Let's face it: Awkward dates can be brutal.
So, redditor u/Username-Checks-Outt decided to ask the servers of Reddit: "What’s the most awkward date you've seen unfold?" — because hey, they've probably seen a number of them.
In response, servers and former servers alike shared plenty of awkward dates they've witnessed firsthand. Here are some of the wildest ones:
1. This mommy mix-up:
"It was my first day at my first job as a server at a sushi restaurant (I was 17 at the time with minimal people skills). I had just checked in an older woman, who was possibly in her early sixties/late fifties, with a young man who couldn’t have been older than 25. Midway through their meal, I went to check up on them asking, 'Aw, are you taking Mom out today?' They both turned with straight faces, and the young man answered, 'She’s my girlfriend.' I whispered an apology and just peeled myself away."
2. This accidental handshake:
"I once saw a guy shake his date's hand when she reached over to grab some bread."
3. This proposal disaster:
"This guy waited for his 'fiancé' to show up, only to get on his knees and propose the moment she sat down. I immediately knew from the look on her face that things were going to go downhill real quick. I was working at Olive Garden at the time, so they ordered some pasta. Everyone could hear them arguing, but mostly you could hear the woman repeatedly say, 'YOU KNOW HOW I F****** FEEL ABOUT HIM!' The fight continued until I heard a loud 'OHHHHHH!!!' She threw an entire plate of pasta at his face. She stormed outside, he followed, and eventually the cops came and arrested the woman. I assume she was arrested for aggravated assault or something."
4. This third guest:
"We had a middle-aged lady come in with a gentleman. They asked for three menus. I went over to the table to introduce myself and ask if they were waiting for one more. The woman said no her husband is here, and then the two physically at the table ordered drinks and a water.
When I came back to drop off the drinks, her 'date' was in the bathroom. The lady explained to me that her husband had died a few years ago, and this guy (a friend) kept asking to go out. So, she said yes but insisted that her DEAD HUSBAND come with them. This is why they had three menus. She instructed me to bring her husband up as often as possible, pretend that I knew him and make sure I ask if he's having anything for dinner when I took their dinner order. She would refer to him just as if he was sitting right there. I then heard her tell this guy all night that he tries too hard and he's kind of mean.
I do not miss working in the restaurant industry."
5. This creepy order:
"I was a bartender at a burger joint. A creepy Teva-wearing older gentleman who was a regular brought in what appeared to be a younger escort. Per our operating procedures, I asked her what temperature she wanted her burger cooked. The regular then interjected and said, 'meeedium raaaare,' while staring into her eyes and licking his lips. I will never forget that."
6. This unfaithful duo:
"I once was a server at a very upscale French restaurant in NYC. One evening, a middle-aged man and a young woman 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 entrées, 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, so 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."
7. This ketchup king:
"To preface, I work in a restaurant where we make our own ketchup, and some people just don't like it. ... Anyway, a woman is seated at my table looking super excited and tells me she's on a blind date. She orders a glass of wine and waits anxiously — how cute, right? So this dude shows up on his phone, ignores my hostess, and eventually finds this beautiful woman waiting for him. He continued talking on his phone for like 15 minutes, and when he finally hung up, I went to the table. He tried to order for her — which obviously embarrassed her — and for himself, ordered a well done steak and fries.
When I brought it to him, he asked for A1 and REAL ketchup. When I informed him we had neither, he grunted and said he had ketchup packets in his truck. As soon as he walked out the door, she asked for her half of the check and her food to go. I helped her leave out the side door before he could even come back. It was awkward serving him after that. He used seven ketchup packets."
8. This horrible prom date:
"Just happened about an hour ago. It was a pre-prom dinner or something. I [assume] they had taken pictures today [so they didn't] have to do it tomorrow — guys and girls all done up, suits, sparkly dresses.
One girl got up to use the bathroom — guess she didn’t know [she got her period] — and her dress had a huge spot on the back; she had absolutely no clue. A female server runs in after her to tell her, and they explain this to her date.
He says, 'There goes my night and weekend' and just [left] the restaurant. Left her there and with the bill."
9. This awkward request:
"Wasn't serving at this time, but I oversaw this [while] waiting for takeout at a sushi place. Around 3-ish, a guy comes in and explains to the staff that he was coming in later that night with a date, and that he wants them to come out with a roll and say, 'Hi, so and so, nice to see you again. This is on the house.'
The waitress gave him the most blank look, so he explained the whole thing again, emphasizing how he would actually pay for the roll now.
I should have gone back later to see how that played out."
10. This choice of footwear:
"Probably the one where the guy’s choice of footwear was such a turn off that the woman didn’t even sit down with him. She left before he even saw that she came in.
I was a hostess at the time, so I had to go awkwardly explain to the gentleman that his date arrived and left. When he asked if she gave a reason, I had to tell him that she didn’t like his shoes. His choice of footwear? Those strange running shoes that look like feet — the ones where each individual toe goes into a separate spot like toe socks. ... He wore them with a nice grey suit. It was...really bad looking. The man was devastated."
11. This familiar coworker:
"I once had a couple on a date who were regulars. They shared a bottle of wine and were having a great time. About 45 minutes into their meal, the table across from them was seated with a large party. On my way to check on the couple, one of the people in the large party pulls me aside and asks me what their coworker Paul is doing with that young lady. I told them that he was on a date and that they've been here a few times together. The gentleman looks at me in disbelief and says, 'I just had lunch with him and his wife, Carol, earlier this week!' and then proceeds to point Paul out to the rest of the group who were all familiar with Paul and Carol. Paul was not with Carol that night."
12. All this pocket change:
"A pair in their mid-twenties were on what appeared to be a first date, where the girl was clearly way out of the guy's league, and he was apparently completely broke. I mean, like, trying-to-make-it-work-on-literal-pocket-change broke. Every time she tried to order something, he was like, 'No no...Do you guys have anything cheaper?' At one point, he had a pile of change on the table, and they were counting it out together lol. They ended up getting water and an order of french fries that they shared. She looked horrified, but to her credit, she stuck it out for the duration. Felt bad for the guy, but at the same time, I just have no idea what he was thinking."
13. This late date fiasco:
"I 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, and he orders a drink and tells me that he's waiting for [his] 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 he 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, and I told him to wait a bit. He convinced me to get them for him by telling me that he was going to drink them and leave. So, he downs the drink and gets up to leave. ...as he's turning to go, his date [arrives]. 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 drunk, like I-probably-shouldn't-have-given-him-that-last-drink drunk. They make some small talk, and it's terribly awkward. He gets up and goes to the bathroom.
Twenty minutes go by, and he doesn't come back. Finally, one of the male servers walks 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 and called him a cab. She pretty much shoved him into it and ran."
14. This super rude blind date:
"It was clearly a blind date. Neither of them were comfortable at all. I dropped off drinks, they both were polite, and then I dropped off the food, asked how everything was. The guy rolled his eyes and said, 'Well, the food is great. I just wish SHE would TALK more.' The girl’s face went tomato red, and I dropped off the check shortly after. Poor girl."
15. This breakup meeting:
"Once, a guy called and asked if our restaurant had any quiet spaces so he could have an important conversation. I just thought he meant a business meeting — nope. Turns out, he wanted to break up with his girlfriend of eight years. Halfway through, she started screaming and had to be escorted out. He ended up staying and meeting up with a new date about an hour later."
17. And lastly, this absolutely horrifying mess:
"OK, I walk into work at 5 p.m. The only people at the bar was a couple on a date. A fellow bartender walks out of the restroom, shaking his head in disbelief and shock. He immediately starts pointing to the guy and told me what happened. I walk into the men's restroom and before my precious eyes lays a Havana omelet (feces) on the floor and s*** smeared all over the restroom wall like a mosaic. I'm so livid and dry heaving at this point that a waitress asked if she could say something to the gentleman. I said sure, and she walked up to the table and asked the guy if he s*** himself and if he needs a doctor. The woman on the date then turns around to look at the waitress in complete confusion and asked what the waitress said. The waitress then replied, 'He knows what I'm talking about. He shat all over the men's [bathroom].' The woman on the date shoved her plate and drink into the guys lap and said, 'Really, Vince? Again?!' He ran out so fast before we could make him clean it."
What's the most awkward date you've ever witnessed? Let us know in the comments below!
Note: Some responses have been edited for length and/or clarity.