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17 waiters and bartenders share the story of the most awkward date they've served.

17 waiters and bartenders share the story of the most awkward date they've served.


Dating is often a chaotic journey of ghosting, flaking on plans, witty banter over texts and wondering if there's any chemistry at all between you and the person across the table at this coffee shop...

The only thing more awkward than being on a bad date, though, is when your job requires you to watch it all unfold with a flake-smile plastered on your face. So, when a Reddit user asked people who work in the service industry, 'what is the most awkward date you’ve ever witnessed on the job?' people were ready to share the most uncomforable romantic flops they've ever had to watch. Nothing gets sparks flying quite like interrupting a 'it's not you, it's me' speech with 'any dessert?'


It was clearly an internet date and the guy showed up first looking excited. 20 minutes later a kind of busted looking woman came in and sat down with him. They were my only table at the time so I was paying pretty close attention to them. They each order a drink and before he's halfway through his, she orders another. And another. And another. He's looking at me kind of desperately at this point but there's not too much I can do except keep a close eye on her behavior.

She starts crying after the 4th drink and tells us BOTH (!!) that she just got dumped last night. Both the dude's and my eyes are wide and I excuse myself politely. They eat, sort of, and she orders two more drinks. He asks for the check at the end and I bring separate ones. He tips 100% and gives me his number. She pays in exact change. - orheavenfaced


I worked at a Ruth's Chris and had this couple come in and sit at a private booth in the corner. The guy was in his late 40s/ early 50s and dressed pretty flashy and the girl was in her early 30s and pretty attractive and put together. He bought her something from Tiffany's and she thanked him, put it back in the box, put the box back in the bag and placed it beside her in the booth (rather than wearing it). She ordered steak and lobster and had probably 4 bites.

The guy ordered tons of drinks and asked me what kind of shots we had (?). He was really trying to create a fun party atmosphere and she was pretty straight faced (playing the superior card). At the end of the night he invited me to come join them 'for a drink' in their room at a very upscale hotel nearby.

I declined (after he paid of course). They left and some time later he came back in because she had forgotten her Tiffany's bag (wtf). Anyways next morning I was out for brunch at a pub and saw the chick in a velour jumpsuit laughing and talking jovially with another guy. - 4shleyhat


I worked at a Starbucks through university, so I saw my fair share of dates. The most memorable one involved this girl in maybe her early 20s. She came in first, dressed up in this nice little black dress, and sat at the 2 person table near the front till where I was posted. This girl was probably 5'2' or so, and 120 lbs give or take.

Maybe 5 minutes later this guy comes in, wearing what looked like normal street clothes. He came over to the table and the girl stood up, and I shit you not, the FIRST WORDS OUT OF HIS MOUTH were 'Wow, you're skinnier in person.'

I've never felt so embarrassed for a complete stranger in my life. And yes, the following date looked as awkward as you'd expect following this. The guy basically talked about himself for maybe 30 minutes, with the occasional 'Uh-huh' from his date, and then the girl left. - Wishmaster57


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 trainwreck 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 the 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. - apexgameplay


So this guy came in with a girl clearly for a first date. After I brought them their drinks I asked if they were ready to order. The man says 'she'll have..'(insert food here, I forget what he tried to order for her). She replied with, 'Actually I'll have this', and gave him a look like f*ck you I order for myself.

After putting their order in I decided to be a little nosey and pay more attention to that table. I listened to the man speak an entire doctorate thesis about himself and the poor girl only got in maybe a sentence. After they eat and didn't want dessert, I asked if they would like the check.

Mr. Ego asks for one check, the lady then interrupts him and says, 'No, we are leaving the same way we came in, separate'. He pays and leaves no tip, she leaves 20% then comes back in to ask how much he tipped and left me another 20% for what he would have tipped for his bill. Most awkward experience to date. - [deleted]


She was so excited. So was he. A meeting set up perfectly by a mutual friend. All was well. Until the end of the night when he paid for dinner: she saw the name on the card and realized she was on a date with the wrong guy. - honeydew_bunny


The scene is set cue valentines day. Up market restaurant. We do these amazing seafood platters for 2. The gentleman arrives first and asks for the platter to come out as he wants to surprise his date. As the ladies arrive we give them a single long stem red rose.

The date arrives at the table sees the platter and starts to go ballistic. 'I'm f'ing allergic to seafood do you want me to die'? Hits him over the head with rose then flings it at him. He looks bewildered for about 5 seconds looks around the packed restaurant shugs and then tucks into the platter. - Isthisaclue


This wasn't a 'date,' but I worked at a bar that was a notorious pick up joint. This guy was sitting at the bar and I noticed him take off his wedding ring as soon as he came in and sat down. He started talking up this woman, it was getting near closing time, and they were getting ready to leave, together. I asked one of the male bartenders to borrow his wedding ring for a minute.

As the guy and the girl were getting up, I put the ring on the bar and said 'Is this your wedding ring? I think you may have dropped it on your way to the bathroom.' He turned beet red and she ended up leaving without him. She did thank me though. - DTownForever


I had a regular come in on a date and he is usually a laidback and chill guy but I guess he was nervous or something because he came in as high as a kite. He kept telling the girl how beautiful she is and kept repeating happy and lucky he was. I guess the girl couldn’t handle it anymore because she just booked it before food came out.

Then my regular started rampaging through the restaurant and stomping the floor really loudly and he tried to go into the kitchen and my coworker tried to stop him. He got pretty hostile and tried to fight my coworker but I stepped in and told him that customers weren’t allowed in the kitchen and he went from 100 to 0 but went back to stomping around the front of the restaurant.

My boss came out to see what the commotion was and ended up telling the guy to leave. He tried to fight my boss but he left after my boss threatened to call the police. I never saw that guy come in again after that incident. - ihazpie


It wasn’t my table but it was still awkward to be around. This guy comes in, orders a drink, and starts talking to the server about how he’s meeting his ex. They had just broken up a few days beforehand but he was pretty sure she was gonna get back together with him. Super excited.

She didn’t show up for an hour, maybe longer, and told him they weren’t getting back together when she showed up. She stayed for an appetizer but apparently it was a horrific silence before she got up and left. - st_bart


Related but also not break up with someone at wagamamas!! The tables are communal bench setups and i felt way too involved into this couple’s argument considering all I wanted to do was enjoy my ramen :( - bpdqween


I had a guy, at the end of the meal... after drinks, appetizers, the best entrees in the menu, a luscious chocolate mousse cake, and champagne... this guy says to me when I ask if there will be anything else... “What can I do to guarantee I’ll get laid tonight?” His date turned beet red and gap jawed. I said, “I think you were pretty much well on your way... until you said that.” His date just said, “Yup.” - akoontz


Not a date, but an event to announce a divorce. Dude came with his wife, little late for their reservation. No problem, it wasn't busy. So i sit them down, offer some drinks etc, they order a bottle of the most expensive Champagne we have. Wow okay...

Well as the time goes, food starts to come out for them, as i walk to the table, the dude with a straight face tells his wife: 'I'm leaving you. I've contacted a lawyer, he should speak to you soon.' She was shocked, but kept it together while I awkwardly put the food on the table. As soon as I left, she stood up and went towards the barhrooms. Dude called me over, he paid the bill, got up and left. - iamnotexactlywhite


This guy came in and ordered a water while he was waiting for someone, he seemed pretty nervous. Soon a girl comes and joins him, they seem familiar with each other. They eat dinner and order some dessert. I come back to check on them and she looks like she's about to cry, so I turn and go to another booth.

I give it a few minutes and when I come back she's gone and he has his head in his hands, dessert basically untouched. I felt SO bad having to give him his check. He just kind of smiled at me and I didn't know what to say so I told him 'I can put that it a to-go box if you're looking to leave. But you can stay here as long as you need to.' He just nodded. I brought him a box and he left about 5 minutes later. - PeachRing23


I worked at a pizza place in the mid 90s with old school red booths and a sitdown Pac Man game. A young couple in their late teens came in and sat down. It was already after 8pm and they had apparently gone to a movie earlier as they were talking quite loudly about (I know, wow, right?)

They order a supreme pan pizza (pepperoni, beef, pork, green pepper, onions). I ask if they want everything on the pizza and they both say yes. Less than 15 minutes later I bring it out and serve the first slice to her then a slice to him. Ask if everything is good and walk off to get some more drinks for them.

I hear a yell 'why does this pizza have onions on it?!!!?' from across the dining room. Of course everyone stops to look, including me. This kid is standing on the booth, yelling at me. Immediately I walk back with their refilled cups to see what the problem was.

I get back to them and he immediately goes into a tirade about onions throughout the pizza. I apologize for the onions and offer to get a new one made. Instead he starts yelling about the green peppers and how they are super spicy (yes, bell pepper is spicy according to this guy) and I was just trying to make his night horrible. I look over at her and she has her face in her hands.

I rush to get a new pizza made for them, this time I confirm every item on the pizza and get it comped by my manager who was sitting in the back laughing at the absurdity. She finally goes out there to talk to them and this guy tells at her. I look their way and the girl is with her face in her hands again.

The new pizza comes out and my manager and I both walk it out and again, I serve the first slice. He immediately goes off that the pizza is too hot and will cause injuries. My manager tells me to go away while she handles it. This time the girl gets up and walks towards the restroom. She stops me and apologizes for his behavior, that it was their first date and he bought a lot of stuff at the theater.

I immediately understand what he is doing, he doesn't have any money so he is trying to get free food for his date. It worked. My manager has gotten him to stop yelling and the young couple has started eating. They finish and get up to leave. She starts yelling at him for not tipping. He says I didn't deserve a tip after messing up so much. She calls him out for being a cheapskate and tosses some money on the table and walks off. He picks up the money and pockets it.

Out in the parking lot she starts yelling at him again. She walks in and asks if I got my tip, of course I answer no and she storms out again. Yelling at him for stealing. She walks back in dragging him behind her by the hand and forces him to give me the tip and apologize. I don't think there was a second date. - Nautiwow


I was a bartender for a TGI Fridays. One night there was a couple on a date, they seemed really familiar with each other and nothing was really out of the ordinary- until the lady's husband walks into the bar. He. Went. Off. He yelled at her about how he was at home with the kids while she was on a date, how they'd been married for years, and calling her all sorts of names. If I remember correctly he didn't acknowledge the date, and the date kinda sat their like a lost puppy with his tail between his legs. He (husband) then grabbed her purse and threw it at the door, telling her to get her a*s up out of the restaurant they were going home. They left, and soon after the date closed out and left too. - coochiesneeze


I worked at an upscale seafood restaurant for about a year. One particular woman would bring in a different date each week, and every single time she was there she would erect this barrier between her and the date. I’m talking salt and pepper shakers, menus, dishes, drinks.

Whatever she could get her hands on she would construct a physical barrier out of and then carry on with the date as if things were completely normal. The confusion and distress on the faces of the men she would bring in was always my favorite part of Saturday night. - liv4pool

Sources: Reddit
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