Awkward dates happen to everyone. But it's interesting to be a third party observer, and even more interesting to be in charge of the table upon which the awkward date is happening. And some stories transcend awkward.
Here were some of those stories.
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.
A Charade For Safety's Sake
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. She proceeds to order them both hard alcohol 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 mans 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.
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 F*CKING 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.
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, "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.
A Good Tip Can Rectify Most Things
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.
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?
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.
The Most Despicable Kind Of Man
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.
I Made BankGiphy
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 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 douchy 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.
A Rock And A Hard Place
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'd 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.
The Cringe-y-est Place On Earth
Not something I saw, but a co-worker of mine saw.
I work at a very prominent theme park. You've all heard of it. There's one restaurant that is arguably the most difficult reservation to book on property. People literally call six months in advance to book it.
While dining in this restaurant, a middle aged man stood up, and requested the attention of everyone in the establishment. He then told everyone about how much he loves his wife and family, who are seated beside him.
Then, he announces to the entire restaurant that he is aware his wife has been having an affair, and he is leaving her. Gets up and walks out on his wife and kids.
I work at a Red Lobster. One time I was serving a table of two who had clearly met up for a first or second date. Both of them seemed very wealthy, but the gentlemen specifically seemed a little odd.
...long story short, the gentlemen began coughing and went to the restroom for a second to get himself together, but ended up taking around 30 minutes. The lady requested we go in and look for him, so we did. Turns out he had a massive heart attack and we found him dead on the bathroom floor. We didn't quite know how to tell the lady, or even what to do really (besides call the police), but by the time we went to look for her she had taken all of his things and she had left. Not so much awkward as much as just a weird, f*cked up scenario...
Just last night, I was ordering for my SO because she asked me to since she's never had a burrito before, I got her a small and me a regular. She had to talk through me because she can't understand the local Yorkshire accent, which honestly took me a good year when I first came here. When we paid at the end we needed her ID for the student rate, but when we left the house she'd asked me to carry her purse since it's been falling out her pocket. The server was giving me dirty looks and confirming with my gf for every item, which confused her since she'd already said she was having the same as me.
I explained to her it looks like I am an absolute ogre and the ultimate controlling boyfriend, which she thought was absolutely hilarious. We were laughing about it all night.
I Am The Cause
I had a couple with a 1y/o skip out on a $30 bill after being very pleasant all lunch. I worked at a restaurant that punished you for walk-outs, so I ate the cost of their dinner out of my own tips.
They came in maybe two weeks later, and got sat with me, again. They immediately recognized who I was, and I greeted them with a big "welcome back". I stood next to them almost all dinner. Like, right next to them, over their shoulder, glaring. Lucky for me, it was a slow night.
So they had a pretty awkward date, yeah.
Nobody Deserves To Be Stood UpGiphy
So this was a few years ago when I was still in college. I tended bar for some time, and we had this one girl come in and sit down. She ordered a drink and we talked to her and apparently she was waiting on her date to arrive.
Now, it's important to know that it was a very casual place and she was very much so dressed up. She was also......strange. Well, one drink later her date hasn't showed up. Two drinks later same thing. Three drinks later she just goes ahead and orders food. By the time she finished her 4th drink it's obvious that she is getting stood up and is starting to get drunk to cover her problems.
It's worth noting that we did end up trying to keep her spirits up, but she finished her night off with a double long Island iced tea. Don't know what's in that drink? Vodka, rum, gin and tequila......with mixers of course.
She was officially toast at this point and fell asleep at our bar. At one point she stumbled to the bathroom and puked and came back to sleep at the bar.
To be fair, it's our fault that we over served her. But man, it was a hot awkward mess the whole time she kept saying how he must be running behind or something. Slowly watching her get more and more depressed with every drink waiting for him.
I hope she found a good person to be with.
Irrational Yet Real
I had a young (early 20s) couple come in on what had to have been a first date. You could tell the guy was into her because of the level of eye contact and focus he was putting into listening to her.
So I'm wiping down the table next to them, and she asks him, "have you done anything fun this summer?"
He says, "yeah I just got back from a cruise"
She responds, "Oh I could never go on a cruise I'm too afraid of pirates."
I glance at her to see if maybe it was a joke, but she's dead serious. He's got a confused look on his face but eventually says, "oh yeah I get that."