff have been standing in the kitchen listening to me tell them about this couple's disaster of a date.

We're all just waiting with bated breath to see how this train wreck is gonna end. Then comes the big moment. I'm just going over to see if they'd like dessert and I see him going to get down on one knee. So, I grab another waitress on shift and we start watching from the corner. This is where he makes his final mistake.

It appears he had purchased a toy engagement ring rather than a real one. He was hoping that she wouldn’t notice, but he forgot to take the price tag off. It said £1…She asked if he was serious. He said yes. She asked why he would propose to her with a toy ring. His awful reply? He said she knows he likes to save money.

She picked up her glass and walked straight out of the pub. I did not stop her from taking the glass. At that point, I felt so bad for her that I just decided to let it slide.

Waiters Saw Disaster Dates factsShutterstock

39. From Bad to Worse

During my travels, I ended up waitressing in an Italian restaurant in Mexico for a few months. I was once given a table where a customer was planning on proposing to his lady. Thirty minutes into the dinner, I noticed that the lady was a bit tipsy. The guy asks me to bring out a special drink, which we had agreed earlier would be the sign for when he was ready to pop the question.

He had hidden a ring inside the bottle for her to discover as a surprise. I brought the bottle out and he smiled. Sadly, this was to be the last smile on his face for the entire evening. The nightmare was about to begin. They made a toast, began drinking, and the lady almost immediately began to choke and turn blue.

That was when it first dawned on me that perhaps hiding a ring inside someone’s drink might not have been the smartest idea in the world…She began coughing. The man performed the Heimlich maneuver to save her. The ring came flying out of her throat, and let’s just say she was not a happy camper. Everything went downhill from there.

From what I could understand of their conversation, they began fighting and screaming in the restaurant. The lady insulted the guy, pointed at the glass, and wondered who put a ring inside. The man attempted to apologize. Still in her tipsy state, she didn't realize it had been his doing and that he was trying to propose to her. So she destroyed him with one sentence.

She blurted out "Whoever put that thing in my glass is probably a better lover than you. Maybe it was [insert name of man she had been having an affair with here]". The guy went totally silent and looked devastated. That was when the woman appeared to realize her mistake. She now attempted to fix things and apologize. It didn't go well.

In the process, she accidentally tripped and pulled the entire table cloth onto the ground as she was falling. All of the plates, cutlery, glasses, and bottles came crashing down. The man walked out of the restaurant at this point and she started chasing after him. I'm now left with a mess of broken and spilled stuff all over the place...and an expensive silver ring with a diamond on it.

The man came back the next day to get his ring back, and he thanked me for keeping it safe. If you are going to cheat anyway, you might as well just break things off with your partner to prevent a disastrous mess like this.

Waiters Saw Disaster Dates factsPixabay

40. A Horrifying Experience

I used to be a waiter at Olive Garden. One time, a couple was there on a blind date. At one point, the dude went to the bathroom and didn’t come out. Thirty minutes later, an ambulance shows up. He had apparently taken something in the bathroom, overdosed, and passed. The girl was traumatized. Yeah, we all went home early that day.

Wedding Objections factsMax Pixel

41. Acting Their Age?

I worked in a fancy hotel that is almost on the beach in SoCal. This area is also somewhat of a “party town,” but still an incredibly rich and nice place to live. That day, I was the hostess for the outside restaurant and had just seated three older guests, one man and two women. They were all in their 70s. The guy had a huge mustache and was wearing bright colors.

He was very obviously trying to show off his gold jewelry. One woman was wearing orange lipstick and a short white skirt. The other was wearing a dress with a huge hat. They were the only table there. It was super slow and I was there almost alone. For the first twenty minutes they were there, everything was pretty normal.

Then, one of the women stood up and asked me where the bathroom was. I told her where to go, then went back to my crossword puzzle. The hostess stand was super close to their table, and I kept hearing quiet giggling behind me. I turn around and see that the guy has half his hand up the other woman's dress and that they’re intensely flirting a few inches away from each other's faces.

I immediately turn around and, soon after, the first woman comes back from the bathroom. After a few minutes, the other woman gets up and goes to use the bathroom. And, again, I start to hear quiet giggling behind me. I turn around and he now has his hand up her skirt and starts flirting super intensely. This freaking old man player!

The other woman comes back and I try to mind my own business. They kept drinking more and more and getting louder and louder. This went on for another five minutes, when they all suddenly became super quiet out of nowhere. I turn around and am met with the skirt lady’s orange lips barreling in toward my face with her arms outstretched toward my head.

I had no time to react. I tried to turn my head as fast as I could, but her orangey kiss landed on the corner of my lips and face, leaving her mark. Seeing my stunned face, she recoiled quickly and said, “Don’t worry, it’s ok! It was just a dare! You have soft skin though!” I was silent. Then, she runs back to her table and her friends start laughing uproariously.

Waiters Saw Disaster Dates factsShutterstock

42. Standing up for What’s Right

This happened when I was around 18 years old or so. I am mostly Native American, which is an important factor to the story. A guy and his date got seated in my section, and he immediately asked to speak to my manager. This was before I even took their drink order, so I was perplexed but went and grabbed him right away.

The dude then asked my manager for a "nice white server instead". Right in front of me, while giving me a rather disgusted scowl. The girl was so horrified by this that she stood up and said "Oh no, you don’t! That kind of behavior doesn’t fly with me, honey. You can sit me at the bar. Sweetheart, this date is over". The manager made the man leave and comped his date's food.

She left the manager a $100 tip for me, with a note that said "You are beautiful and worthy of respect. Always remember that". Her date was a disaster, but she made my night.

Customer Service FactsShutterstock

43. Adults Do the Darndest Things

Couples fight in restaurants a lot. Either that, or maybe they just argue everywhere. I couldn’t say. I worked as a waiter for years and I could not even begin to count the number of wild arguments I saw between couples. But one guy comes to mind above all of them. I still can’t believe I actually witnessed this.

This guy must have been about 50 or 60 years old, and he got angry with his lady during dinner. He actually threw a full-on child-like temper tantrum in the middle of the restaurant. He stomped off away from his table and began wandering around the room, looking back at her and scowling. Even most children aren’t usually this dramatic! It was nauseating to watch.

Waiters Saw Disaster Dates factsShutterstock

44. Down by the Riverside

This was probably about four years ago, in a joint called the Esquire Tavern on the Riverwalk. We had a street entrance as well as a river entrance, but from the river you had to walk up a really narrow metal staircase to our balcony. It barely had enough room for five small tables, including one that was tucked away in a corner that made it hard to see from below.

Anyways, it was a slow summer lunch hour, so I was doubling as a hostess. This guy comes up from the river entrance and asks for a spot on the patio, specifically the hidden cramped one. “No problem sir,” I say, and I go get him set up. We chat for a bit. I take his order, bring it out, and go about my business, which was to passively watch him through the window because he was my only table and I wanted to keep an eye on him.

I started to notice him suddenly ducking his head, as if he was trying not to be seen from the river level by someone. I remember pointing it out to another co-worker, who was just as curious as I was. Then, we suddenly heard a woman scream, “There you are, Marco! You piece of trash!” I could hear the staircase shuddering as someone was clearly stomping their way up it.

My coworker astutely dipped out to find the manager. Meanwhile, the lady started laying into this dude, and all I could make out was something about him ditching her. All the while, he was just ignoring her and calmly eating his buffalo burger, which only made her snap completely. She slapped the heck out of this dude, telling him to "acknowledge me right away!"

He then simply got up, walked around her, and came inside to sit at the bar. She then sat down and started eating this man's meal like nothing was wrong. By this point, the manager had arrived. He went outside and started trying to kick this woman off the premises for the disturbance. Meanwhile, I went to go talk to Marco and take his dessert order. Who knows what that was all about...

Valentine’s Day Disasters FactsWallpaper Flare

45. Not Part of the Plan

I once watched a proposal in the dining room of the hotel where I used to work as a waiter. Everyone was eagerly awaiting the dessert and ring box to be brought out. She saw the box and immediately started shouting “No, no, no, no, no!” before the guy even had a chance to pop the question. She then told her crushed would-be groom that they needed to talk.

People who had initially been clapping just slowed to a silence. She ended up going back to the room, collecting her things, and leaving, while he cried at the table for a few minutes. It was a super depressing scene for all of the staff, guests, and that poor guy. I wouldn’t wish this experience on anyone.

Susan B. Anthony factsShutterstock

46. A Case of Mistaken Identity

I used to work at a bar where at least 70% of the customers were there on Tinder dates. There was a line of two-person booths along the wall when you first walked in, and one day there were two dudes sitting by themselves in two different booths. Both of them were facing the door. One was in the first booth, one was in the last booth.

This girl comes in and walks up to the first booth. She says hi to the guy and sits down with him. They are chatting for about five minutes when the other guy, who is still sitting by himself, comes up to her and says “Hey, I’m so-and-so. Aren’t you so-and-so?” They all talk for like 30 seconds, and then she gets up and goes to sit with the other guy at the last booth.

Eventually, a different girl shows up for a date with the guy at the first booth. I don’t know exactly what happened, but I laughed my head off watching it all unfold.

Valentine’s Day Disasters FactsShutterstock

47. Taking up Space

One time while I was working as a waiter, the place was getting extremely busy. At the same time, these two 15-year-old lovebirds had been sitting at a table for several hours and only ordered one milkshake. As much as I didn’t want to spoil their fun, I had to politely ask them to leave. It was clear that they were just looking for a private spot to hang out together away from their parents, and had no intention of actually ordering a meal.

Waiters Saw Disaster Dates factsPixabay

48. Distracted Dining

I once saw a couple who literally spent their entire dinner time without talking to one another. Not even a single word. They were just constantly staring at their phones. This doesn't necessarily mean that they are in a bad relationship, but it makes me sad for some reason. Either way, it’s hard to argue that this particular date was a good one…

Waiters Saw Disaster Dates factsShutterstock

49. Toe Be, or Not Toe Be

I work at a small bakery in my town, and I was there when this all went down. It was around two in the afternoon. The day had been normal so far, but then suddenly I saw the retail staff gathered in a huddle by the door. As soon as I had an opportunity, I went to go see what was did not disappoint.

Apparently, a couple had come in on this summer day, ordered two bowls of soup, and sat down. The waitress took their order, went to the back, and started to prepare their soup for them. She then brought the food back out to them—only to discover that, in the time it took for her to get the soup, the woman had taken off her shoes and placed her leg on the table. Oh, but that wasn't the worst part. 

The guy was now sucking on this lady's toes in the middle of the restaurant! The waitress didn't notice until she went to place the soup on the table. She stood there in shock, and the couple was oblivious to her presence. This guy was really going to town, and the lady was starting to moan by the time they realized that their soup was ready. That couple is no longer allowed in.

Fastest Quit Job FactsShutterstock

50. A Happy Ending

A guy once reserved a private room in the very fine dining establishment that I work in. The plan was dinner for two, champagne, and a proposal. He gave us instructions to bring the champagne out when she said "yes". By mistake, I poked my head into the room a little bit early, just to make sure I hadn't missed the big moment.

The guy spotted me holding the champagne bottle in the corner, thought that I had ruined his plans, and had a full-on panic fit. Within a few seconds, he threw up all over the table. Naturally, his girlfriend was very concerned and rushed to his side to see if he was okay. He immediately jumped up and shouted, “Screw it!”

He pulled out the ring, dropped down on one knee, and proposed right then and there, with his fresh vomit still covering his clothes and the table. She burst out laughing, said yes, and kissed him on the head. I got them a new table in a different room and served champagne. Honestly, it was great. I hope I find love like that one day!

Waiters Saw Disaster Dates factsShutterstock

Sources: Reddit,


The Yawn-Inducing Hall of Fame: Top 15 Most Boring Jobs

Take a humorous dive into the top 15 most boring jobs in the world. From watching paint dry to counting cars, discover the less-than-thrilling day-to-day of these necessary, yet yawn-inducing roles, along with what they entail and what they pay.
November 14, 2023 Allison Robertson
worst employees

The Worst Types Of Employees In The Workplace

Navigate the minefield of workplace dynamics with our guide to the worst types of employees. From procrastinators to gossip mongers, discover why these characters can disrupt the harmony of any workplace and how to handle them effectively.
November 27, 2023 Sammy Tran
Gerald Ratner Editorial

Doing A Ratner: Honesty In Business And The £500 Million Gaffe

Gerald Ratner built a massive jewelry empire from the ground up by himself—then, in just a matter of minutes, he destroyed it all.
January 19, 2024 Samantha Henman

These People Shared The Worst Moments Of Their Lives…And They’re Utterly Brutal

From cheating spouses to catastrophic accidents, there are times when life throws brutal punches...and these people have firsthand experience.
March 1, 2021 Eul Basa

World Travelers Share Their Best Travel Tips and Tricks

Being a savvy traveler is something that only comes with experience. These frequent flyers share their best tips and tricks to help you travel seamlessly. 
November 15, 2019 Eul Basa

Dear reader,

It’s true what they say: money makes the world go round. In order to succeed in this life, you need to have a good grasp of key financial concepts. That’s where Moneymade comes in. Our mission is to provide you with the best financial advice and information to help you navigate this ever-changing world. Sometimes, generating wealth just requires common sense. Don’t max out your credit card if you can’t afford the interest payments. Don’t overspend on Christmas shopping. When ordering gifts on Amazon, make sure you factor in taxes and shipping costs. If you need a new car, consider a model that’s easy to repair instead of an expensive BMW or Mercedes. Sometimes you dream vacation to Hawaii or the Bahamas just isn’t in the budget, but there may be more affordable all-inclusive hotels if you know where to look.

Looking for a new home? Make sure you get a mortgage rate that works for you. That means understanding the difference between fixed and variable interest rates. Whether you’re looking to learn how to make money, save money, or invest your money, our well-researched and insightful content will set you on the path to financial success. Passionate about mortgage rates, real estate, investing, saving, or anything money-related? Looking to learn how to generate wealth? Improve your life today with Moneymade. If you have any feedback for the MoneyMade team, please reach out to [email protected]. Thanks for your help!

Warmest regards,

The Moneymade team