11.
“I worked at a higher-end restaurant as a busser for a while, and eventually was given a chance to serve in the bar area while a jazz band played. Most of the tables were just drinks and appetizers. My first shift a woman in her 40s or 50s came in with a tall, dark, and handsome guy no older than 30. Nothing wrong with that in my eyes, but all of my interaction with them was the woman talking down to me on some sort of power trip (maybe to prove to her guy that she’s an alpha female or something, dunno) and her ordering everything for her date. They had cocktails, ordered a bottle of wine, and had a couple entrées. She ordered ahi tuna, RARE. She was very insistent on the rare, so much so that I put blue rare into the computer so everything would be fine. She sent back 4 separate plates (all too well done) to the absolute horror of her date. I informed her after the second that they wouldn’t be taken off her bill, and she scoffed and made some comment about how she’s loaded and it doesn’t matter. After the four plates, she sent the last one back and asked for a shrimp cocktail instead. I left them to enjoy the music, brought the check, and when I came back to pick it up, her date was gone, and I don’t mean, went to the bathroom or went for a smoke, all of his things were gone and he was nowhere to be seen for 30 minutes. She apologized to me and asked if I could take the ahi tuna (~$45 each) off of her bill. Told her to pound dirt. Not really, but my manager did. Next day she wrote a 500 word review about me, using my first name, on the restaurants Facebook page. My boss printed it out, framed it, and I still have it today.” –IDKimjusttheintern
12.
“I legit saw the guy try to roofie the girl. Like not even trying to be hidden about it. He did it right in front of me. The girl went to the bathroom and I was cleaning the table next to them. I saw him take the powder out and slip it inside the drink. Another thing too, it was a pizza place. Who tries to roofie someone in a pizza place!” –tottaly_not_masters
13.
“Guy and girl came in, super weird chemistry all night. The guy is obviously trying to impress her by being a huge douche and she looks like she’s just pretending to not hate it so the date will end faster. At the end of the night, she says she’ll take an Uber home and he awkwardly leaves without her. She then waits for the bartender to come back over, orders another cocktail, and asks for his phone number.” –BigFuturology
14.
“Worked at a pub connected to a brewery in college. Dude comes in with a stunning woman, I mean she’s absolutely gorgeous. Whole time they’re sitting at the end of the bar, and you can hear the guy talking about how he has a room for them next door at the hotel in downtown. So they decide to go to the brewery next door, gonna pull a little dine and dash. They got over there and didn’t realize we are on the same system, so he orders a couple of beers, and the bartender on the brewery side asks if he wants to add it to his tab. He looks over confused and says “what tab? I’ve never been here.” She prints off the restaurant bill plus his brewery tab, it’s like $80 or so. He just blankly stares at the poor bartender, flies off the handle. The girl he was with ended up paying for it. They walked across the street and to the hotel, he has already invited her up, she stalls until her Uber gets there and then just dipped out. Kinda funny, kinda awkward, but that’s what you get for dine and dash.” –stocky_stegasaurus
15.
“I used to work at a sushi restaurant in Anchorage, and there was a girl who would come about once every few weeks with a different guy. Every single time, she ordered a heodubbap, which is like a rice-salad-sashimi bowl, and it was GIANT. I’ve only ever seen a handful of people ever finish the entire thing in one sitting. She would finish the whole thing (with CHOPSTICKS) and always ask for a spoon towards the end. It was always fun watching the guys look stunned when she finished. One day she came with this dude that ordered what she did, and when they both finished the bowl, they ordered another and split it. Wish they had ended up together but she came back with a different guy a couple weeks later. She never paid.” –themerrypaek
16.
“Not a first date, but when I first started bartending I had a woman who was very obviously stood up. She got there, ordered a drink, and would look around every once and a while. I saw her use her phone a couple times and her mood just got sadder until she finally put her phone upside-down on the bar and ordered food an hour later. I wiped what I could off her bill then paid the rest myself, told her it was on the house. In my career it’s happened two more times, once with another woman and once with a guy. I did the same thing. Nothing sucks more than eating alone and defeated.” –fraxiiinus
17.
“The guys card declines. I didn’t want to embarrass him so I waved him over near the credit card machine so it would look like he needed to go to the bathroom. He told me to try it again and I assumed he was going to move money over on his app. He went back to his date. Card declines again. The machine prints a receipt that states the reason for decline… “insufficient funds”. I keep trying 4 more times. I go over to the table and say “I’m having an issue with the card, might be our machine, do you have another?” I walk away with the new card, and it declines. I wave him over. He gets up angrily and I’m guessing now the date has caught on. He proceeds to berate me saying that it must be our machines because HE KNOWS HE HAS MONEY! He starts making fun of me questioning if I know what I’m doing. He is doing this in front of his date I’m guessing to save face. Gives me another card. Declined. The date pays.” –justacomment12
18.
“More sad than awkward, but here goes (for context, I am a woman in a long-term relationship and was NOT hitting on the girl or anything) : One day this (very cute) 20-ish girl comes in, orders, and cheerfully asks me if we have any boardgames that are great for two people (I worked in a concept bar where we had 700+ boardgames you could play as long as you ordered something to drink). I show her a few games, she choses one and sits at a table near the entrance. 30mn later, she comes and sadly asks me if we have any games you can play alone. I give her one and tells her if her date doesn’t come, I’ll give her a free shot. Another 40mn later, she comes back, I give her the shot and we talk a bit, then she goes back to her table to play by herself (It was a busy night, otherwise I would have played something with her, she seemed nice and was obviously sad). The guy ended up showing up almost 2hours late, ordered a bit rudely, she paid for him, and they spent less than an hour talking. He wasn’t interested in playing a game and didn’t really seem interested in his date either. He left early, she stayed a bit to talk with me as I started to clean up, I offered her another shot and drank one with her, and she left all sad. I imagine she was excited for her date and thought the boardgames bar was a cute, fun idea for a first date, but the guy was so rude being late and not showing any interest… just sad. She came back a few times with friends though and was really a nice girl.” –Grog_Bear
19.
“Once, as a high school teenager, while waiting tables at a now defunct Mexican restaurant chain (think Applebee’s, but tacos), a first date came in. They seemed unable to converse. It was super awkward. Painful to watch. Well, at one point the woman asked for a refill of her tea. I dutifully went and got the pitcher and came back to fill her glass. While pouring, i literally dropped the entire pitcher, a full gallon, of sweet, sticky tea directly onto her. It went down her shirt. Her skirt. It was everywhere. She was completely and utterly soaked. My newly blossoming career as a server flashed before my incredibly stoned eyes. I apologized profusely. I brought her out like 4000 napkins. Her date was dumbfounded and probably thinking “didn’t think this could get worse, but here we are”. Well, she cleaned up the best she could. And they ate their meals. And, magically, they began talking. They started looking at each other like a new couple looks at each other. They laughed. They enjoyed their shitty food. She dried out. They left the restaurant an hour later, with her arm in his. They gave me the biggest tip I had ever gotten. I got $20 on a $20 bill, in 1996. Somehow, my idiotic, high, blunder, turned the worst first date ever into the best first date ever. I like to imagine them now as happily married, parents of 7 lovely children, who love telling the story of the moron who poured an entire gallon of tea on her, 25 years ago.” –AmishTechno
20.
“The date I saw started off great. I was playing in a band at a small club. There were about 30 people in the club. A couple who had been sitting close together in a corner booth disappeared together into one of the bathrooms. In between songs, when it was quiet in the club, the bartender yells, “They better not be in there fucking on my sink!” The whole place turns and stares at the bathroom door, and as we’re staring, the couple emerges, smiling at first. Then they look around, see everybody staring at them, and their faces turn a deep color of shame. They quickly paid their bill and left.” –ThatGuyFromOhio