We're just hoping these awkward encounters happened towards the end of the dining experience. I mean, could you imagine serving unlimited breadsticks to a woman who was just divorced? Yikes.
They Wanted to Do What With a Muddler?
Slightly different, but I am a bartender, and in an old job I worked the bar in a casino. Part of my job was to run these cocktail master classes, which basically consisted of only hen parties. Being in a rather large northern U.K city, hen parties weren’t exactly a classy affair. So our boss briefed me and one other bartender, and to our absolute disgust, we had to done one of these master classes for a group of 42. Instantly our hearts sank!! So we got it underway and it was rowdy from the outset. I was only 18 at the time, but looked a little older due to my facial hair. My colleague was a few years older but not much. The whole session was out of control, we had 42 woman on a hen party all ranging from about 35-55. Rough northern woman. I remember going over to one group of the ladies who had their backs to me, and as I went to speak to them I heard the conversation they were having.. “I’d let them both f*ck me on the stage over there” “I’d shove that thing (muddler) right up his Arse” And my personal favorite; “I wouldn’t even let me husband do me up the arse, but these two could have it any day.” Safe to say I backed away quickly. Very quickly. The only satisfaction I got that night was telling them how old I was after the borderline rape/masterclass was over. The look on their faces was absolutely priceless. (Source)
He Meant It Literally
Slightly different as I was a barman of a hotel but still relevant. A guy was drinking at the bar by himself and almost grumbling and talking to himself. As a top barman I asked how he was/if he’s had a good night. He proceeded to tell me it has been a sh*tty night and that his mates had been fighting and he had enough so came back to the hotel. He then said he just wanted to go home to see his 6 month old daughter back at home. However, this is where it gets odd because he told me that he could not go see his daughter as his wife had stabbed him in the back. Now I’m thinking his wife had cheated on him, BUT NO. His wife had literally stabbed him in the back. I didn’t believe him until he decided to remove his shirt and there it was, a freshly bandaged wound, possibly a week or two old.
I had no idea how to console a man who had been stabbed in the back by his wife… (Source)
Counting the Days
She seemed to think that the staff were some kind of inferior species and would barely acknowledge us whenever she was there, so I wasn’t surprised when she just kept talking as I was clearing things from the table. What I wasn’t expecting is for her to say: “I really can’t wait for my mother to just die. She would never let us sell the hotel, but as soon as she’s gone I’m getting out of this business. I can’t wait to have all that money.” Then they all laughed. The thing is, I knew her mother well, since she was always pottering around the hotel. She was an adorable 80-something year old woman who treated us all like her grandchildren, and would always remember who we were, and what we were doing in our lives. She wasn’t even ill or anything. The old lady had been the one who built up the family hotel-business from the ground before turning it over to her daughters when she got too old to work so hard. I was absolutely disgusted to overhear that. (Source)
She Had a Change of Heart
Years ago I was a manager of a strip club. We had some regulars. We’d usually wave the $5 cover if they tipped the staff decently.
Jim used to come in with different girls a lot. Maybe once a week. The bouncer would usually say “hey, jim” open the door for him and tell the girl taking cover charges to let him through. One day he comes in, the bouncer waves his cover, but the woman seemed freaked out. Turns out, he convinced his wife of 10+ years to go to the club with him. She had no idea he was a regular. They didn’t even argue until the entertainers started approaching him and referring to him by name, asking if he wanted to go to the champagne room again.
Wife actually turned out to be a pretty good sport about it all. They left after about an hour, arguing, but came back a few weeks later and started becoming a regular couple about once a month. I didn’t see that coming. (Source)
He Got Caught Red Handed
Not really a conversation but more of an event unfolding. One of my tables consisted of a man and a woman of about mid thirties to forties, it was lunch time. As I walk away from the table after refilling drinks two women of about the same age are being seated in the booth directly adjacent to this man and woman. I walk away as there is nothing odd occurring as of yet, as I am headed back into the kitchen I hear an extremely loud gasp and see a woman running to the bathroom with her face in her hands. The man jumps up and runs to the host stand with the woman he is with and literally crouches behind the podium, thinking that nobody could see him if he did this. Everyone is extremely confused at this point but it becomes extremely obvious that he has been caught cheating and is trying to run away. He throws some money at the host and jets out of there with his mistress, his wife comes out of the bathroom obviously sobbing and sits back down at her table. Her and her friend then proceed to order and cry for the next hour. (Source)
That Just Got Awkward
Not in the food industry anymore but when I was I had a table that consisted of a young teenage boy, his parents, and his girlfriend. I’m not sure how THEY got to this point in the conversation, but it came up somewhere between ordering their food and the food being ready that the boy and the girl weren’t virgins anymore. The table was a mess of emotions for the rest of the night. The fury of the father, the disappointment of the mother, the defiance of the son, and the mortification of the girlfriend. I’m not sure why they didn’t leave immediately to sort it all out at home but they stayed the whole meal and made things awkward for everyone. (Source)
Just Like Clockwork?
Worked at a restaurant in High School. It was a little midwestern place that served lots of pork chops and catfish. Anyway, every Friday night around 6:15, this same elderly little couple came in, and went to the same table just next to the kitchen door. Not my idea of the romantic table, but it was more or less off by itself. He would get a Budweiser, she’d get a screwdriver; they’d have dinner and talk over a few drinks. They always tied up the table for like two hours, but it was no biggie. Dinner was always $25-$30; he paid with two twenties and never wanted change. They did that every week for a year, and probably years before that. Worst thing I ever walked in on wasn’t a conversation at all. One evening, he came in alone. She had passed away. Every Friday for the next 3 months, he still came in, ordered a Budweiser, and ate dinner. Always by himself. I offered to pick up his check, the owner said I didn’t need to. They were never going to charge him anymore. He passed away a few months later. (Source)
How Did You Come Out?
I watched a kid, probably 13-15, coming out to his parents. Got to give him a ton of credit for doing that, in public, but you could tell his dad was about to flip his sh*t. Mom, looked sad, but was really supportive. Just never expected to walk up to refill a glass of tea only to hear a kid coming out to his family (Source)
If You Were a Cannibal, What Would You Eat First?
Obligatory not a waiter, but this has happened a few times to us. The most awkward instance was when she walked to us and we were arguing about cannibalism. Basically, the argument was would you eat a human if it gave you powers. If it wasn’t bad enough, we were arguing about what part of a human would taste the best as well. Another time one walked into us arguing about coleslaw — whether it was a salad or a condiment and if it should be eaten by itself as a snack. She intimately sat down with us and argued about it as well for like 10 minutes. My group of friends has weird arguments (Source)
Three Year Later, He Finally Opened Up
My story with a similar beginning… As the guy is grumbling and crying a bit, I of course ask if he is okay or needs anything. He starts to tell me how much he misses his wife. The guy was in my bar a few times so I knew him, but had no idea he was married. We get to talking about the whole thing and it turns out that on his honeymoon they went skydiving. Her parachute didn’t open. It had been three years and that night we talked was the anniversary of the tragedy. (Source)
He Knows Not What He Does
I walked up during what looked like a lull in conversation between a young couple, but the girl launched into prayer instead, asking for help in keeping her guy away from “the temptations of the flesh” and such. As she went on, eyes closed, the guy looked up at me and shrugged. I never found out what it was all about specifically, but he obviously wasn’t taking it seriously while it was a dire situation for her. They’d only gotten drinks by the time she obviously broke up with him. It was so awkward to ask whether they wanted to order… Or just wanted the check. (Source)
She Deserves It
Once was delivering drinks to two ladies and I caught, “I hate that b_tch so much. I would f_ck her boyfriend just to piss her off. I don’t care if I get an STD.”. (Source)
Do You Need a Tissue With That Cheeseburger?
When I was a busboy I went to drop off food to a middle aged married couple/ Right when I dropped off the food, he served her divorce papers and said she had to sign the divorce right away. The next hour consisted of her sitting there quietly sobbing into a cheeseburger. (Source)
Daddy Didn’t Know About Her Career Path
I worked at a restaurant and one of the servers recognized a girl at his table as being a stripper from a local strip club he had been to the night before. He for some unknown reason decided to point it out to her. She was with her dad, who had no idea about his daughters stripping. Cue crying girl and angry father… And no tip. (Source)
A Time for Forgiveness
An elderly couple sat down at a table in my section once, and the husband obviously had some severe health issues (Oxygen tank, and a nurse with him) so I guess he decided to confess to an affair during WW2 with one of the nurses in Germany, the wife was a little teary eyed at first, but forgave the guy saying “we’ve been married almost 75 years, you think I’m gonna let the past ruin it all now?” (Source)
I Didn’t See Anything
While a guy’s girlfriend was in the bathroom, I started a conversion with him about his tattoos. They were super colorful and well done. It turns out he had done them himself. He pulled or his phone to show me some of his other work. He was swiping through his gallery: back-piece, arm-piece, leg-piece, POV video of him fucking his girlfriend. Nice angle too. He was really giving it to her, her tits were bouncing and she was screaming! He shut off his phone real fast. We both acted like nothing happened. His girlfriend came back to the table, they ate quietly, left quickly, and tipped amazingly. Never saw them again. (Source)
Do You Think He Heard That?
“Ran him over and left the body there” Was the conversation I walked in on. It was a married couple. Late forties or early fifties. If it had been in regards to some sort of story I don’t think they would have that “Oh shit did he hear that?” expression on their faces. (Source)