Waiters Shared Stories Of The Worst, Most Awkward And Hilarious First Dates They’ve Ever Seen

by 1 year ago

I tried out waiting tables for a few weeks during a Summer back in college and quickly found out that my life would be much better spent behind a computer screen than having to deal with customers every day. Serving tables was never for me, and I was ultimately forced to quit after a few weeks in when I dislocated my shoulder coming off the high ropes one night during a game of beer pong which left me unable to carry a tray of food or drink (thank god, got me out of there sooner than I’d expected).

This isn’t my an article about my story, though, but I can tell you that story in depth later if you’d like. This article is a collection of stories from servers who have witnessed incredibly awkward/bad/hilarious first dates, so let’s get to reading (via AskReddit):

Man and woman cozy in a booth. Different woman storms in through the front door literally dragging two kids behind her, right past the hostess station to stand defiantly in front of the couple and proceeds to BITCH. Dude was nailed.

I work at a fairly nice Italian restaurant, where we do a lot of business. One night a man who I was not even serving came up to me while I was punching an order in on the computer and hands me $20 and a napkin with a phone number on it.
He proceeds to tell me “I am on the worst date of my life, this woman is horrendous and I have to get out of here. Take this $20 and please go to the nearest phone and call me and tell me that I have to get home right away. I don’t care what excuse you make up, I just gotta get the hell out of here.”
Initially, I thought he was kidding until 2 minutes later the guy who was serving him came up to me to tell me how wicked this woman was and how he could tell the guy didn’t wanna be there. I promptly called that guy as soon as I had a free minute.
One of my shining achievements as a server.

I was a waiter as a first job.
It was an attractive young woman and an average-looking man. First off, these people were 30 and I have no clue why they decided to go to Applebee’s for dinner.
The guy was wearing plaid sleep pants and a oversized red zip-up Columbia. The woman was dressed more nicely, but it was still casual. All goes well until it comes time for entrées. This guy orders a fuck ton of ribs (a few full racks) and refuses the girl her original order of a house sirlion, which was only about $6, less than a fifth of his order. The man orders a four dollar salad and a water for her. The woman stopps talking completely while the man talks about some crazy party he went to. The man guzzles a few Strawberry Quencher Iced teas, says “Seeya Friday, bitch” and leaves her with the bill.
She said the guy seemed nice when they talked on Tinder, but was very uncomfortable with him in real life, and afraid to say something. A co-worker and I paid for her meal, and later she and the same co-worker starting dating, and they are engaged now.

Served a couple a few months ago. Everytime I walked over, he would always be the one talking, and she would just be sitting there not having a good time. At the end I asked if it was one bill or separate and she immediately piped up “SEPERATE”. I go and take his payment, and as I hand over the Debit machine to the girl, I see the guy take his phone out and start swiping through tinder.

It was one of my first dates where the waiter definitely could sense the awkwardness. I was a junior in high school. I had been flirting with a senior for a couple months and asked her out the day I got my license. I picked her up from her house and within 1 minute of being in the car she got a phone call. One of her best friends died of a Brain Aneurysm earlier that day.
I told her that we could delay the date and offered to take her home, but she declined and insisted we carry on. We get to the restaurant and she is crying at the table. I didn’t say any words to her other than “are you okay?” the whole date because she was either texting her group of friends or couldn’t make out words due to being so hysterical.
The waiter kept coming by and sensed how awkward I was feeling. Out of all my restaurant experiences, I have never received my entrée and check so fast. The waiter was a true bro.

This one’s a little long, but it’s my favorite read.

The_Neck 25.1k points 14 hours ago*
Ok so I have been a bartender and a waiter over the years and have witnessed a couple of really sad ones, a couple crazy ones, and one that was just brutal. This one was the best of them all I thought.
Good looking dude, fit, clear shaven, kind of looked like Jim Cantori from the weather channel but younger(24 had to card him) and slimmer. Sitting at the bar going on about how he had a date with this girl that his best friend was crushing on hard. That his friend just refused to ask her out because she was into him instead. He was really getting into his story when she walks in and he clams up like someone shocked him. She was by anyone standards drop damn dead good looking and killing it in a little black dress and high heels. It was really that rip the record kind of moment.
Anyway, she comes up and the do the little kissy huggy greeting and she orders a tequila shot with a lime. He does one with her and they banter about getting that out of the way and move in to a little more intense banter and out of the blue this dude whistles at me. Shocked honestly as the bar is pretty empty. He whistles at me again while I am looking at him trying to figure out if he really just whistled at me like a fucking dog. “yo man, more shots!”.
Disappointed as he really kind of seemed like a nice guy I go to pour him a shot and let him know I am not a dog he does not need to whistle to get a drink. “Sure sure man..no worries just keep and eye out we are gonna get lit! Yo!”.
I retire to the side bar real quick and one of the other guys working that night starts to talk to him while the girl goes to ladies room. When she gets back he whistles at the other bartender again and shouts “Hey man! Where are my shots! Pronto!”. This guys starts just hammering shots. Not crazy but pretty damn quick he is though at least five. Girl only did the one and is sitting there sipping at a Wine.
The dude, we will now call “YO!” starts to get a bit sideways. Nothing big, just loud, laughing at his own jokes, talking over the girl every chance he gets. He then announces that he has to piss on a rock and walks to the back. The girl looks mortified and sad. She is texting away like a mad man. Then I hear him in the back raising some cane and out he comes with a dude under his arm. They sit down and he starts talking to different girl at the bar. He is not really piss drunk but well on his way and says something out loud to the other girl about gay people and walks outside. His friend follows quickly after and the girl is left at the bar alone.
Five minuets later the friend walks in, sits down, has a drink with the girl. I hear him say that he put him in a uber and sent him home. They walk to go to the place the other dude had reservations for them at. I honestly thought hell ya, good for you dude.
About 30 minutes later YO boy walks back in sober as the day he is born! Sits down waves me over and apologizes for whistling at me. Give us 20 bucks and buys us a shift drink for when we get off. I was off at this point and sit down to have mine with him. He lets me in on his game.
He did it all for his friend. Got 1/2 drunk played the fools and called him to come save the day. Honestly said “he is a better man for her than me. She is really just not my type”. I was stuck between awe and impressed.
They all came in about a month later looked all buddy buddy the trio of them. That asshole whistled at me again but I admit it was funny.

Olive Garden, around 2014 or so, from like 7:30 – close on a weeknight.
Middle-aged man of sub average attractiveness was sitting alone at a table with a glass of water, insisting that his date would be “just a few minutes, there’s traffic”. At around 9:15, manager had to come out and let him know that the restaurant would close at 10, and if he’d like to place a food order, he should probably do it now. He ordered a bruschetta appetizer, and said again that his date was on her way and they’d order when she got there.
9:45, this BEAUTIFUL woman walks in and awkwardly stands by his table. I couldn’t hear the conversation they had, but the man then asked for a box for the appetizer and they wound up leaving together without her even sitting down.

I’m a waitress at a mid-range priced bar/grill. Just yesterday, a younger couple came in, and as I greet them I ask if they want anything besides water.
Conversation is as follows.. Girl: may I have a Coke? Or Pepsi? Boy: God, Erin. I’m paying. Girl: water will be fine actually.
My heart immediately sank, because you bet your ass he tipped less than 10% too.

When I was in high school, my college-aged sister took me to a concert. While we were waiting for the show to start, we noticed a guy and girl in front of us who were clearly on a first date. Their conversation was so awkward that it literally devolved into talking about the weather. Brutal.
Because we’re terrible people, my sister and I decided to make fun of the couple by mimicking their embarrassing conversation. After a few minutes of our antics, the guy half-turned his head toward us with a look of pure desperation on his face, as if to say, “For the love of god, please don’t make this nightmare worse than it already is. I’m begging you.”
We stopped. A few weeks later, my sister came home from a party and told me, “Remember that guy we made fun of at the concert? I just met him. We’re going out on a date!” They are now married with 4 children.

I own a bakery, I see a lot of shitty first coffee dates and shitty people in general, but there’s one that will always be the worst for me.
This happened at my bakery maybe six months into our first year. Two boys come in, chatting normally, clearly on their first date. They’re both young, maybe 15 at most, and adorably nervous. They order at the counter and go find a table, sitting close. One of them starts holding the other’s hand, playing with his fingers, just being cute.
All of a sudden this woman comes up and starts berating one of the boys. It was his mother. She had shown up because she wanted to meet the girl because her son was being cagey about who it was (I assume he had mentioned where they were going because she wouldn’t let him out if she didn’t know.) She starts screaming and crying about how her son could do this to their family. Doesn’t he know she wants grandkids? His father would be so ashamed if he was still alive, doesn’t his father’s memory mean anything?
She then tells him that if he keeps up with this, don’t bother coming home, and then marches out of our shop. This poor boy is just weeping, while his not-even-really boyfriend is trying to comfort him, completely bewildered with what happened.

Not a first date story, but pretty funny.
On my boyfriend and my second anniversary, we went to a small dinner at a nicer place. Nothing fancy, but not Applebee’s. My boyfriend is on his phone trying to find an old picture of our first date. He dug through his phone for like 20 minutes while I sat there and talked to him, when all of a sudden two girls drop a note on our table. It said “Its a first date! Talk to each other!” And some other crap like that. Apparently THEY thought out “first date” was awkward and uncomfortable!
Now every time he gets on his phone, even though it’s almost 2 years later, I think of that date night.

I work at a country club that is up to its ears in old money that uses said old money to make more new money–the membership fees cost more than a year at my university. To say money is not an issue there would be an understatement.
Anyways, I was serving a young couple and the power imbalance was phenomenal. She was the daughter of one of the board members and the entire staff knew her (read: her father’s) club account was major money. And the gent, well he wasn’t a member, and certainly looked like he was just the average broke college student. He was wearing plain but nice clothes and she was dressed to the nines in fashion. The date seemed to go smoothly enough, nothing out of the ordinary. Until she gets up and leaves the table before I have brought out the bill. I bring the bill to the counter (knowing it is well over $300 worth of food and drinks, all things SHE insisted on ordering–2 bottles of top shelf wine, neither finished–two steaks, when he asked for the chicken and she insisted on him eating steak “like a man”) and he solemnly goes to pull out his wallet and starts tearing up apologizing that he won’t be able to tip. I mean, I’ve never had a customer cry over not being able to tip. And he further explained he was a server too and that she didn’t know he wasn’t rich and she left because he had told her about his scholarship. I was flabbergasted. And kindly reminded him that at this country club we do not take credit cards nor cash, we only charge to accounts. And so her father got a hefty bill–rest assured he signed a handsome tip to me in her name. (Club policy is that the registered guests may sign for their host member, given that the members have invited them) It was entirely satisfying. Last I heard her father cut her off, I can’t help but smile at all the life lessons she is learning–like working to go on dates.

Worked at Applebees. This woman was the worst woman I’ve ever waited on. She was needy and slurped down her iced tea like there was a world wide shortage. He was silent. He didn’t talk once except to order his quesadilla burger, and she just kept going and going prattling on. And she was mean too! Talking down about how people were losers to be servers, and how much better it was to work in a shop.
At the end, he went to the bathroom and just never came back. He apparently jetted out the side door where the to-go girls worked and gave them a twenty to give to me. Worst Woman was just sitting there and waiting for him to come back. I stood there at the servers station just waiting for her to realize he wasn’t coming back.
So after ten minutes, she just started crying, pushes her chair over, and flounced out. I didn’t get a tip, but it made my night.

I used to work at a little shitty diner place, definitely not the type of place to bring a first date. There was this guy who’d come in every Friday with a different girl. He was a very good looking dude and was alway super polite and very nice to me, but he was super awkward. The girls would look kind of skeptical as they walked in (probably because of the crappy diner scene). Every week, about halfway through the meal, like clockwork, the girls would develop these “get me the fuck outta here faces.” Thats when I would bring the check. They always boxed up there food and left right away.
I had the chance to talk to one of them while he was in the restroom. Apparently he wasn’t harmful, there was just something off about him that the girls didnt like. He’s persistence is on point though.

Had an obvious first date where the lady was grilling the guy on how much money he makes and he didn’t really want to answer. It was awkward serving steak and salad during an interrogation lol.

Late to the party here but I was bartending in NY and watched this couple that had met on Tinder have their first date sitting at my bar. The girl was a complete maniac. Kept bringing up the fact that the dude she was with could be a psychopath and could murdwr her (he had given no indication of this) and went on tinder while he was still sitting beside her at the bar. Kept telling him he was lucky that she agreed to meet him at all and she didn’t think he’d be this boring. She ordered about 5 or 6 LITs and several shots, he literally just had 2 beers. She made him pay for everything. My favourite part of this shit show was that he excused himself to go to the bathroom and left through the fire escape. Absolutely brilliant. To be clear, there was only one official entrance and exit. This dude escaped out the back and she went searching for him. Straight up thought he had disapparated out of the bar.

I was working in a small restaurant with two floors. A woman and a man came in and I had a table for them upstairs. It looked like they had a first date because they were asking those “getting to know each other”-questions. After ordering food the woman had to go to the toilet, which is downstairs. As she walked to the stairs, the food arrived. She walked down, tripped and fell all the way down knocking her head on the ground. Two colleagues immediately rushed over to her to see how she was doing. She was unconscious and bleeding from her head so they called an ambulance. I went to the man while he already started eating and told him his partner (didn’t know how to call her) fell down the stairs and that she was unconscious and that an ambulance was on the way. He walked to the stairs, looked down and walked back to his table to finish his food. Later the ambulance arrived and I asked him if he wanted to go with hem to the hospital and he said no while finishing her food as well. It was so awkward he just sat there for another 45 minutes eating, drinking, paid the bill and left. I still don’t know what kind of relationship they had and whether the woman is okay.

I have seen everything from crying to ketchup ramekins being thrown. The only obvious first date I ever noticed is as follows.
Above average looking guy sits down and says he is waiting on his blind date to show up and I tell him I’ll keep my fingers crossed.
The girl shows up a half hour late and she is…. not attractive. She was probably 120 pounds heavier than what he was looking for and her face…
I got an “oh well” look from the guy when she was in the bathroom. He didn’t say anything to me. Just had his dinner. Every time I refilled the glasses, there was conversation with both people smiling. At the end of the meal he paid the whole tab and tipped (well).
After they said their goodbye’s I caught up with the guy. I had finished all my tables and wanted to know if he was seriously ok with being set up with someone so obviously not in his dating demographic.
So I ask how his meal and date was. Then ask if there would be a second date. He laughed and said not likely. I told him that’s what I thought but they seemed to be having a good time.
He told me, “that girl probably hasn’t been on 3 dates where the guy actually paid and was genuinely nice. Why wouldn’t I be a gentleman? My friends are dicks, but she did nothing wrong and deserves to be treated like a beauty every now and then.”

Not a waiter but my friend had a date that was so bad her waiter comped the meal…
Girl and guy on a date, guy is really awkward borderline weirdo, no chemistry, my friend would try to joke with him and he would look at her dead faced, whatever. So all of a sudden two wicked drunk women come over to the table and start saying like “youre too good for him girl” “come home with us this guy sucks” “you need to dump him” AND THEY START SPRAYING HIM WITH SILLY STRING… hes like covered, they run out, he starts crying and then leaves, and she is just sitting there stunned. The manager and waiter covered her bill and she has a great story now

Not a waiter. But my first date with a girl my brother’s gf set me up with might count. The waiter was awesome.
Brother’s GF set me on a blind date with her friend who is, in her words, “totally into heavy guys.” So I go to pick her up and my alarms go off. While she’s not a 9/10 she is definitely what most would consider out of my league. I try to talk to her on the ride, at most I get noncommittal grunts of words in response.
We get to the place to eat, a steakhouse that’s noted in my area for being nice but not super expensive, and get our table. We order our food. While waiting, I try to talk to her. Simple things. She from around here, got any hobbies, etc etc. She just taps on her phone and gives me small two words answers for the most part.
Food shows up, she picks up her plate and heads to a whole other table. Tells me her friends showed up. I, apparently, was not invited. Meanwhile, she’s sitting at this other table with a good bit of expensive food. I blink for a bit, then call the waiter over and explain to him what’s up. I want separate checks. He agrees. I go ahead and pay for my food.
She begins ordering drinks. Not just for her, but all of her friends. I just finish what I can of my food. About an hour later she comes back over and says she’s ready to go. I wave the waiter down and tell him she’s ready to go. He brings her a check for well over $100. She just smiles and looks at me and pushes it towards me explaining I was paying. I push it back and tell her I’m not. Get up, smile at her.
“I’ve had a lovely time tonight. I hope you have good luck in paying your tab and finding a ride home that doesn’t involve a police cruiser.”
Brother’s GF began blowing my phone up an hour later about how could I do that to her friend. I shut her down real fast.
So whoever that waiter was, you’re the man. Keep the $20 tip.

Alright, bros, that wraps up the coverage from my end. If you want to keep on reading these AskReddit stories you can CLICK HERE to see that thread in full. And if you’ve got a story of your own that you’d like to share then, by all means, pop into the comments down below!

TAGSAskRedditDatingFirst datesWorst First Dates

Join The Discussion