1: Romantic Proposal Gone Wrong.
“I work at a dinner theatre, and we usually do proposals where we set up a ‘random draw’ where the ‘winner’ comes up on the stage to win their prize, and are then surprised by their partner who proposes. It’s usually sweet and makes everybody in the room all fuzzy and warm.
This one guy wanted to take it further and requested to perform a song — he brought his own music and everything. We’re pretty easy going at this job, so we agree to let him do it.
We do the fake draw, the woman comes up on stage in front of a room of 400 people, and the music starts to play.
Apparently, this guy was a little nervous, and he compensated by having a few drinks. So what follows is a slurred performance of a song written by this guy, that seemed to focus on how he was sorry for cheating on this woman with her sister and at the end of it, he gets down on one knee and proposes.
Usually this gets a round of applause, encouraging the person to say yes; but not after that train wreck of a performance. The poor woman was just holding her face the entire time and starts shaking her head and says “No, what’s wrong with you?” She storms off and leaves him and our stage manager on stage to a bunch of murmuring from the audience. The only thing our stage manager can think of to say on mic is “Well, that’s that.”
The guy ended up staying for the rest of the show and had many more drinks. That was years ago and it still remains one of the cringiest things I’ve ever seen.” – AgainstBelief, Reddit User.
The guy didn’t plan his actions right. He should have confessed in private and gotten her forgiveness. If she had stayed after forgiving him, his proposal might have worked.
2: Forced Date.
“They came in and the first thing I notice is that the woman was noticeably older than the man but I don’t really judge about that kind of thing and I also don’t assume people are on dates. Maybe she is his aunt? Or they are just friends?
So, I went to go ask about drinks and do the usual peppy greeting and she is super chatty. Basically, talks for him and answers questions that were straight for him. Okay, I think, maybe that’s just how they are. Whatever.
She proceeds to order them both hard alcohols straight…at 10 am…I figure “eh maybe they are on a vacation together”. You never know.
It finally hit me that something wasn’t right was when she wouldn’t stop making sexual comments about the two (which is how I knew it was kind of a date). I am talking straight up things like “I am 53 but with the amount of work I have had done to my downstairs, he won’t be able to tell tonight if I am actually 23” I am watching the man’s face and he looks pained.
I watch the table from afar. I realize it kind of looks like a date gone wrong, but they seemed to know each other so I am not really sure what is going on (and servers always chat and theorize about their customers in their free-time) when the man gets up and comes over to me and asks me to chat with him around the corner really discretely.
So, I do. He looks as me and is talking super-fast as he explains that this is his boss and he has to meet with her quarterly and she just has to sign a single form to approve what he has been doing and she insists on going out for a meal and drinking and then trying to sleep with him. Every time. I was horrified for him– he looked that panicked.
He said that he usually gets her to sign it before they leave the restaurant and then makes an excuse to ditch her. We made a code sign (him patting the back of his head three times) so that I could intervene when she would get far too inappropriate but honestly, she didn’t change much when I would come. He also asked me to bring him fake alcoholic beverages, said I could charge him for the alcohol but to make them water or just soda.
I still think about him sometimes and wish I had gotten his name or something so I could check in and encourage him to report her, but in all honesty, she probably owned the company he worked for or something the way she spent money and looked like.” – rufusmaru, Reddit User.
Their guts were right the moment the unusual couple walked in. The guy must have been successful and escaped his boss’s snare. It’s either that or the worst-case scenario played out.
3: Quick Turn of Events.
“First date, I would estimate college age. They’re eating and the girl says “I’m having a really nice time, but my friend just texted me and asked me if I wanted to hang out, and I said yes, so I actually have to go.” – youngandstarving, Reddit User.
It’s either she lied about having a nice time and used her friend as cover up. Or she did have a nice time but the event her friend asked her to was better. We never can tell but that must have hurt their date really bad.
4: Weird Couple.
“Couple came into the restaurant dressed very goth. I wasn’t their server but I was running the cash register just a few feet away. They proclaimed to everyone that they were energy vampires, but not to fear them because they won’t hurt us. They said they didn’t need our food for sustenance, but enjoyed the taste.
After ordering the meal they then politely asked the waitress if she would stick around for a second so they could feed off of her aura so they could have enough energy for the night. The waitress said ok and gave me a side glance over her shoulder that I knew meant “I better get a good tip for this”… The couple clasped each other’s hands, closed their eyes, and made sucking sounds for a solid minute before leaning back in the seats and sighing as if they had just had a turkey dinner. The waitress was indeed tipped well for her delicious energy.” – Hexiron, Reddit User.
They were either doing it for fun or were pretty serious. Either way, they got the attention they needed. Their ‘meal’ also got paid for her troubles in the end.
5: Caught Red-handed.
“Late to the party but I will share my story. Had a couple come in one night and everything seemed to be going fine. We just hired a new sever who was training and I asked her if she had any questions.
She was still nervous about greeting tables so I told her she could shadow me and watch what I do. We go over to the couples table and all I hear from the new server is “YOU FUCKING BITCH I KNEW YOU WERE CHEATING ON ME”
Turns out the guy was her bf on a date with his side chick and he didn’t know she just got a job there. She didn’t get fired for what she said.” – CigarJpug, Reddit User.
Their boyfriend must have been patronizing the restaurant or it was his first time there. Whatever it was, he was caught in the act. The manager was kind enough to not fire her for her outburst.
6: Failed Date.
“When I was bartending, this guy came into the bar on a week night, average looking guy, late twenties. He sat down and asked for a drink and told me he was nervous because it was his first date in 3 years and they had met on tinder.
He arrived 20 minutes before her expected arrival to get rid of some of his nerves…two hours passed and he waited for her with no text or call explaining she would be late.
This woman walks in, walks up to the guy and I’m thinking “Wow! She really came! “
She looks at him and says “Are you Joe?”, the guy replies yes and gets up to properly greet her looking incredibly excited…she says “no thanks…” and just leaves.
What a foul creature. Joe (not his real name) and I proceeded to get way too drunk for a Tuesday. Poor average Joe.” – Corticulture, Reddit User.
Joe must have felt way more terrible. She was late, rude and manner-less. However, you’d agree that he’s better off with someone else.
7: Break-up at Proposal.
“I worked at a fondue place. 1.5-2-hour meal for two people. Four courses, the works.
Couple came in and he had pre-arranged with us to present an engagement ring with the chocolate course with melted chocolate on the plate spelling “Will you marry me?” Also roses and other embellishments on the plate.
Apparently, the entire meal she was explaining to him how bad he was at being in a relationship. Too needy, too emotional, somehow also didn’t spend enough time with her and wasn’t connecting with her? It was an hour-long breakup speech.
We come around the corner with candles lit and the chocolate fondue and the engagement ring on the plate, the table next to them did everything they could to wave us off, I was holding a camera to capture the magical moment…which never came.
He tried to get his prepared remarks out, but it was so bad we eventually left the dessert at the table and tried to act like nothing had happened. She left before the check came.” – Jps1023, Reddit User.
For her to think he was terrible being a boyfriend, she wouldn’t agree to marry him. Too bad he was heartbroken after planning his proposal. She would have said no either way.
8: A Little Violence.
“Husband and wife fight. Wife cried. Husband got up and threw a pizza slice at her face.” – Agentx6021, Reddit User.
They must have gotten into a heated argument. It’s either that or the husband was furious over something she did and retaliated. Maybe he’s abusive, we don’t know too.
9: Knocked Out.
“Date seemed going well, but the guy was nervous and fidgety. He was rocking back on his chair a little as he would talk and eventually flew too close to the sun. Toppled his chair backwards and knocked himself out cold. And peed his pants.
He had to be taken out of the dining room on a stretcher over the span of 20 minutes, while his Tinder date did the honorable thing and immediately went to the bar and ordered shots.
We gave them to her on the house.” – ANPhiK, Reddit User.
His nervousness got the best of him. Either it was his first date or he was scared it would turn sour soon. His date was probably too shocked at the turn of events.
10: Divorce After Dinner.
“I guess you could call this a couple date. I was working at a wine bar when a married couple sat down on a pretty slow night. I went over the specials and they ordered.
Once appetizers came out the man thought it would be a good idea to serve his wife divorce papers. I did my best to avoid that side of the bar. I did bring out tissues for the wife who was breaking down. I ended up boxing up the dinner. The guy paid but I do not envy that ride home.” – ThereandBack22, Reddit User.
We think the timing was bad. But what do we know? He probably didn’t think there would be a better time.
11: Silent Fights.
“Served a deaf couple having a fight. They went from both of them signing furiously to her crying and signaling to me for a stack of napkins for, I assumed, her tears.
She whips out a pen and starts writing paragraph after paragraph angrily. It was awkward because I kept having to come back to the table since they ordered multiple courses and he was just eating and signing while she was hunched over the table writing away while crying.
When they finally left, they tipped me pretty well though so I guess it wasn’t too bad?” – midgetT-rex, Reddit User.
It’s either she was trying to explain something or was mad over something. We can’t know for sure. They probably tipped midgetT-rex for her trouble attending to them.
12: Fake Movie Star.
“One of my first jobs in New York was managing a lounge/cocktail bar in a high-end hotel. At around 3 or 4 o clock, a guy that looked pretty cheesy (slicked back hair, bad suit etc.) came up to me and demanded that he get that window table tonight for his date (he had a reservation for 8pm). I explained to him that I can’t guarantee it etc. and he slipped me $400 with the “How about now” look in which I eventually caved in and told him that I’d take care of it.
He then pulled another stack of hundreds and started counting them in front of me while asking if I could go a little extra by coming over to the table when he was there with the date and pretend that I knew him from a movie. At this point, if I’ve gone this far, why not?
Sure enough, he rolled around later in the evening with a blonde bimbo and after they’d had a glass of champagne, I approached the tables around them, checked on how they were doing before going over to him and did the whole “How are you enjoying your evening?”
And before walking off I did an Oscar worthy double take with a “Are… are you… by any chance…? You must be…” at which point he had this douche smile lapping up the “recognition” he was getting from this young dude he’d just paid off. Most importantly for him though, it worked – she was loving it – and they left shortly after and he slipped me another $600 on the way out.” – nmouchel, Reddit User.
They were tipped for the act and felt it was harmless. Either the guy wanted to impress his date and make her think he was a celeb. Or he wanted to get something in return from her.
13: Excited Lady and a Jerk.
“Was a cocktail waitress at a bar in a high-end restaurant a couple years ago. This couple comes in right around peak hours, guy looks annoyed, girl looks really excited. The whole time the girl is trying to talk to this guy and he’s completely ignoring her. He gets a call and talks on the phone for a good 10 minutes, hangs up and starts talking to anyone around him but her.
He’s getting more and more drunk and starts hitting on the female bartender and eventually the cocktail waitresses (myself included) telling us he could get us all much better jobs in Atlanta. The girl he’s on a date with has started crying at this point and once he actually notices he yells at the bartender because it was obviously restaurant’s fault for her being upset.
She yells at him to stop yelling at the bartender because he’s been such an awful date and he goes off, tells her he didn’t even want to eat here, she should’ve picked a better place, and he isn’t paying for her food and drinks.
He then tells her that she didn’t look fat in her picture and he wouldn’t have asked her out if he’d known she was that big (probably met online kind of thing). She retreats to the bathroom and the guy continues to make a scene. Another girl at the bar and I go to check on her while the bartenders and manager try to deal with him. The girl is super upset and I tell her there’s a back door she can leave through and I can get her tab from the bartender. I go back out and the guy had already stormed out and refused to pay, leaving his date with a nearly $200 check. She didn’t have the money to pay so a couple of the bar regulars covered it. Made the whole night super awkward and stressful. Definitely one of the more memorable experiences of that place.” – icysunshine, Reddit User.
The guy’s statement confirms that they met online and he was impressed with what he saw. He was probably more upset at her restaurant choice. He acted like a total jerk to make her know how unhappy he was. Quite insensitive.
14: Unusual Match.
“Really little guy, maybe 5 foot 4, 120 pounds comes in with a gigantic woman, probably 6 feet tall and easily 300 pounds. Both tatted the fuck up with piercings to match.
The woman orders her dish and before I get the guy’s order, he says in a sexy voice, “I think you want more than that.” She smirks at him, says, “You know I do,” and orders three more entrees. This was clearly a thing for them. They seemed incredibly happy together and became regulars at my restaurant.
I feel like I played a not insignificant role in this bizarre couple’s eating fetish for like three years.” – significantmundanity, Reddit User.
They’re happy together and that counts more. They’ve probably discovered what works for both of them and stuck to it. Uneven match but they click, right?
“There was a couple at my work having drinks, girl went to the toilet, came back and admitted that she’d been sleeping with the guy’s brother. Apparently, glasses were thrown across the room and they both got kicked out.” – Foxjessie, Reddit User.
The guy probably confronted her and she denied. She must have felt bad and went to rehearse in the toilet. Too bad, he didn’t take the news lightly.
16: Break in Transmission.
“Chiming in late, but one comes to mind. I had a mid-40’s man with a young and attractive mid 20’s woman sitting at the bar. They were engaging in small talk and ordering drinks, nothing out of the ordinary.
After possibly 45 mins a lady storms into the bar, and immediately goes up to them. She grabs the man by the shoulder and says “You…You’re a cunt” and walks out.
The man turned to his perceived date and says “Yeah, she does that” and then left the room, leaving his date to sit there, staring blankly into oblivion until she left. Odd.” – LSDnoiseparty, Reddit User.
It’s either the lady was his wife or someone who feels offended by his actions. We can’t be too sure. Either way, the date ended with him leaving his date all of a sudden.
17: Two Guys and A Girl.
“A girl brought two tinder dates and played them off each other game show style. They seemed to be unaware this was what would happen. Splitting the bill was hilarious.” – prosperpines, Reddit User.
It’s either the girl was so attractive that none of the guys wanted to give up. Or they were confused as to what’s going on. We’re pretty confused as well.
18: Awkward Situation.
“Was a bartender/waiter a few years back and I was delivering some food to a table to find out that it was my ex and her new boyfriend sitting at the table. We had only stopped seeing each other a month earlier so it was incredibly awkward for everyone.” – CMMND, Reddit User.
Their ex might have done that intentionally since she might have known where he was working earlier. It’s either that or it was a coincidence. A coincidence that might have made the rest of the date pretty uncomfortable.
19: Bad Night.
“I was at one of these fancy speakeasy type bars they’ve started opening up installing a new invoice printer for their Point of Sale system. Waiting for the printer firmware and driver to install can take 30 or 40 minutes on slower computers, so I’m part of the people watching.
As I’m standing there watching bars fill up, I notice a gorgeous blonde in her late 20s is sitting with a very well-manicured looking guy in his mid-40s. He’s dressed like he just left a high dollar law firm, and she looks like she’s going to a fancy professional cocktail party after their date. He is polite, talkative, and super into her, but you can tell that she isn’t reciprocating the feelings. To be honest, by the look on her face, she’s anywhere but in that bar at the moment.
The guy goes to the bathroom and she quickly picks up her phone and frantically calls someone and begs for pickup ASAP. The gist of the call was the guy was her mother’s coworker and her mother had set the date up, and our girl really wasn’t feeling it. About fifteen minutes later, a guy around her age comes in, throws some cash on the table and excuses them. She cites some vague emergency and is escorted out.
The older guy continues drinking ($140 tab, note that I’m standing at their main cash register) and starts flirting with the waitress, fails to get her number, pays in exact change without tipping, and leaves.” – mesoziocera, Reddit User.
The guy wasn’t having a lot of luck with women that night. He must have been really embarrassed and wanted to feel good with the waitress who also turned him down. She should have refused the date from the onset.
20: Naughty Couple.
“This trashy couple I served were disgusting people to begin with and to top it off the woman was trying to be sneaky and jerk him off under the table.
Unfortunately, I saw this happening and just pretended like nothing was happening because I didn’t want to deal with it.” – kklolzzz, Reddit User.
They should have gotten a room. This act of indecency would have disgusted anyone who saw it happen. They probably couldn’t wait till they were alone.
21: She Wanted A Better Ring.
“When I was waitressing in college, I witnessed the single most embarrassing thing to happen to a person to date.
Right in the middle of their dinner (and in the middle of our Friday night dinner rush), this poor guy stands up, taps his wine glass to get everyone’s attention, and then proceeds to tell EVERYONE what a fantastic person his gf is, how much he loves her, and how lucky he is to have her in his life.
The whole time this is happening, she is just sitting there watching him with the most boring look on her face. It was so weird. Kind of like, ‘Yeah, tell me something I don’t know”.
Then poor guy pulls out a ring, gets on one knee and asks her to marry him. She gives him the most disgusted look imaginable and says “THIS is the ring you expect me to say yes to? Are you retarded? Could you be any cheaper?” Then she gets up and walks out, leaving the poor guy just kneeling there.
I didn’t charge him for the meal.” – Penya23, Reddit User.
They were kind enough to not charge him for the meal. The embarrassment was enough. The lady must have been upset about the choice of restaurant too and was clearly materialist.
22: Obvious Cheat.
“Working at a chili’s on Valentine’s Day, the girl gave me her number with her boyfriend in the bathroom, I came back and had to deal with her being sweet to him and nice the rest of the dinner. I did not call or text her, just was weird every time she’d look me in the eyes following.” – PrinceLemonade, Reddit User.
They didn’t call because they feel she would do the same to them. She seemed like a flirt and would go for the next guy. Just the same way she chose him.
23: Something Feels Off.
“I had a middle-aged couple who seemed perfectly nice. The man asked me where he could go to smoke. I pointed him in the right direction and then started heading back to the kitchen which was in the same direction.
He followed me and told me that the woman with him was his ex-wife. Not knowing how to respond, I said it was nice that they got along so well. He told me she just pretended to seem nice and was actually a terrible person.
I was feeling uncomfortable enough, but then he started to ask my age, if I had a boyfriend, what I was doing later. Thankfully, I could excuse myself to the kitchen. However, serving that table was awkward after that especially since she kept touching and complimenting him.” – Rosepetals7, Reddit User.
It’s either the man was a terrible liar and just wanted to flirt. Or he was being truthful and was looking to get a bit of air. Whatever it was, Rosepetals7 didn’t find it less awkward.
24: Matching Outfits.
“This wasn’t so much as awkward but just unusual: Served a young couple at a high-end Italian restaurant that came in wearing matching outfits. I asked them what the occasion was. They were celebrating their 3-month anniversary. I’m so glad they found each other.” – Oreosforever, Reddit User.
They probably do this every month. Their own way of having a good anniversary celebration. Oreosforever probably hasn’t had this kind of experience before.
25: Sad Family Time.
“This wasn’t a romantic couple, but it was a father and his daughter. I thought everything was going fine but I could tell I was intruding in on times that they wanted to be alone, so I tried to adapt and stay out of their way. I don’t know what happened, but suddenly the daughter begins to cry and I had no idea until I approached and asked how everything was.
Immediately he looked annoyed, which was understandable, and I just left and didn’t talk to them for the remainder of their meal– including when I dropped off their food and got them the check. She cried the whole meal and it was a very emotional scene, and I’m not entirely sure what had happened except maybe a divorce or a death in the family.” – BR0JAS, Reddit User.
It was either the father dropped bad news. Or the father said something that hurt his daughter. He was probably annoyed because he didn’t expect an intruder in their family talk.
26: He Kept Talking…
“They sat down and, from the girl’s body language, you could tell she was into him. As the date progressed, she closed off, then sat pretty much sideways, then was playing on her phone. The body language shift occurred over maybe 1.5 hours. He didn’t stop talking the entire time.
She did give some nods and “uh-huhs in response; even perked up a few times to contribute. But his monologue never stopped.” – TheStankTank, Reddit User.
They could tell that she was into him so they were able to judge that the date didn’t go well because she wasn’t. She was probably tired of listening and him not listening. He probably just cared about himself.
27: Strange Silence.
“A woman in her 50s and a guy in his late 20s/30s. He was wearing a graphic, gory Happy Tree Friends shirt and she was in a full fur black coat with a mesh shirt underneath (??).
Straight up gothic Cruella De Vil. They didn’t speak a word to each other except when I came to ask how their meal was going, and they both started complaining that their wine suddenly tasted of soap (even though they’d had the same bottle and glasses since they sat down. Convenient that they start complaining for a free bottle when they’re reaching the end of their old one). Either way they literally just sat staring at each other in silence the whole meal, then paid, got up, and left. Seriously the strangest date I’d ever seen, and the most on-edge I’d ever felt serving customers.” – naesheim_bech, Reddit User.
They must have been mad at each other and decided to have a ‘quiet’ dinner. Or it’s a thing thy love to do. Everyone seems to have what they enjoy doing. We think them complaining meant they’re ‘like-minded’ or something.
28: Awful First Date.
“There was a couple sitting at the bar together – seemed like it was a first date. Maybe after 30min of them being together I’m in the back-rolling silverware and the dude comes running into the back and goes, “there’s an exit back here, right?” and proceeds to bolt out of the back door.
We were all flummoxed. The girl sat at the bar alone for at least another 45 minutes before she left.” – HappyLittleTrees17, Reddit User.
It’s either he was trying to leave unnoticed or actually ran away. He was probably unimpressed or wanted to be as faraway from the lady as possible. There are a lot of possibilities but we’d never know which is right.
29: “Don’t Order for Me.”
“There’s a habit of some older couples where the elderly gentleman will order on behalf of his wife. I guess it might have been cute and romantic once, but it doesn’t work with some younger couples.
I was serving a younger couple (early 20s), who seemed pretty early into the relationship. They were ordering drinks and he orders her drink for her. Far from being dazzled by him knowing what she wanted, she didn’t want any of it.
“Well I’d actually like a latte, not a coke. But fine whatever, if I don’t get a say…”
He responded quite angrily with “oh sorry, have what you want then!”
She got her latte and he glared at me. They ate and left. Not been in since, I’m sure they’re doing well”. – Durnovarian, Reddit User.
It seems the lady doesn’t buy the idea of him ordering for her. Or they had a pretty fight earlier. He should have just let her order.
30: Lies Unfold.
“This was just before Tinder and dating apps were a thing. It was a blind date, guy and girl. Guy shows up first and is excited, until he sees his date. She had their mutual friend show him an old photo of her because she had since gained significant weight. You can tell he was let down, but decided to make the most of it. They order drinks and appetizers.
We didn’t even get appetizers out before the guy noped out of the date. He sat at the bar asking us to bring the appetizers to him there. Her weight wasn’t the only thing he was lied to about. Her personality and his clashed so hard the date didn’t last ten minutes. He hung out well after she left. We (the bar and wait staff) invited him to hang out with us at a bar after work. Ended up being a cool guy.” – wheelchair_boxing, Reddit User.
He was willing to carry on the date despite his initial disappointment. We think he couldn’t handle the personality clash and every other thing. Good enough, they made him enjoy the rest of the evening.