Romance is in the air! Going to a nice restaurant for a nice date is a classic go-to for most lovebirds. Servers get to witness firsthand every fumble as timid couples get to know each other or express affection toward one another, but what happens when a date goes terribly wrong in their presence? In these stories, servers reveal the most cringe-worthy dates they’ve ever seen unfold.
All stories have been edited for clarity.
“Soulmates”
“I work at an Italian restaurant in the good old state of Missouri.
One day I had three people, two girls, and one guy, seated in my area. One of the girls and the guy were obviously dating with how touchy-feely they were, and the other girl that was there was just third wheeling it.
The trio started talking and the guy’s girlfriend shared with me how great her boyfriend treated her. She went on to talk about how she dated a lot of bad dudes before him and she really believed he was her soulmate.
I thought her backstory was quite touching and the guy seemed to think so too. The girl then told me they’d been dating for a year and a half and how they were out celebrating their anniversary that day. They had chosen to celebrate it at my place of work because it was their favorite place to eat and she brought her best friend along to celebrate with her.
The other girl sitting at the table smiled sweetly at me.
I was so happy to see how happy they were together. I had recently gone through a bad breakup and felt so compelled at seeing true love again that I went to the back and offered to pay and get them a free dessert. As I was at the bar of this restaurant, I pointed at them and explained what I was told to the bartender when the blonde gets up to go to the bathroom.
Then the guy and her best friend just have at it.
They were over each other the minute that bathroom door shut. The two were running their hands all over each other. I couldn’t believe it. When the guy turned and saw my obviously horrified face. I heard him say, ‘Crap, he saw us.’
His girlfriend exited the bathroom and I quickly rushed to tell her what I saw when I heard her boyfriend exclaim that his mom just called and he had to go.
Before I knew it, the boyfriend and her ‘friend’ dip out before I can catch up. I genuinely couldn’t believe what I saw happen and it hit me hard the rest of the night.
The poor girl came in a week later for a drink and to socialize. The bartender and I told her everything. She had a lot of drinks that night.”
Coldhearted
“A married couple came in one busy weekend night on a date. I wasn’t their server, but the server was telling me how this married couple was arguing throughout their dinner and it was extremely awkward.
So I, along with almost every other server in the building, kept an eye on them. The husband kept ordering drinks for his wife and ordered more whenever she went to the bathroom. She appeared to have no self-control and got extremely drunk.
Then it happened:
In the middle of the dining room, on a Saturday night, the husband announced to his wife he wanted a divorce.
Awesome timing.
So the wife, drunk, broke out in tears and started screaming at him in the middle of the dining room full of patrons. Everyone stopped what they were doing and stared at the enraged woman until she stampeded out of the restaurant.
The restaurant I worked at was in a very posh, upscale area and had full floor-to-ceiling glass windows where you got a full view of everything happening outside. So the drunk soon-to-be ex-wife stormed out of the restaurant and nearly slammed into the all-glass front door. This however did not bother the drunk woman. She continued to walk for a minute on the sidewalk and decided to cross the street. Going too fast, she slipped, fell, and nosedived into the concrete.
A bunch of servers stopped what they were doing and ran outside. There was blood everywhere. She had busted her lip and chipped her tooth. Blood was all over her face. The woman kept screaming and everyone was freaking out. We tried to call the husband over.
Unbothered, he literally said, ‘She’s not my problem anymore,’ and casually walked away.
An ambulance was called, and within a few minutes, our entire dining room looked like a rave because the flashing lights were illuminating the entire inside of our dark restaurant. The woman was crying and screaming the whole time. Eventually, the husband came back to pay the bill. He looked at his ex being hauled into the ambulance, shook his head, and walked away.
This was about five years ago and I will never ever forget it.”
Oh, There You Are!
“I used to work at a pub back in the day.
One evening a guy came in and sat down at a table for two. I asked him if he wanted a drink to pass time while he waited for whoever was accompanying him for dinner. He casually nodded and ordered a drink. Soon after, the man told me that he was waiting for a girl he was meeting for a date.
The man was waiting for a while, but I served him a couple more drinks as he requested. Before I knew it, an hour had passed. The man was looking at his phone occasionally, still drinking.
Finally, the man came up to the bar after an hour and a half. With a sullen face, the man announced that thinks he’s been stood up.
‘That’s rough, man,’ I said sympathetically.
The man continued to order a couple of drinks and pounded them back. In no time, the man was starting to look and sound considerably worse for wear at this point. He ordered a couple more drinks but I politely told him I would have to cut him off.
However, the man convinced me to get them for him by telling me he was going to drink them and leave. So he downed the last drink I served him and got up to leave.
As he was hobbling over to the door a miraculous change of events took place that caused him to freeze in his tracks.
In came a disheveled woman still wearing scrubs. She apologized up one side and down the other for being late.
I then got to serve one of the most awkward dates ever. The guy was awfully drunk. I probably shouldn’t have given him the last drink he requested but I was simply trying to accommodate the guy for having been stood up, or so we thought.
He and his date made some small talk but the entire exchange was terribly awkward. At some point, the man got up and went to the bathroom.
Twenty minutes went by and he never came back. Finally, one of the male servers walked up to his date and told her the guy was having some trouble in the bathroom.
He was sitting on the toilet bawling and vomiting.
In the end, we asked her to get him out of there.
We called him a cab and she pretty much shoved him into it and ran.”
Caught Red Handed
“I was a server at a very upscale French restaurant in New York City.
One evening a middle-aged man and a young woman sat in my section, clearly on a date. You could tell the woman was his mistress by the way they interacted with each other.
The two of them were high maintenance but pleasant enough. Right after they received their entrees, I saw the man look across the restaurant at another table. All the color immediately evaporated from his face.
His date also noticed and turned to see what he was looking at.
The man’s wife was at another table. Crazy enough, she was also on a date with her side piece, on the other side of the restaurant.
The wife made eye contact with him and had the same expression on her face, which very quickly turns to rage. She briskly walked over to his table and started whisper-yelling at him and pointing her finger right in his face.
The husband started to do the same back at her. It was a very ugly sight to see. The restaurant wasn’t very big, so everyone knew what was going on. Despite their best efforts, their harsh exchanges made the atmosphere icy.
The husband’s date stared hard at her plate, absolutely mortified. The wife’s date, however, pretended nothing was happening and continued eating. Eventually, the wife stormed back over to her table and wolfs down her dinner in a rage. The husband sat back down with his mistress, but she didn’t speak to him for the rest of the meal.
It was a fine-dining restaurant and the two of them had ordered multiple courses. Having to clear, crumb, and reset their table two more times was less than fun. The husband still left a very big tip and apologized on the way out.”
On The House!
“A couple was having a flirty date at a table close to my bar. They were on their second round of drinks and seemed like a very loving couple full of laughs, kisses, and crazy flirting.
A little later in the night, a lady came in and sat down at the bar. Right away, I noticed that she seemed off. The lady stared at the bar menu for a good five to ten minutes. The menu, however, was upside down.
After studying her actions, I quickly figured out she was watching the couple behind her through the bar mirror. Curiously, I sauntered over to greet her.
As soon as I got close, I could see she was wearing a wig. A terrible one. The woman took off her sunglasses and set them down on the bar as I began to strike up a conversation. Her eyes were puffy and tears were streaming down her face.
At that point, I was intrigued. I immediately offered her a drink and asked her what was going on.
It turned out the couple behind her was actually her husband and his mistress. For the next hour, I had to give her a play-by-play of her husband’s date. Awkward was an understatement. The woman was devastated but kept pushing me to get more details.
Then the woman slid me forty bucks cash and requested I send them over another round of drinks.
‘What the hell?’ I thought but quickly shrugged it off because I would have been left with a twenty-two-dollar tip afterward. I sent the drinks to the table with my compliments. The husband and his mistress waved their thanks. Later, his wife does it again. She calmy slid another wad of cash in my direction to cater to her husband and the mistress. I sent over the drinks knowing the couple would be drunk at this point.
Eventually, the couple finished up and left. They even stopped by the bar on their way out and the husband shook my hand, and said, ‘thank you.’
He didn’t even recognize his wife sitting right there at the bar. He hobbled out of the bar holding his mistress by the waist.
Then I got to witness the wife’s plan unfold. It was epic.
His wife pulled out her phone, called 911, and reported her husband as a drunk driver. She gave the dispatcher his car description and license plate number and said he was on the exact road she knew he would take home.
Her actions were, but he deserved it. It would be his fourth DUI so, prison time was probably in his future.”
For The Love Of Ketchup
“I work in a restaurant where we make our own ketchup. Not everyone likes it which is fine. As long as people are nice about it, I actually have a secret Heinz ketchup bottle guests can use just as long as they don’t tell anyone.
A woman was seated at my table looking super excited. I asked out of curiosity what the occasion was. She proceeded to tell me she was on a blind date. The woman then ordered a glass of wine and waited anxiously. I honestly thought it was cute.
A short while later, a dude showed up with his eyes glued to his phone. He completely ignored my hostess, and eventually found the beautiful woman waiting for him.
The man, however, continued to text and talk on his phone for roughly fifteen minutes. When he finally hung up, I went to the table to wait on them.
The guy tried to order for her which obviously embarrassed her. Once it was his turn, he ordered a well-done steak and fries. When I brought it to him he asked for A1 steak sauce and ‘REAL’ ketchup.
When I informed him we had neither he grunted and said he had ketchup packets in his truck. As soon as he walked out the door, the mortified woman asked for her half of the check and her food to go. I helped her leave out the side door before he could even come back.
It was awkward serving him after that. He used seven ketchup packets.”
Eternal Love
“One time we had a middle-aged lady come in with a gentleman. Even though it was just the two of them, they asked for three menus. I went over to the table to introduce myself and ask if they were waiting for one more.
The woman said, ‘No. My husband is here.’
Then the two ordered drinks and an additional glass of water.
When I came back to drop off the drinks her ‘date’ was in the bathroom. The lady explained to me that her husband had died a few years ago and the man accompanying her was a friend who kept asking to go out.
So, she said yes but insisted her DEAD HUSBAND come with them. This is why they had three menus. She instructed me to bring her husband up as often as possible, pretending that I knew him and making sure I ask if he was having anything for dinner when I took their dinner order.
She would refer to ‘her husband’ as if he was sitting right there. I then heard her tell the other guy all night that he tried too hard and that he was kind of mean to her.
I do not miss working in the restaurant industry.”
Not The One
“I was managing at the time and had a lady in her mid-forties compliment me.
She was not an ugly woman by any means, but she wasn’t overly attractive either. She was super excited to be going on a blind date and showed up early. She sat and had a glass of wine while she chatted up my bartenders, servers, and myself.
We all really liked this woman. She was super sweet, friendly, and seemed to really be trying to have a nice time. That all quickly ended when her date showed up.
Her date came in about a half hour late and was talking on the phone. He casually sat down next to the woman and continued talking, completely disregarding her. When he finally got off the phone, her date nonchalantly went over to the bar to get a drink which was odd to say the least because my server would’ve done it for him. The man then proceeded to order a drink from the bar, downed it, then ordered another drink before he plopped down in front of the woman.
The woman tried to have a conversation with him but he was constantly looking around the room like he was seeing if there was anything better for him to be doing. When my waitress took their order, he asked for his food to go. As soon as his food came out, he grabbed it and completely leaves the poor woman dumbfounded at the table.
The man tried to say something to me about how the woman was not attractive and he had to get out of there. He tried to get me to agree with him, but I just rolled my eyes at him and walked away.
The woman was devastated and cried silently at the table. My entire female staff was at the table trying to console her. I was going to let her hang out there all night and get whatever she wanted on the house. but the woman was too upset and left shortly after.
That guy was such a douche. That woman was such a sweetheart. It really angered me how he treated her.”
Double Whammy
“I’m not a server, but used to be a DJ on a dinner harbor cruise. One time, a guy who I assumed to be in his forties had a decent amount of cash so he upgraded his regular dinner date to include a special table and event coordinator, dinner for one of his buddies to be a videographer, and to get his own special dance with his girlfriend to start off what should have been dance time for all the guests.
He also arranged to have two dozen roses waiting on the table when they arrived, plus a treasure chest filled with seventy-five more for a total of ninety-nine that was supposed to be brought out by the coordinator and another member of the serving staff at the end of the aforementioned dance.
Once that took place, he was then supposed to propose. I was informed of the plan ahead of time because as the DJ I needed to welcome them out to the dance floor for their special dance after dinner and make sure the rest of the guests did not interrupt.
So the couple showed up and the girl looked like she was probably fifteen if not twenty years younger than the guy. The evening went as planned, right up to the part where the song ended and the older man slowly got down on one knee, takes her hand, holds the ring at the tip of her finger, and asked her to marry him. The girl, however, just stood there. The music stopped completely. The event coordinator and server were still holding the roses. The guy’s friend was still filming. Basically, everything was at a standstill. The younger woman continues to just stand there, unmoving, without giving a response.
There were a good sixty to eighty people on this level of the boat sitting in uncomfortable silence watching this unfold.
I can’t say for sure how long it went on. It could have been thirty seconds, or it could have been five minutes. Every so often the would whisper something to her, but his date was frozen like a deer in headlights. Eventually, she let him slide the ring onto her finger, and then they slunk away back to their table.
Now, here’s the icing on this tragic cake of awkwardness.
I was talking to a server afterward and they told me they had a guy at one of their tables tell them at the beginning of the night that he was gonna propose and ordered the ‘celebration’ dessert.
Well, dessert time rolls around a while after the above incident, the waiter brought out the dessert and said ‘congratulations’ as she set it on the table. The woman at the table looked confused and the man gave the quickest of headshakes.
The waitress acts as if she’s confused about tables and just sets the dessert down and walked away. The first guy’s proposal went so bad, it scared the second guy off. So in hindsight, he managed to blow two proposals in one night.”
You Got This?
“I work at an ice cream parlor.
A couple of years ago I had a couple come in. It seemed like their first or at least one of their first dates. They were nervous around each other but they seemed to go together well.
They were looking over the menu for a very long time. As they were standing at the register, they finally decided on the flavor of their choice. The girl took out her wallet to get ready to order hers. However, the guy insisted on paying. Unfortunately, they spent another eternity or two going back and forth over who would pay I waited for them to order.
They came to an agreement that the guy would pay! Thank goodness. To me, it’s always awkward standing there while people argue over this and both shove their credit cards at you and expect you to choose who is responsible for the bill.
So they finally ordered. I went to get their sundaes, rang them up, and once the guy saw the total, which was about ten bucks, he awkwardly stood there for a minute and requested, ‘Can we actually do them separately?’
The guy then turned to the girl and said, ‘You still want to pay for your own right?’
His date looked at him with the most incredulous look before she slowly retrieved her wallet back out of her bag that she had already put away when he decided he would pay.
She muttered, ‘Yeah sure that’s fine.’
Once they had their ice cream, the couple sat inside in silence for fifteen minutes. The girl was clearly no longer interested. I didn’t know who to feel bad for.”
“Poor Guy”
” I got to witness a tinder date go horribly wrong. It was their first meet and I felt so bad for the guy.
The guy showed up first and explained to me what was going on. He ordered a beer and sat and patiently waited for his date to show up. Unfortunately, his date showed up forty minutes late to their date. The worst part was she was already hammered and a hot sloppy mess.
Very soon into their date, the girl lost interest and started going around hitting on other guys at the bar. She was sitting on their laps and paying no attention to her date. It was awful and gross to see her act that way.
The last straw was when she lost one of her shoes, was walking around without it, and yelling through the bar for someone to buy her another shot. I promptly cut her off because I had only given her a single beer before I realized how drunk she was.
I split their bill because I wasn’t gonna make the poor guy pay for hers. As soon as I gave her her part of the check, she tried to tell me the other guy was paying for it, and I told her no absolutely not.
After some fuss from her, the bouncers came over and told her if she didn’t pay her tab and leave we’d have to call the police and send her to detox, so she paid for her tab and found another man to take her home.
I ended up buying that guy most of his drinks for the night because I felt bad for him. He seemed really excited about the date. This was definitely one of the most awkward dates I’ve seen.
The poor guy just sat quietly and politely at the bar while she grinded on other men.”
Way To Go, Brian!
“I was serving a couple one night. The guy seemed pretty cool to me and we clicked within moments of their date. I dropped off their appetizer and the guy automatically asked what I suggested. Shortly afterward, he started a conversation about video games.
I suggested the salmon, and they both ordered the salmon.
Now, the restaurant I worked in was a top-class sushi joint. Fish was shipped in fresh, always on ice, and perfectly fine every single time. I don’t think there had ever been a single case of food poisoning, which was pretty nice for a sushi restaurant with several years under its belt.
Well, apparently eating the salmon destroyed this dude’s stomach. He started shouting and demanded it for free, furious that his girlfriend was now going to be up all night with stomach pains from eating it.
I noticed the girlfriend hadn’t said anything and was just looking at her boyfriend with a bewildered look on her face.
Our manager sent out freshly cut salmon sashimi to prove his food was fine. Of course, the guy ate it and said it was worse than before. He then got up and left the table to smoke, but the girl stayed behind.
As it turned out, it was their first date. The girl was super pissed he left to smoke in the middle of their first date. She asked a server almost in tears if what he did was a normal thing. The girl then apologized for his behavior and said she just wanted to get out as soon as possible before something happened and to please bring dessert and the check.
Her date came back right after we dropped the dessert and check on the table. While walking away, I heard him snap at her and question why she wanted to leave. I didn’t hear the rest of the conversation, but I did watch and listened as the girl stood up, and screamed, ‘YOU’RE A FREAKING MORON, BRIAN!,’ before knocking everything off the table and storming off.
The guy watched her leave before he pulled out his wallet, paid the bill, and leave. There was only one other table in the restaurant at this time, it being almost an hour after closing. They were the only people laughing louder than us was them.”
