Waiters Reveal The Most Awkward Dates They Have Ever Seen At Their Restaurants

Restaurant servers overhear a lot of interesting conversations. Birthday celebrations, business meetings, anniversaries; there are a lot of reasons people go out to eat.

Dates can be some of the most interesting, or some of the most awkward.

Reddit user u/yummygumdrop asked:

"Waiters and Waitresses of Reddit; what is the most awkward date you've ever witnessed on the job?"


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.



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.



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.



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 bathrooms. Dude called me over, he paid the bill, got up and left. So there is this



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."



I was a new server waiting on a large party. Of course, everyone wanted water so I came out with a large tray of water glasses.

That sh!t is balanced. The weight is equally distributed so that the tray is easy to carry. I start passing out waters, but one guy reaches out and takes a water glass for himself and f---s up the balance of the tray. The remaining six glasses of ice water tip behind me and all of them fall on a girl at a two top table...in a white shirt...on a date. She wasn't just a little damp. She was drenched. I felt awful and she was mortified. Her date had no idea what to say and all I could do was apologize non stop and go find her a towel.




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.



Ice cream shop employee, so not quite a waitress, but the couple were at least 16 and were being chaperoned by the girl's mother, who insisted on taking photos every few minutes.

Not just candid photos, but posed ones. Taking their ice cream and getting out the door with it took nearly 20 minutes because the mom wouldn't stop.

The girl seemed pretty embarrassed by her mom's behavior, and the boy looked immensely uncomfortable with the whole situation.



This girl and guy came into the restaurant I used to waitress at, and I could tell right away she wasn't into the guy but that he was really into her. She was on her phone the majority of the time, and every time I'd walk past or go over to them she was talking about an ex. Even asked me to take a picture of them and she said she was going to post it for him to see. When I would see him talk, she either didn't seem to notice because she was on her phone or would just nod/shake her head. The guy looked so uncomfortable. He seemed really excited at the start of the date, but I could tell he how disappointed he was by the end of it. She didn't seem interested at all, and it was clear she had gone out with him just to piss her ex off.



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.

Edit: he had already signed their tab and given me a tip. Not that it would have stopped me from doing it if he hadn't already paid. I made bank at that place on Saturday nights.

Incidentally, I witnessed several of my friends' boyfriends come into that bar with other women. A few walked out when they saw me, but most didn't. Call me a b!tch, but I told on them every single time.


What's the most awkward conversation you have ever overheard in a restaurant?