Waitresses, What's The Most Awkward Date You've Served? r/AskReddit Reddit Stories | Top Posts

waiters and waitresses have read it what is the most awkward couple date you have ever witnessed at work i work at a dinner theater 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 oh so he brought his own music and everything we are 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't think of to say on mick as 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 there was a couple sitting at the bar together seemed like it was a first date maybe after 30 minutes 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 flammoxed the girl sat at the bar alone for at least another 45 minutes before she left i've told this one here before i worked in a resort hotel high end i waited tables in the fine dining restaurant it was pretty common for people to propose there so much so that i had a system for the whole thing one guy came in and wanted to do the ring in the champagne thing and i talked him into doing a dessert alternative that doesn't result in a sticky ring and champagne on the floor anyway long story short i bring the ring he says damn it i've told you before i'm not marrying you he flips she's super calm about it and basically treats him like a child having a tantrum which to his credit he was not screaming or anything just very upset he left she ate the ducking dessert eventually he came back and paid and they left together super awkward 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 a guy paid but i do not envy that ride home i don't really know if this counts because i think they were married at a table with two crying children how are you doing tonight what can i get you started with to drink father do you have a shotgun back there so i can blow my head off the wife's glare at him was the scariest thing i've ever seen i honestly hope that man is still living edit holy it bless you for the gold kind stranger i was eating at a restaurant and heard the hostess ask a couple she was seating if they were out for anything special the husband replied no it's just our anniversary it has inspired my father-in-law to drop that line almost anytime he goes out to eat now they sat down and from the girl's body language you could tell she was into him as the day 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 ahas in response even perked up a few times to contribute but his monologue never stopped a guy proposed to his girlfriend at the booth across and my friends and me at olive garden when he got down on one knee and opened the box she was shaking her head and then just stared silently it must have been a whole 30 seconds of pure silence but it felt like an eternity then the guy proceeded to describe the ring how much it cost the different aspects of it etc finally the girl just went new and the guy just sat back down and they tried to finish their dinner i caught eyes with our server and he made the most perfect holy hell that was bad face geez that was awkward edit i still picture him saying my love for you is like these breadsticks and limited less than three he didn't say it but i still picture it edit too i really don't think she rejected him because of the location obviously i can't be certain but she seemed like a nice girl and had this what are you doing you hardly even know me expression on her face 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 idk if this counts but when i was a waitress at olive garden one of my tables was going over their divorce paperwork when i greeted the table i asked how everyone was in the woman said terrible we are getting a divorce like wtf do i say to that i guess a husband and wife is a date from the last time a similar question was asked it's been more like 13 or 14 years now more than i waited tables at the olive garden 10 years ago not really ducked up as much as it was funny a guy and his wife sat down at a table and immediately started arguing something about his affair and how a baby from it was costing them money finally it culminated as i was bringing out their salad as i walked away i heard the wife say more than more than well maybe if you hadn't boned our son's girlfriend and gotten her pregnant we could afford to eat somewhere nicer than the ducking olive garden oh look the highlight of my meals unlimited ducking bagged salad maybe you could save up and we could go to joe's crab shack for our anniversary [ __ ] did holy crap this comment has always been my two top rated comments now top three but i didn't expect 16k well hope you enjoyed the show as much as i did at the time 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 twenties 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 are doing well really little guy maybe five foot four 120 pounds comes in with a gigantic woman probably six feet tall and easily 300 pounds both tatted the duck 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 bartender at the time not a waiter but they were re in front of the bar attractive woman comes in with a very loud dude who never took off his rollerblades humbler brags badly mostly just bragged he clearly thought sounded humble loud enough for me to hear in a bar for about an hour thanks her and leaves he thought it was a date apparently she was doing sociological research on people who used tinder i was relieved not technically a waiter but i worked at mcdonald's one of the thankfully less trashy ones and a couple came in woman sat down and the man tried to order there was lots of humming and i hang out what he wanted to buy he ordered two meals that we gave to him and he went and sat down what followed was a 10-minute shouting match about how he wouldn't take her on a rossiproper date and how he ducked up even a mcdonald's date guess he ordered the wrong thing 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 [ __ ] 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 edit just to clarify this was a real rejection not only had they not even finished their meal when he proposed a hostess at the restaurant knew the guy personally apparently it took him a really long time to get over it this wasn't so much as a quid 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 three-month anniversary i'm so glad they found each other not exactly a date but i served a couple one time who had met up to discuss the terms of their divorce at the fancy-ish restaurant i worked at at the time they came before the dinner rush so they were pretty much my only table and every time i check in on them the wife was extremely angry tearful and they were bickering about holiday schedules for their daughter timeshares etc it wasn't the end of the world but it was extremely awkward to butt in to change out their forks or refill drinks while they were so emotionally charged bartending a day shift at an upscale italian place in a high-end shopping center over the christmas season couple comes in starts drinking and is very flirty with each other they clearly like the attention i wasn't quite sure why the man seemed familiar but he had a face i knew from somewhere midway through their lunch the woman used his name and it dawned on me that the man was the husband of my previous boss i told him he looked familiar and asked if he was mark from that restaurant on the way to the beach he said that he was not but the woman he was with insistent on making it awkward and peppered me with questions like i've heard the owner of that place is crazy did you know her she was backhandedly trash trash-talking mark's wife and the whole thing was so uncomfortable he was an all-around bad dude though and deserved it for additional context his family had owned that restaurant on the way to the beach and his wife my former boss ran the place until she caught him cheating they divorced she got the restaurant and continued to run it with her sister fast forward a few years and the two eventually remarry it was during their second marriage that he turned up at my bar with his mistress one of my first jobs in new york was managing a lounge cocktail bar in a high-end hotel at around three or four 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 8 p.m i explained to him that i can't guarantee at etc 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 bar are you by any chance you must be at which point he had this douchey 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 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 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 ordered 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 10 minutes he hung out well after she left we the bar and weight staff invited him to hang out with us at a bar after work ended up being a cool guy 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 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 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 a phone and frantically calls someone and begs for pick up a sap the gist of the call was the guy was her mother's co-worker and her mother had set the date up and our girl really wasn't feeling it about 15 minutes later a guy around her age comes in throws some cash on the table and excuses them she cites some vague emergency end is escorted out the elder 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 an exact change without tipping and leaves 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 looked me in the eyes following the couple started shouting and then both went into the washroom we thought they were smashing and dashing without pain but they came back i heard some of their convo and it was so awkward guy so do you golf cuz i golf girl no and it went on like that for their whole date edit her thanks for the pms so i'm not 100 certain but one time i think someone went to the chain i worked to meet their mail order brides it could have been prostitutes looking back on it but i thought this at the time it was two guys in suits that came in seeming really nervous one comes up to me and lets me know what the girl looks like in case she's confused when she comes in i'd never gotten a heads up like this before andy seemed super nervous sketched out so the women come in and they don't speak very good english and have heavy accents which stood out in the small neighborhood they were dressed very minimally for it being cold and raining outside i point them out to the table with the two men and they're introducing themselves like it's the first time they met with awkward hugs and asking about their flights i got to overhear some of the stilted conversation and talk of money while passing by the other time was when an ex of mine came in with his girlfriend and she left crying for some reason halfway through apparently he brought up that we dated and he kept looking at me which somehow caused that whole scene my ex gf with my friend he didn't know i worked there but she did edit sorry because a few people asked we were dating at the time i was young 15 and she as well 16 i think she wanted to break up with me didn't know how to do it so did it this it was hurtful and obviously i was very sad and angry at the time but i don't hold any oval towards her today i think maturing is a tough path my friend at the time knew we had been dating but he was the sort of friend i see twice a week in class and apparently she told him we had broken up i don't know kids do silly things not a waiters but i was sitting close to them the guy was on one knee and holding a small black box when she opened the box he ran away there was a small paper inside after reading it she started to cry turns out he break with her it was funny sad at same time eastern european couple walks in she looked like she had been crying but they ordered and seemed nice enough a few minutes later i heard a commotion going on in my section i got there in time to see this man reach over and slap the woman hard enough that the whole lounge heard the sound he looked like he was gearing up to hit her again so i instinctively stepped in i was and emma small petite woman with no martial arts training or anything and told him to back off and leave or the cops would be waking him out surprisingly he just left without a fight what was disturbing is that the woman very quickly composed herself and by the time i went over to check on her seconds later she was brushing it off like it was an everyday event i guess it was for her i told her i would feel better if she stayed in the lounge for a bit so we could be sure the man was gone she agreed and i got her a few drinks on the house once she was a little more open up from the drinks she told me her story about how this man brought her to the u.s and that she was afraid if she left him she would end up being forced to go back home she also warned me never to date an eastern european man and that most of them were like that i wanted to take her to the police or to a women's shelter but she refused and wandered out into the night i never saw her again but i hope she is okay and away from that man 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 server 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 couple's table and all i hear from the new server is you ducking it i knew you were cheating on emmy turns out the guy was her bf on a date with his side chick and he didn't know she just got her job there she didn't get fired for what she said 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 when i was bartending this guy came into the bar on a weeknight 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 three years and they had met on tinder he arrived 20 minutes before her expected arrival to get rid of some of his nerves dart 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 double quote she looks at him and says are you joe the guy replies yes and gets up to properly greet her looking incredibly excited dad 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 or average joe husband and wife fight wife cried husband got up and threw a pizza slice at her face not a waiter but i was working as a supervisor in a restaurant and there was a drama lasted for a couple of months there was a couple that came to lunch every day and every day they went to toilet together for like 20 30 minutes so you can guess they had six it was inappropriate but we could nothing with that but one day she came to the restaurant with another man and he was a husband and that was a pretty awkward moment so she started to come to the restaurant with her husband in weekends but one day as usually she came to us with her lover they were arguing and as i've understood they broke up she was crying and so on after that fight i've never seen any of them 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 tasted 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 okay and gave me a side glance over her shoulder that i knew meant i better get a good tip for this the couple clasped each other's hands closed their eyes and made sucking sounds for a solid minute before leaning back in the seats and saying as if they had just had a turkey dinner the waitress was indeed tipped well for her delicious energy and a bartender and seen a bad date go down the girl seemed familiar to me and she kept glancing over at me every now and again then the guy started looking over at me too even when she was up ordering drinks she was glancing at me and my co-worker noticed turned out she was a friend from years ago who just ghosted our friend group the couple had no chemistry at all either there was little conversation and at a few points both were on their phones at the same time eventually the guy leaves and the girls left there alone for 20 minutes so she pulls out her laptop and works on photoshop for a good half hour before leaving 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 in law school i always worked the sunday morning shift at the restaurant in town and it was always sue dead but i'd bring homework so it was mostly okay every other week this couple would come in and order gantes and nachos and sit four hours talking about how attracted they were to each other their sixth life and would joke about sneaking around and whatnot i never thought much of it until one day i walked into the dining room from the kitchen and saw the lady had already been seated in a booth facing me her dude's bald head was across from her facing away from me i approached the table about to ask the love birds if they wanted their usual when the dude turned around and it was a different dude the lady looked at me sheepishly as he mentioned to me it was his wife's birthday and they had never been at my restaurant before lameo well i've commented on this before but basically he was waiting for his girlfriend and he noticed his wife's best friend come into the restaurant so that was awkward for him edit meh he frantically texted the gf she knew he was married when she showed up she sat a few seats down and they talked without looking at each other till the friend left honestly it was kinda ant climactic he even went over and said hi to the friend dates 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 chiming in late but one comes to mind i had a mid-40s man with a young and attractive mid-twenties woman sitting at the bar they were engaging in small talk and ordering drinks nothing out of the ordinary after possibly 45 minutes 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 [ __ ] 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 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 once had a blind date while i was working at an upscale italian restaurant the lady came in early younger and a little on the heavy side to put it nicely she ordered a mixed drink and almost chugged it she drank it so fast about 20 minutes goes by and i'm worried she is going to be stood up finally a guy comes rolling in in a very quick manner like he knew he was late he is tall and fit and doesn't look like he has trouble finding dates i'm a little worried that he won't find the nice young lady suitable but boy how i was wrong and a ducking dumbest for think these things they hit it off talking and laughing all night they pretty much close the place but weren't being rude and staying too late after we closed they eventually work their way out the door and here comes the kicker i go to take some trash outside to the can and they are sucking each other's faces like there is no tomorrow in the lot propped up on one of their cars i go inside to share the news with the staff that the date was a success they were feeling the same way i was about the whole thing we are all excited too figured they went home and shagged it out anyway about 30 minutes goes by and me and the wait staff are leaving through the back door and what do we see the ducking car they were kissing that is now fogged the hell up and bouncing up and down in our parking lot it was the funniest way this night could have ended moral of the story don't put judgments on people's looks and always try to shag on the first date you

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Id: uvd3YWJlJNE

Length: 29min 15sec (1755 seconds)

Published: Thu Mar 11 2021