35 Nightmarish Dating Stories That Prove How Costly Of A Game Dating Is
Dating is tough, and anyone who says otherwise is lying. No matter how old you are or how much experience you have with dating, it never gets any easier. Sometimes, it can even be embarrassing and cruel.
Many adults choose to get to know each other over dinner. In fact, the most common date is to a restaurant for food or drinks. You might think a date like this would be pretty foolproof, but that’s not always the case.
The servers who work at these restaurants see and hear a lot of strange conversations while they are waiting tables. They may happen to be around when a date doesn’t work out and see and hear everything that goes down.
These servers have all witnessed some crazy dates. Some made the servers laugh, and some made them want to cry. Most of them will never forget these dates. Here are 35 horrific stories that show how awful dating can be.
1. That’s Tough To Watch
“I work in a four-star restaurant and one night I had a man come in for dinner sweating bullets from the time he sat down. He and the lady were obviously a couple and the entire staff guessed what would happen, especially after he ordered a $300.00 bottle of champagne to start the meal. She looked happy, but worried through the entire meal. When the dessert came, he got down on one knee and I heard her say, ’Please don’t.’
“Those two words stopped MY heart, I cannot imagine what this poor dude was going through. They had a hushed conversation and she literally ran out, while he sat there still holding an open ring box. He finished the bottle of wine they had ordered during dinner and got pretty wasted. Finally, he turned to me and asked, ‘Why won’t she let me love her?’”
This poor guy just wants to be loved.
Source: Four Nouns
2. Don’t Get The Soup
“Once I served two people where the woman wouldn’t stop picking at her scabs. Just made a pile out of them on the restaurant table. It was horrifying.
“The man excused himself to use the washroom and I brought his soup to the table. By this time the pile of scabs wasn’t there anymore. The guy came back from the washroom, saw the soup and no scabs, and decided not to eat the soup.”
Were the scabs in the soup?
Source: Sarin 77
3. A Little Weird
“I served a married couple not too long ago. The wife got up to use the restroom twice during the meal. Each time she left, the husband tried to get me to meet him for a drink. He was dead serious. The worst part was when his wife said that I looked exactly like his daughter who was away in college. I threw up a bit in my mouth after that comment.”
That’s a really strange thing to say.
Source: Cheesey Romance Novel
4. He’s Stuck
“I was waiting a table for two teenagers who were probably around 16 or so and clearly on one of their first dates. Everything appeared to be going well until the boy got his head wedged in the back of the chair. Fire brigade were called, and after 20 embarrassing minutes, he was cut free. The girl went to the bathroom and never returned.”
Poor guy was probably so embarrassed.
Source: Stick Tips
5. Keep It In The Family
“I waited on a couple on Mother’s Day, who first appeared to be mother and son. But as the night went on things got a little strange. They were sitting on the same side of the booth, being really touchy, wanted pictures together, he bought her roses. Weird stuff. At the end I had no idea if it was a young guy who just scored big time on Mother’s Day, or if it was a really gross mother-son relationship.”
Let’s hope it wasn’t the latter.
Source: Shays Days
6. Full Circle
“I once waited on the engagement party of a girl I slept with a week before. I said ‘Congratulations.’”
She was probably mortified.
Source: Sol Can Escape
7. Life Lesson
“When I was in college, I waited tables at restaurant that mainly serves chicken wings. A family of four walks in and the husband looks like a beaten man. Eyes down and slumped shoulders. The wife and kids order. When it’s his turn he asks his wife’s permission before ordering everything. ‘Can I have a Coke? Can I have 15 wings?’ I kinda laugh thinking they are joking. Finally, after ordering he looked up and asked me if I was married. I replied that I wasn’t and laughed again. The man looked at me with his dead eyes and monotone voice and said, ‘Never, ever get married.’”
He was just trying to give out some advice.
8. Exchanging Stories
“I was working at this hipster coffee shop/restaurant when a couple who were obviously on a first date sat down at the table next to me. They were really cute together, and they started off their conversation with a relatively harmless topic, like their bible study group or something like that.
“They continued on in typical first date fashion, and then the guy started talking about the time that he got arrested for motorcycle racing, probably trying to seem edgy or like he was a badass. The lady friend responded with her own story of getting arrested: She got shitfaced and was giving her bf at the time a BJ in his truck when some cops checked on them. She ended up puking on the hood of the police cruiser. Evidently, that wasn’t a deal breaker, and the guy responded by telling her about the time that he was arrested because the cops thought he was trying to abduct his little sister.”
Some people just don’t care about these things.
Source: Bele Goth
9. That’s A Hot Date
“My girlfriend and I recently went to a sushi place where one of the rolls was called the Russian Roulette Roll. It was this delicious sounding roll and the kick was one of the pieces had a ghost pepper in it.
“The waitress told us about it, my girlfriend got excited about the concept and we ordered it. I kept warning her that if she got that piece it could ruin her night but she was totally into the idea. When the roll got there one of the pieces was slightly more decorated than the others, and knowing that she didn’t understand what she was getting into I offered to go first and took that one…
“Now I was in the Marine Corps and had experienced the gas chamber on several occasions. This basically felt like that but in my mouth. It was brutal. I tried to remain calm, ate all the ginger, drank everything on the table, and was still struggling to maintain composure. She insisted that it couldn’t be that bad, so I leaned over and kissed her. She looked like she was going to pass out once she started feeling it. That was a painful night. We don’t do shit like that anymore.”
What a romantic memory.
Source: Saints Sinner
10. So Embarrassing
“I worked at a breakfast place, so we got a lot of awkward one night stands coming in. Anyway, this pair walks in and seats themselves. He orders the drinks. One water with extra lemon for the gentleman, two small orange juices for the lady.
“When I went back, he asked for more sugar and lemons. He’d used all twelve to fifteen packets of sugar (and sweet n low, and cane sugar, and equal) in his water with extra lemon.
“Every ticket I took at that place usually cost about $5-10 per person, and this guy’s ticket was at around $30, which was insane for the place. His girlfriend’s was $8, including the OJs. Time comes to pay and he stares at the girlfriend. She pulls out a card, which comes back declined. She starts crying when he says he doesn’t have money. She goes outside, calls her mom, calls her bank. She’s screaming on the phone for about twenty minutes. While she’s melting down outside, dude comes up to the register and throws down a wad of ones. ‘Here.’ And leaves.”
Maybe they should have checked the bank first.
Source: Sweet Rhyme Pure Reason
11. No Shame
“It’s late, not far from closing, and I’m sat a table of four people. Two older middle-aged women and two men in their early twenties. They all order drinks. Cool.
“One of the men disappears into the bathroom. I later find out it was to throw up. Charming. The other three are having a great time. I’m mostly ignoring them except for buzzwords that clue me into their needs.
“But then I hear one of the ladies say, ‘If you’re going to go into porn, we need to know what you’re working with!’ Out of the corner of my eye I see the young man stand up, face the two ladies, and reach for his zipper.”
He’s ready to show them what he’s got.
Source: Annie Normal
12. Such A Tragedy
“An older woman (in her 60s) sat down at the table while her boyfriend (a little older) headed to the restroom. She began to tell me how they were young lovers who had lost touch for decades. Coming together now was perfect, she said — the right time. This couple was really sweet in an end-of-the-Notebook kind of way.
“The man came back and ordered a hearty sausage on penne pasta. Halfway through his meal, he slumped over and grabbed his chest right above his stomach. This guy might have been around 300 lbs and yes, it was a heart attack.
“I called the ambulance and frantically grabbed a manager nearby to help with any kind of aid. The restaurant erupted with concern, but I was able to clear the way for a stretcher through the back door. With the guy on the stretcher, his date was in tears and cramped with horror. Her muscles tightened along her arms while her hands were clawed around the guy’s plaid shirt.
“This scene with the moody lights and rustic ambiance of Olive Garden was truly disturbing.”
Hopefully, this poor man was okay.
Source: Black Metal Coffee
13. Mommy Knows Best
“A couple came into the chain restaurant I worked at. Both looked like they were mid-30s. I go to take the order and the guys says, ‘Hold on, let me call my mom. She can tell me what I would like better.’ The lady just looked at him like ‘I messed up… I messed up real bad.’”
Mama’s boys don’t grow out of this stuff.
Source: Something Shinny
14. Good Thing He Got Out Of There
“A guy comes in with a girl, they’re in their early 20s. It looks like they’re on a first date, making small talk, etc. Everything’s fine until two more girls walk in with a toddler and sit down to join them. The guy looks a bit shell-shocked but is making nice with these people who are obviously friends with the original girl. These girls had brought Monster energy drinks into the restaurant with them.
“Soon the toddler runs out of juice in her sippy cup, so the mom fills it with the energy drink. She then lets the toddler play with the sugar container. The table is getting louder. The kid pours sugar all over the table and, high as a kite on the energy drink, starts licking it up.
“Meanwhile, the girls are laughing at the toddler’s antics and talking amongst themselves, totally ignoring the guy. He ended up eating half his sandwich and came and apologized to us for the mess and the awful people. He left a $50 and got the hell out.”
He dodged a bullet there.
15. Pooped His Pants
“First date for a couple in their late 20s. Started smoothly, the obvious first date jitters and awkwardness but nothing odd. 10 minutes later they order, and the guy is sweating bullets, really nervous.
“I checked on them about 5 minutes later and he’s looking distinctly off. He didn’t make it to 20 minutes. He pooped himself and ran out leaving the girl sitting there in shock and pretty upset.
“The story was she had been set up on the date by a friend, who’d told her that he was nice, but extremely shy and nervous. Apparently, it was all good until he needed to talk about himself, then poop city occurred. That chair went straight to the dumpster.”
There are no words for this one.
Source: Dammit Dave Not Again
16. The Nerve Of This Guy
“A couple in their late 20s was having a quiet discussion in their booth and were going from their table over to the bar to use the phone and back to their table. Then suddenly the woman yells, “YOU BROUGHT A HOOKER INTO MY MOTHER’S HOUSE, YOU D!C% !!” and storms out.
“Restaurant is dead silent, and the bartender and I just look at each other and burst out laughing as the guy shuffles back to his table.”
How could you not laugh at this?
17. It’s Magic
“A woman in her late 20s and an older guy in his 50s come in for a date. I never really saw the two talk.
“Each time I came to the table the woman asked me what the most alcoholic drink was (cocktail the first time, martini the second, and beer the third) and subsequently ordered what I told her. She was obviously using this dude for a good meal and needed to get VERY liquored up.
“Meanwhile the man was just awkwardly sitting there, sipping on his one whiskey drink the whole time either oblivious to what the woman was doing or just welcoming the idea, so he could get lucky?
“Here’s the kicker – he started performing magic tricks at the table sometime towards the end of the meal. When the woman went to go to the bathroom he gave me a playing card and told me to say that I found it in the book somehow. I obliged because he said it would merit me a solid tip, but when I acted out my part she didn’t believe me and called him a liar.”
There’s magic in the air.
Source: I Get Weird
18. That’s Not How It Works
“I used to work in an upscale fondue restaurant. The hardest part of the job is explaining cook times, keeping an eye to make sure people aren’t contaminating the plate they are eating from with uncooked meat, etc.
“Anyways, there was a couple on a date for their 10th wedding anniversary, dressed to the nines, jewelry, champagne, the whole deal. About 15 minutes after dropping the entree there was a scream. I come out to see VOMIT EVERYWHERE. Not just on the table, but projectile on the walls, clothing, EVERYWHERE.
“As it turned out, one of the couple had a seafood allergy and didn’t inform us of it. They figured that as long as they didn’t eat any of the shrimp ordered by their partner, they would be just fine while ignoring the fact that it was all cooked by them in the same pot.”
They should know better than this.
Source: Streak 84
19. A Harsh Reaction
“Did not wait the table, but I had to clean up the mess. A young couple were having dinner when all of a sudden, the guy stood up, picked up his plate of wings and threw the plate at the woman’s face and stormed out of the restaurant. Turns out she’d brought him to dinner to break things off, and he did not like that.”
Hopefully, the woman wasn’t hurt.
20. Caught In The Act
“This lady, about 30 or so, would come in every so often and meet different men. They’d get drunk and then leave together. After about 9 months of this she comes in with a bunch of girlfriends. We had a small party room in the back and they had claimed it for the night.
“An hour later, a group of people come in, including a man in a military uniform. The man asks around for the woman and a friend of hers says she’s in the bathroom. He asks me where the men’s room is and I see the main bathroom was occupied so I pointed him down the hallway to the bathroom most people don’t use because it’s kind of hidden behind the party room. He thanks me and proceeds to the men’s room.
“Next thing I see is the woman running out of the bar and the military man bawling his eyes out. After the longest 5 minutes of my life they all leave, and a friend says she’ll come back for the tab later that night. When she comes back to pay the bill, she tells me the woman didn’t know her husband was coming back from Afghanistan and they wanted to surprise her. Since she’d been going to my bar a lot they thought it would be a great place to surprise her. But apparently, she’d been having sex with all the regulars in the hallway bathroom for months. Her husband walked in on the action.”
This poor guy didn’t deserve this.
21. Mixed Feelings
“This lady came in for lunch and let me know she was waiting for someone. When her lunch date got there I took his drink order, grabbed his coke, and brought it to the table. As I’m placing it down I see a positive pregnancy test in a Ziploc on the table in front of the dude. Her excited face, his shocked, semi-disgusted but trying to look happy face, my what the actual fuck face. Awkward level went up 100%. I murmured something about congratulations and left the table as fast as I could.”
That’s one way to tell him.
22. Cheap Date
“Not worst date, but worst guy on a date. He tried to skip out on the check. I chased him outside and politely asked him and his date to go back in the restaurant, so we can solve the ‘missing money’ case. After a fair amount of back and forth and a bunch of bullshit excuses he pulls the bill and the cash out of his pocket, stuffs it into my hand and said, ‘just take it, man.’ At the culmination of this douchebaggery, his date’s eyes were as wide as the dinner plates they just ate from.”
That’s what he gets for being a cheapskate.
23. What A Jerk
“One Summer, I worked at Cheddar’s. A couple in probably their late 40s walked in and sat at one of the high top tables in the bar area. The man ordered a shot of whiskey and a beer, the woman a diet coke. When the drinks come he takes the shot, takes a pull on his beer, and backhands [her] SO so hard she fell out of her chair. He just sat there calmly drinking his beer until his arresting officer arrived.
‘Edit: For those who asked the woman stood up after a few seconds by which point the manager was walking over. She started walking towards said manager who escorted her out of the dining room (not sure to where and it wasn’t my table, I would guess the office in the back) until the police arrived. The rest of the staff just kind of ignored it and tried to keep working. My section was next to where they were so it was painfully awkward trying to keep working around it. Poor lady.”
Let’s all hope this guy is still in jail.
24. Gotta Share
“I was only bussing tables at the time but overheard an awkward situation for my coworker who was serving them. It was definitely a couple. Definitely a date. And the woman is not into it. Not sure why cause the guy seemed nice enough, but whatever. She’s just not feeling. She was, however enjoying her server, David. To be fair, Dave was gorgeous and sweet and funny and all the girls at work said he was sploosh worthy. This woman agreed. I’m cleaning the table right by them when Dave asked if they wanted dessert.
“The woman reached over, took Dave’s wrist, and purred ‘If you’ll share it with me. You bite mine and I’ll bite yours.’ Right in front of her date. Dave awkwardly laughed, I nearly lost my shit, and the poor date just sat there. Later, I went to clean the table, I saw she left Dave her phone number. Laughing, I gave it to him. He threw it out.”
David could have missed out on a great girl.
Source: The Super Family Biz
25. Nice Tip
“We have a guy that comes in with a hooker (always a very young-looking Asian girl) every other Wednesday for lunch and then his wife and him come in Friday night. He is always in my section and tips me very well for my silence.”
Sometimes, the best action is no action.
Source: Angry Jiggly Puff
26. What A Great Date
“One time a couple came in, she was on her phone from the first moment. At first, he tried to talk to her, but after about five minutes, he just joined her. Just staring at his phone. Her staring at her phone.”
It’s sad that this is how dates go now.
Source: Jelly Berry
27. So Annoying
“I worked at a pretty nice Turkish restaurant and so a lot of the dishes came in elaborate sauces with vegetable garnishes, etc. An older woman and her husband would come in every month or so, and the woman would demand that everything in her meal had to be separate- the orange zest, olive oil, sauce, salt, everything. This took a while (most meals were prepared during the day), and so they were always the last people in the restaurant with the husband looking incredibly aggravated as his wife slowly ate all nine parts of what once had been a roasted duck with couscous.”
She is probably fun at parties.
28. Not Ready
“Had a young gay couple come into the restaurant I worked at about 10 years ago. They were adorable, but about 5 minutes in I think they recognized someone else in the restaurant and the date suddenly became not a date. I guess they were both still in the closet at the time. The rest of their dinner was insanely awkward, never making eye contact and they barely spoke the entire time. Felt really bad for them.”
Maybe this motivated them to come out.
29. No Respect
“Couple sits down at my table. Do the usual greeting. Ask them if they would like to start out with a beverage. The female replies, ‘Coke, please.’ The male stops her, interrupting ‘Uh, make that a diet coke. I’ll take a Jack and Coke.’ The date didn’t get any better.”
This girl should have been smart enough to leave after that.
30. Thanks, But No Thanks
“I was probably about 24 waiting in a 4-star restaurant in Cary, NC, when a young couple comes in and is seated in my section. As I wait on them the female is quite obviously making moves on me and flirting like there is no tomorrow in front of this guy. I am friendly and joking but never let on that I think she is really, really hot. They try to make it clear that they are just friends, so I turn on the charm a bit. That is when the guy asks where the bathroom was. I point and give directions, but he wants to be shown. After we are about 20 paces from the table he informs me that they both would like for me to come home with them.
“Uh, twice the amount of people I wanted to have sex with from this table and politely decline. He goes to the bathroom and when I come back from the kitchen they were gone. $100 tip was on the table and it was an interesting experience over all, just not my cup of tea. She was mega hot, a real bombshell.”
It was a nice gesture, though.
31. Whatever Works
“Working at a pub, a girl came in by herself. A few minutes later, a guy came in. They were clearly on a blind date. They order drinks, dinner, more drinks. The girl started getting tipsy. All seemed well. The pub I worked in had multiple rooms. The guy went to the ‘bathroom’ and came to find me. He bribed me with $20, plus 20% on the bill to say that we were ‘out of beer and couldn’t serve him anymore.’ He said he was having a horrible time and HAD to leave RIGHT THEN. It was extremely awkward, but I wasn’t going to make up a better excuse than ‘we’re out of beer.’”
It’s a good excuse.
Source: Tissue Noir
32. Crisis Averted
“This one time a guy came and wanted a table for 2 because his date would be here shortly. He sat down, and I got him a drink and this Asian lady comes up to him all excited and she wasn’t bad looking but she had a lazy eye that was lazier than me on my day off. They start talking and I come back, and she walks off, I ask the guy if I should get her a drink and he nervously said that’s not his date but ex gf. So, I’m thinking ok? And he’s telling me he has to pay for his drink and leave before his date gets here or else it’s gonna get crazy between them. So, his date arrives and he gets up and tells her some excuse that they have to go.”
Well, at least he pulled it off.
33. Not What She Meant
“This young couple came in, the boyfriend was all smilie and friendly, and the girl was giving me the stink eye. She proceeded to write ‘MINE’ on his forearm with a thick black permanent marker while I was standing there waiting to take his order. I told a coworker about it and apparently, she knew him. He was at her party the night before. She took their food out to their table.
“’Hey! You weren’t you at my house last night?’
“Immediately girlfriend went bat shit crazy screaming ‘you were where?!?!’
“They sat at different tables for the rest of their meal.”
She seems like a sweet girl.
34. Ruined It
“I worked at a really fancy/fine-dining restaurant in Perth. One night a couple came in for dinner and as soon as they sat down the woman said, ‘After I told all my colleagues where you were taking me for dinner that all said that you are going to propose to me tonight.’ This happened as I was at the table pouring them water. It got very awkward very fast as the man didn’t say a word…. There was no proposal that night.”
She should have just kept her mouth shut.
Source: Golden Skit
35. What A Charmer
“My college buddy was working at McD’s when a couple walked in. The guy ordered whatever and when the girl ordered ‘just a coke,’ he told her that ‘wouldn’t work with (his) coupon.’ He just looked at her for a few seconds and she walked out. Dude says to my buddy, ‘Don’t meet chicks online. This was my first time, and it will be my last. I’m not taking some bitch I just met to Fucking TGI Fridays.’”
You only take the serious dates to TGI Fridays.
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Source: Money Wise