He Didn’t Catch This One
“I used to work the bar at a restaurant that was walking distance from a very rich neighborhood. One of my regulars was an NFL player who would bring his fiancée in a couple times a month. One day the fiancée came in alone and already had some drinks. She sat on her usual barstool and started rapid-fire typing on her phone without ordering anything. I kept my mouth shut because she was already wasted and she usually tipped me very well. I turned my back to type in someone else’s order, and I heard someone yell and then the sound of glass shattering.
Turns out Mr. NFL player had walked into the restaurant with another woman. The fiancée had picked up someone else’s drink and threw it at his head.”
“Used to bartend/waitress at a pub back in the day.
One evening a guy comes in and sits down at a table for two. I go ask him if he wants a drink. He orders a drink and tells me that he is waiting for a girl he’s meeting for a date to order food.
He waits for a bit and I served him a couple drinks. An hour passes, he’s looking at his phone occasionally and drinking. He finally comes up to the bar after an hour and a half and tells me he thinks he’s been stood up.
That’s rough man. He orders a couple drinks neat and pounds them back. He’s starting to look and sound considerably worse for wear at this point. He ordered a couple more drinks, downs them and gets up to leave.
Who just so happens to walk in the door as he’s turning to go? His date. She was still wearing scrubs and looked pretty disheveled. She apologized up one side and down the other for being late.
I then got to serve one of the most awkward dates ever. He was really out of it like I probably shouldn’t have given him that last drink. They make some small talk and it’s terribly awkward. He gets up and goes to the bathroom.
20 minutes go by and he doesn’t come back. Finally, one of the male servers walk up and tells her that her date is having some troubles in the bathroom. He was sitting on the toilet bawling.
We asked her to get him out of there. We called him a cab and she pretty much shoved him into it and ran.”
This Waitress Never Saw This Coming
“So about a year into my current job, a young woman about my age starts coming in with one of her (also female) friends. She’s very beautiful–blonde, fantastic body, extremely sweet and bubbly. The second or third time they come in, they’re dressed to the nines–girls’ night out! They order a round of very strong drinks a few times and they chat me up a while. I guess also being a young woman, I’m disarming? I don’t know, I try to be social but I’m awkward sadly.
After a while, they get toasted–and the blonde girl starts laying it on me thick. I’m kind of lost, I get flirted with somewhat regularly (drinks + food + relaxed people = funtime?), but I’ve never been flirted with by another woman. They leave eventually and the blonde girl departs with a blown kiss and a wink. I’ve never been so flustered and yet oddly curious in my life.
She comes in every so often after that, progressively more sober and progressively more flirtatious. She’s touching my arm, batting her lashes, the whole nines. My male coworkers (at the time, I was the only woman working there) are insanely absorbed in this and constantly ask me for updates. She keeps flirting and I keep not knowing what to do except weakly go ‘oh yeah hahaha I’ve got a boyfriend.’ She’s never deterred.
But then! It happens!
She comes in a few months after this all started–WITH A GUY. And she does not look happy. I was working a shift that I usually didn’t cover on an odd day, so she was shocked and visibly displeased when I waited on them. The guy with her is totally oblivious and a very chipper dude. I introduce myself, say ‘oh yeah (woman’s name) is one of our regulars!’ The guy goes ‘oh yeah, my fiancée never stops talking about this place! I totally thought we should come!’
Oh no. I put all the pieces together– I’m her gay crush, but she’s engaged to a man. I have never seen a human being redder in my life as she was. I quickly take my leave to get their food. Throughout the night, he gets up to leave to go to the bathroom/order more drinks/whatever, she’s adjusting her hair and touching up her lipstick. It’s a disaster. I’m dying inside.
They come in a couple more times until she suddenly announces (without looking at me) that she’s been accepted to medical school, so they’re moving. And I’ve never seen her since.”
Dine And Destroy
“I bartended at this restaurant for years that for whatever reason was a hotbed for Match.com/eHarmony/OurTime first dates. Our clientele was usually in their 40s and 50s and so were those on first dates.
They were always entertaining, some even ending in the parking lot for some extracurriculars. However, one stands out above all else. The couple meets and they begin talking. I got a weird vibe from the woman for most of the evening but it was a busy Saturday night and I didn’t have time to pay too much attention. Hours went by and as business died down I overheard what had to be the interaction of the night.
Guy: ‘Well this is my first time doing this online thing. I think it’s going pretty well!’
Woman: ‘Oh… oh god, no. No, it’s not going well. You look nothing like your picture and this conversation didn’t make up for that. I’m going to get one more so I can justify coming out here while you settle up with the bartender.
She proceeded to order another KJ Chardonnay. Price: 9.75 a glass. Her sixth of the night. The man, who I couldn’t help but feel for, handed me his card, signed his tab with the look of absolute defeat and then proceeded to sip his drink until the woman finished and left for her Uber.
I bought him a drink, and then he left. I never saw him again. I hope he didn’t give up.”
A Better Celebration
“This was such a horrible moment that myself and a few other servers tried to make the best of. I used to wait tables at a local family pizza restaurant. One evening in the summer around 8:30 pm after the dinner rush is mostly over, a nicely dressed couple (probably late 20s, early 30s) comes in and is sat in my section. My co-workers and I can see that they are dressed way too nice for here, and the woman has a clearly puffy/red face like she has been crying. Not wanting to mention it, I go into the usual ‘hello, welcome to such-and-such, my name is…’ and get their drinks and let them look at the menu.
After a bit of talking with the man while the woman is in the bathroom since we were slow that night, I find out it is their wedding anniversary. They had plans to eat at another very nice and expensive restaurant about 5 minutes away, but even though they had a reservation they had waited about an hour or two to get seated, and then waited another hour without getting so much as a glass of water. So they left since both were starving. At this point, I’m horrified at what happened and want to do everything in my power to make them have a great night, with the husband feeling the same. So I mention it to my co-workers. A crafty server gets some colored paper and makes a few small roses with some scissors and puts it in a small vase we usually use for pens. Our bartender chips in to get them two glasses of our nice local craft brew. The wife is holding back tears at this point, but they are happy tears.
Meal is delivered to their table and they definitely look like they’re having a great time in the modest family pizza place. We also got them a dessert. Once they’re finished (around 9:30 or so) the husband tries to pay. Except all the servers and bartender have already chipped in and paid for their meal about 20 minutes ago. So I tell him not to worry about it, that this one is on us. I think we made them both tear up, but we were not about to let that previous restaurant ruin their anniversary.”
Famous Last Words
“I was serving a couple probably in their mid-twenties. It was Valentine’s Day and they were arguing a lot (probably because it was a chicken wing place and Valentine’s Day). The guy ended up calling me over to the table to calmly ask me, in front of his date, ‘Do you have a high chair or a booster seat since someone wants to act like a child?’
I was speechless, she wasn’t. They left soon after that.”
A Hilarious Twist Of Karma And Irony
“I once was a server at a very upscale French restaurant in NYC. One evening a middle-aged man and a young woman are sat in my section, clearly on a date. You could tell this woman was his mistress by the way they interacted with each other. They were high maintenance but pleasant enough. Right after they had received their entrees, the man looks across the way to another table and loses all the color in his face. His date noticed and turned to see what he was looking at.
The man’s wife was at another table, also on a date with her side piece, on the other side of the restaurant. The wife sees him and has the same expression on her face, which very quickly turns to rage. She briskly walks over to his table and starts whisper-yelling at him, pointing her finger right in his face. He starts to do the same back at her. This isn’t a very big restaurant, everyone knows what’s going on and the atmosphere gets icy. The man’s date is just staring at her plate, absolutely mortified. The wife’s date pretends nothing is happening and continues eating. Eventually, the wife storms back over to her table and wolfs down her dinner (no exaggeration, she was like rage eating). He sits down and his mistress won’t speak to him for the rest of the meal. This is a fine dining restaurant and they ordered multiple courses. Having to clear, crumb, and reset their table two more times was less than fun. He left a very big tip and apologized on the way out.”
She Was Not Prepared
“Mid-twenties aged couple on a date. The first date I think but I’m not sure. Seem a bit awkward but make small talk throughout dinner. When it’s time to pay the guy asks for separate checks. The girl looks surprised. He pulls out his card and pays then goes to the washroom. I run the girls card (she already looks nervous) and it gets declined. We try again, it is declined again. I ask her if she needs a moment to figure it out (check her online banking or w/e) and she says yes.
Guy comes back. She runs her card again (declined) and he sits stone-faced while she is getting more and more anxious. I walk away again and when I come back the guy ends up paying for it. He wasn’t thrilled. It was super awkward for all of us, but I cringed so hard when it was obvious she had just EXPECTED him to pay for her.”
Savage Restaurant Massacre
“Woman, who had a bit of a baby bump, thought she was getting a proposal from her guy. Instead, she was given a folder full of pictures. They must haven’t been good pictures as she went pale and wide-eyed. The guy took them back and then walked out.
She was crying and frantically tried to go after the guy but he already drove off. I saw her standing outside frantically calling anyone she can on her phone, asking for a ride. She was picked up an hour later.
It turns out she had been cheating on him, as another server told me she saw one of the pictures and it was her and a different guy in bed together. I always wondered who the father of that baby really was…”
The Big Issue With Blind Dates
“I was sitting at a brewpub enjoying a very delicious IPA in the corner booth, writing some silly jokes for stand up that night. I am always aware of my surroundings and find myself looking up or over whenever someone new comes in. I briefly looked up and saw the hostess talking to a man and not taking him to a table. Whatever. I go back to writing. A minute passed and this man takes a seat at my table and says ‘Amber?’ I look up at him VERY confused. He repeats, ‘Amber? Fet Let?’… I lost my composure (as Fet Life is for people with fetishes looking for a hookup) and laughed through my ‘no.’ Just what a ballsy move. He got up very embarrassed and that’s when the girl at the booth next to me very sheepishly said: ‘I’m Amber’.
I hope to god the hostess saw that exchange.”
A Little Too Aggressive
“This was a Tinder date. Guy keeps ordering for the girl (like that is weird anyway but when you are legitimately having dinner with a stranger, why would you think that’s ok?!)
He ordered her drink (Cabernet) which she corrected to a glass of water. Then he ordered her some soup, which she stated she didn’t want. Then he ordered her meal (shrimp scampi), which she corrected to chicken marsala because she is allergic to shellfish.
She was very sweet and I’m assuming was trying to give him the benefit of the doubt. Until something took a turn and she poured her water on his head and stormed out.
The one good thing about him though… he tipped very well. Almost 60% tip on an already expensive meal.
I would kill to find out what he said to make this seemingly sweet girl a full glass all over him.”
Obligatory Retreat From Society
“I had two morbidly obese regulars that we referred to as Mr. and Mrs. Cheese Sauce. They usually ordered food to go and one fateful night I learned why. Mr. Sauce ordered a bacon cheeseburger, loaded waffle fries with an extra side of cheese sauce, a coke, a 5 scoop ice cream sundae, and a coffee.
While drinking his coffee and finishing his sundae, he asked for the check and when I returned with it he was gone. Mrs. Sauce said she was going to make the husband sit and wait in the car for being irresponsible. I was confused until I had to clean the table and found a butt crack shaped poop stain on the vinyl booth.”
Match Making Mother
“My sister was single and the server was attractive. So my mother’s train of thought was ‘I’m going to hook up my daughter and this server.’ Cue 40 mins of me trying not to be noticed as my mother asks him if he’s single, looking to date, showing him pictures of my sister. Luckily he was pretty chill about it, he answered the questions and said that he wasn’t looking to date, it was just very awkward.
What’s even worse is we CAME BACK with my sister, and my mother introduced her to him after we got him as a server AGAIN. My mother isn’t a crazy person but I was cringing off the charts. Thankfully it was just this once with this one server, I haven’t seen her do it again.”
“Had a couple come in. The guy is telling the woman about some real estate investment opportunities he has coming up (for himself). She tries to tell him she doesn’t think it’s a good idea and he responds with ‘no one asked for your opinion, you don’t know what you’re talking about.’ She sat in silence for the rest of their meal, looking at her phone. When he goes up to pay, and I go clear some of their dishes away, she tells me ‘it’s only their second date, and she doesn’t think she’s going to see him again.’
Couldn’t bring myself to respond with anything other than ‘please don’t’.”
A Serious Turn Of Events
“I am a barista and had a gay couple sit at my bar while on a date. They were super friendly and talkative and seemed to be having a great time. It was really slow and they were asking us a lot of questions. My coworkers and I had a competition to see who could make up the best drink and had them both try it and vote. They thanked us for a great time and walked to the parking lot.
About fifteen minutes later, one of the guys came back in the restaurant in tears. His boyfriend had broken up with him in the parking lot!
He never said what happened, but he has become a loyal customer and brought new guys to our coffee shop several times since. He’s much happier now.”
Caught In The Romantic Cross Fire
“Oh god, I feel bad just remembering this.
A couple was seated in a booth all lovey-dovey. They shared a dish of something. A bit after I look over and they are gone. I walked to their table and I notice he forgot his coat and on the table, there is a note that read: I had a really good time but I have to go, I’m sorry!
Didn’t understand at first but 5 seconds later the dude walks out of the washroom. I’m standing there with his note in left hand, his jacket in my right hand and fully understanding that she ditched the dude as he went for a wiz. I look at him and said, ‘I’m sorry man.’ His face changed instantly. I should have given him a hug. As he left he still wished me a good day.
She was all smiles before so I don’t get it.”
An Empty Glass Of Hopes And Dreams
“I started working at the current restaurant I’m at a little over a year and a half ago. About six months into my job, this couple comes in, probably mid-20s. Their posture is rigid and they’re not looking at each other. They actively avoid touching each other (it’s a lunch counter-type place, so people often crowd around the counter to order if they’re in pairs/groups). It takes a while for their food to come out, so they decide to sit down and have a very serious conversation (with grave expressions, whispered tones, and everything). I suddenly realize this is a breakup lunch meeting.
When I go to bring them their food, the woman is fidgeting with her phone and looking down at her lap. The man is crying. Not loudly, but his eyes are glassy and all the ice has melted in his drink. I just go ‘hi here’s your food’ and leave as quickly as I can. The woman gets up a few minutes later and asks for a to-go box and leaves shortly thereafter. The man just sits there, staring at his food. He doesn’t touch it and eventually leaves without getting it to go.
I don’t think I’ve seen anything sadder in my life.”