She arrived first, which she always did. The place he’d picked was fancy and an hour out of town, and she’d tried to talk him into something casual instead—coffee, a walk in the park—but he’d insisted. So she sat down, ordered a strawberry lemonade, and told the waitress she was waiting on her date. The waitress was warm and friendly, wished her luck, and seemed genuinely sweet.
Then he showed up, and the waitress’s mood shifted like a curtain dropped. She gave him attitude when he ordered. He spent the whole night trying to push alcohol on her, asking repeatedly what she was really drinking, why not just a little vodka, and she kept saying no, she was fine with her strawberry lemonade. The waitress kept topping it off for free every couple of minutes, hovering nearby, never letting him out of her sight.
She kept complimenting her too, which was sweet but strange. The guy got pricklier about it. He asked, half-whispered and angry, whether the waitress was going to charge for all the free refills. He looked furious and uncomfortable, and she couldn’t figure out why the waitress was being so cold to him.
So she excused herself, went to the bathroom, and waited for the waitress to come in. The waitress looked at her and said, quietly, that he came in every other weekend with a new girl. Every single time, the girl would leave acting very drunk, stumbling and slurring. She suspected he was drugging their drinks.
So she’d been switching hers out and keeping an eye on him. She walked back to the table and confronted him. She told him to empty his pockets. He didn’t have anything on him, but he admitted the truth anyway: he got girls drunk so he could pressure them into sleeping with him.
He said it like it was normal, like it was just how these things worked. She stood up and left. The waitress walked her to her car. She tipped the waitress every bit of cash she had, and she still thinks about that woman sometimes.
She never forgot her. Another waitress, another restaurant. An Italian place in 2006, and this was an obvious first date. He’d booked it himself, and he’d requested a table in a secluded corner because, he said, the acoustics were perfect.
She arrived and asked to move to a table by the window. No big deal. He was annoyed. They ordered a carafe of house red with their meals.
Then he started in. Anything she said, he turned into an achievement he’d somehow already accomplished. He commented on her order, mentioned how fattening this or that was, and then dropped that his family owned a vineyard and he knew a good red wine when he smelled one. He sent back the house wine and ordered the most expensive bottle on the menu, then spent a good while talking about its bouquet and clarity as if he were a sommelier and everyone else in the room was deaf.
When dessert came around, she’d had enough. He told her she shouldn’t have any, said she might end up with stretch marks. She was a bit overweight, but not by much, and that was the line. She stood up, called him a condescending piece of work, told him he didn’t know a damn thing about wine, and then let it drop that her own father was the restaurant’s wine supplier.
The house red he’d turned his nose up at was the exact same wine as the most expensive bottle on the menu. Every word was true. He had nothing to say. The full check was his.
One server saw a woman come in first and directed her to the bar. Her date showed up late, no ring, and the two introduced themselves awkwardly. They ended up in her section. Small talk seemed to be going fine.
She asked the woman if she wanted another martini, and before she could answer, the guy cut in and said, “The water will be fine for her. ”
She didn’t even have a chance to redirect. The woman stood up, went off on him for thinking he could order for her, apologized to the server and the whole dining room, and walked out, mortified. The guy stayed and ordered dinner for himself, ate alone, tipped well, and left awkward as hell.
Another place, a café that did cakes and sundaes. Friday evening, Valentine’s Day around the corner, busy with couples. She noticed a woman in a black dress, hair done up, makeup perfect, followed by a guy in casual clothes staring at his phone. He wasn’t paying attention to where he was going.
He stopped every few minutes to text. The woman ordered something like ten things from the counter, glancing back angrily at him the whole time; he didn’t look up once. The server and the cashier exchanged a confused look. She brought the cakes out.
The guy was slouched in his chair, still on his phone, and the woman was staring at him with pure murder in her eyes. She set the tray down. He finally looked up, opened his mouth, then went right back to his phone. By the time the server got back to the counter, the cashier touched her shoulder and pointed.
The woman was devouring every slice of cake in front of her, ignoring the silverware, barely stopping to breathe. She demolished one piece after another. Then she walked to the counter with chocolate and cheesecake smeared across her face, slapped a fifty-dollar bill down, and left without a word. The guy sat there with his phone down, staring at nothing, for what felt like forever.
A diner, one server telling the story. He was the only male server. A guy came in and tried to hit on one of his coworkers. She was too nervous to wait on him, so she begged him to take the table.
The guy made some joke the server didn’t care about, but she found it demeaning, and she lit into him. Not loud, just very irritated. Then she finished, ran back to the kitchen, and hid. The guy didn’t know what to do.
He finished his meal and left a huge tip, apparently to impress her. The server thought about it and figured, sure, he gets why dating was hard for her. She had an on-again, off-again boyfriend and kids with him, and he was Black, and she wasn’t. Plenty of guys didn’t want to date a woman whose kids didn’t look like them.
But honestly, the server said, he wouldn’t have wanted to date her anyway, and not for that reason. She was genuinely crazy. On her last day of work, she had to hide in the walk-in freezer so her manager, also a woman, wouldn’t beat her up. Another guy told a story from about fifteen years ago.
He was at a trendy restaurant with a friend late at night. The only other table held a couple on a first date. The woman was attractive and had a voice that grabbed him immediately. He kept staring, listening, and it became clear she wasn’t interested.
Twice she took calls and left the table. The guy figured it out too and asked for the bill. She was still on the phone, later revealed to be begging a friend for a ride home. He paid, vanished, and on the way out, the woman was still waiting outside.
He and his friend started chatting with her, and they connected instantly, mostly over how cringey that date had been. She almost laughed herself sick. They stood there talking for about an hour, and it felt like they were the ones who’d been out together all night. She tagged along with them to a nearby club, met his friends, and they ended up dating for three years.
One server had a great memory. If someone told her something once, she remembered it. She could handle two tables of eight without writing a single order down. She got a couple, gave them the menu and the specials, and the guy started hassling her immediately about not taking notes.
She told him not to worry, there wouldn’t be any errors. He kept pushing. Then he told her he would only tip her if she didn’t mess up his order. His date wouldn’t look at either of them.
She just said that if there was a problem, the manager was in his office upstairs. It was two drinks, two appetizers, and two entrees. Everything came out on time, exactly as requested. He told her she’d failed anyway.
His date looked mortified. The server didn’t care. Guys who try to bully the waitstaff to look important just end up looking like something else. Another story, not a first date, but the worst couple a server ever saw.
A young man, maybe nineteen or twenty, rented out a private dining room that seated about forty. He invited his entire immediate family and his girlfriend’s entire immediate family. Both sides sat across from each other in an awkward silence, and he proposed to his girlfriend in front of all of them. She had no idea it was coming.
She ran out of the room screaming and crying. Her mother announced she would never allow them to marry. His father made some racial remarks about the girlfriend’s mother. Both families sat there in total shock, staring at each other.
Then the girlfriend’s mother decided to get blackout drunk, fell over, and knocked over one of the tables. Everyone kept ordering food and drinks, expecting the young man to pay the whole bill since he’d brought them all there for his big surprise. But he was mortified, his girlfriend had rejected him, and he bailed. His father was left with the check.
Needless to say, there were many split checks and very few tips. The server said it was terrible and traumatic, a night she would never forget. A host at another restaurant seated a couple in their mid-forties at the bar. Their server was the host’s roommate, and she came up and whispered about how weird they were being, making out at the table.
A few minutes later, a furious man stormed in and stood at the host stand, scanning the room. She asked if he needed a table. He glared at her, then marched over to the couple at the bar and sat down across from the woman. She looked horrified.
He whisper-yelled at her. All the host could make out was that she was on a date with a man she worked with, and the furious man was her husband, who had found out through a friend. The host stood five feet away, watching. The husband’s voice got louder.
The host grabbed a passing server, told him what was happening, and got the biggest cook on staff. The cook went over and told them to leave. The woman and her husband left. The other man sat there, confused, staring at all the uneaten food.
After a few minutes, he came to the host stand and asked for his bill. When it was printed, he paid, said, “I’m sorry for the disturbance. I didn’t know she was married,” and left. The host felt terrible for him.
He’d seemed really into her. One server watched a couple in their mid-twenties on an obvious first date, and they got along well. Halfway through the meal, they were holding hands over the table. Cute.
Then the guy lifted her hand and kissed the back of it. She seemed a little confused but went along with it. A little while later, he did it again. Then again.
The woman looked uncomfortable, and they were no longer holding hands. When the server went back to check on them, the guy was full-on making out with her hand, tongue and all. The woman looked like she wanted to die, looking anywhere but at her date. The server went over and asked if they needed anything.
The guy stopped. The woman yanked her hand back, grabbed her bag, and left. One server worked at IHOP for three months. An old acquaintance came in with a date.
At the time, the server had a stutter that came out when she spoke too quickly, got stressed, or hit hard words. She walked up to the table, said hi to her friend and the date, and immediately stumbled over the greeting. The date did that little condescending laugh everyone has heard, then repeated her words back, mocking her stutter. The server watched her friend physically recoil, her face a picture of pure disgust.
The server brushed it off at the time, and it only bothered her for a second, but even years later, she still hadn’t forgotten. She knew in that moment her friend wouldn’t go on a second date with him. One story came from a former restaurant. Reservation for six.
A young guy came in a few minutes early, nervous, admitted it was a first date and he hadn’t had many. Sweet, really. The girl arrived half an hour late and got very drunk. Midway through the meal, she answered her phone and started talking about her date, right in front of him.
She said things like, “Well, he’s not usually my type. I don’t exactly like him, but I figured why not. ” Right in front of him. The young man looked devastated, walked up to the server, paid his bill, and left.
He was a really nice guy, and the server still sees him at the place she works at now. One veteran bartender had a more hopeful one. He worked a medium-range Italian place, and he’d seen first dates go wrong because one person drank too much. The most memorable was a woman who started downing rum punches.
The waiter kept bringing them without flagging anything, even after the sixth one. The bartender asked if they were all going to the same person, and the waiter said yes. He thought, oh no. Sure enough, she ended up throwing up all over the bathroom and locking herself in.
When they got the door open, she was passed out, covered in her own mess. No cab would touch her, so the guy took her home. He came back a week later and said they were going on another date. The bartender was skeptical.
They’ve been married for about fifteen years and are absurdly happy. She just avoids rum punches now. Another steakhouse story. High-end place.
A table of two, and the server assumed they were a couple. They took forever to order, talked through several rounds of cocktails. Finally, the woman ordered a filet mignon, and the guy ordered the most expensive steak on the menu. Right before the food came out, the guy got up and walked toward the bathroom.
The server ran the food to the table, and the woman sat there alone with everything in front of her. He never came back. Twenty minutes passed. The manager asked what was up.
The server said he was in the bathroom. The manager checked, no sign of anyone. They put the food under the warmer for about an hour, and the woman sat there alone the whole time. Finally, the server walked over and asked if everything was okay.
She broke down. It was their first date, they’d met on Tinder, she’d suggested coffee because a steakhouse felt like a lot, but he’d insisted. And while they were talking, he looked at his phone, said his daughter had an emergency, and left. She’d been texting him and getting no replies.
She kept saying, over and over, “What’s wrong with me? ” The server reassured her as best she could. Then she went to the manager and asked about the check. He hesitated because the tab was $250, but the server convinced him to comp it all.
She boxed up the food, including the guy’s expensive steak, and brought it to the woman. She stopped crying, thanked her, and left. After writing the story, the server wondered if they’d somehow swindled her. One couple at an Asian fusion place in Durham watched an obvious first date.
The woman mentioned she’d expected her dish to be spicier. The guy snapped his fingers above his head, loud enough that half the restaurant turned around. The waitress rolled her eyes and came over. He demanded they recook the dish and make it hotter.
Then six Thai waitresses surrounded the table, calling him worse than garbage in their own language. The other couple’s girlfriend, who spoke Thai, translated. It caused a massive scene. The woman’s face turned red.
They took her plate away, and she had to sit there with no food while he ate. He eventually realized he’d messed up and stopped eating, tried to apologize, but the damage was done. They brought her a fresh plate, and the two ate in silence. It was definitely their first and last date.
One bartender at a high-end steak joint got a pretty brunette at the bar. She said she was waiting for a date. A few minutes later, the guy arrived carrying a large bag. Their conversation was forced from the start, painful to listen to.
Then he reached into the bag and pulled out an album containing his Pokemon card collection. He set it on the bar and thumbed through every page, lovingly describing each card, trying to educate his date in the ways of Japanese Pocket Monsters. To be fair, the bartender said, the guy was passionate. The woman feigned an emergency and called a friend to pick her up.
The guy stayed and ate a plain hamburger at the bar. Both of these people were in their mid-thirties. One bubble tea shop near a college got a lot of first dates. The worst was a guy who looked about seventeen to nineteen, meeting a girl around the same age.
They played a board game, talked. And his mother sat at the table next to them the whole time, just staring them down. The icing on the cake was when she went up to them at 8:30 and announced it was time for the two of them, her and her son, to head home. He was visibly angry but said goodbye to the girl and followed his mom out.
The girl came up to order another tea, and the server asked her about it. The girl was glad to explain. The mother had essentially injected herself into the entire date, interrupting their conversation and criticizing her son’s behavior the whole time. One server had a two-top across from a family of six.
The two-top was a couple in their mid-forties, maybe fifties. The server was delivering food on a large tray, and someone had been berating him for not using the legs with his big trays. So he grabbed a pair. While he was setting them down, a stacked plate on his tray shifted, and everything pitched toward the family of six.
He panicked, tried to stop it, and the tray went backward. He didn’t hear a single plate shatter. He turned around, and the woman at the two-top had red sauce on her face, mashed potatoes on her chest, and broccoli all over her lap. He started blubbering, “I’m so sorry, ma’am, please stand up and let’s get you cleaned up.
” He had two managers helping. She was the politest person in the whole restaurant, insisting it was nobody’s fault. Her husband finally said, “At least wipe the sauce off your face. ” She laughed, got up, and everything on their ticket was comped, including the alcohol.
It was the only tray he ever dropped, and they never made him use the legs again. The couple came back a week later and asked for him specifically. The husband told him they were celebrating thirty years together that night. The server felt horrible until the husband told him that on their first date, she made spaghetti and accidentally dumped it in his lap.
He’d told her it was karma. They had a huge laugh and a free meal. One bartender worked at a place famous for its wings, not the wings he’d have preferred, but whatever. He got an obvious Tinder date at the bar.
After a few drinks, they were clearly into each other. He was happy for them. But as everyone knows, stuff happens, and it was about to happen, literally. He passed by and asked if they wanted another round.
They both eagerly agreed. While he made their drinks, he heard the guy ask, “What do I have to do for a kiss? ” Cute. The girl thought for a second and said, “Eat a spoonful of your spiciest sauce.
” When the bartender brought the drinks back, the guy, grinning, asked for the spiciest sauce they had. The bartender tried to talk him out of it. When that didn’t work, he grabbed his phone and started recording. The cook brought out the sauce, and the guy tipped back the whole ramekin.
At first, it was fine. Then the tears started streaming down his face. The bartender got him some milk. He thought they were over the worst of it.
Five minutes passed, and he was wrong. The guy kicked off his shoes, stood up, and ran toward the back of the bar. As he ran, something started escaping down his pant leg, leaving a trail all the way to the bathroom. The bartender couldn’t believe it.
The guy refused to come out until his date left. He never got the kiss. To be fair, the bartender noted, they really were nice shoes.