Dating can often feel like navigating a complex social minefield, especially during those nerve-wracking first meetings. The unpredictability of data makes it fertile ground for memorable stories, whether it’s awkward conversations, unrelated expectations, or even just plain bizarre behavior, especially from the perspective of those quietly watching from the sidelines—like restaurant staff. Waiters in particular are often unwilling confidants or spectators of these intimate moments, witnessing everything from heartwarming connections to confusing interactions that can sometimes escalate into full-blown dramatic episodes. Their unique perspective offers insight into the complexities of human relationships and the sometimes fine line between romantic bliss and cringe-worthy disaster. Here are just a few stories from the front lines of dining service, where servers recount their experiences with some of the most awkward dates imaginable.
Anything can go wrong on a date, especially the first one. It’s natural to want to move on from an embarrassing encounter as soon as possible, but sometimes witnesses retain complete memories. Servers often find themselves unwittingly privy to all the drama taking place at the tables.
A guy reserves a seat at a table by the window, all stuffy and all. he comes in with luggage and in a suit. It’s strange, but acceptable. His appointed time is coming. They’re laughing and flirting and we kind of assumed he was going to pop the question.
Not at all. She screams at him in the middle of the night. While he was packing her suitcase, he ended their relationship. After paying, he left her alone at the table to cry.
We got her a cookie at the house. This couple was sitting here. Anyway, as soon as I begged him to put off cleaning the table, he started licking every plate! They placed several orders and he didn’t stop eating until he had cleaned the last scratches off the table. In addition, since everything took place in a common area, other patrons could also see everything.
I witnessed a date between an ordinary man and a beautiful woman. They were both in their early 30s.
He gave up on her request for a steak and ordered a salad and water instead. He also ordered a ton of ribs for himself. Then at some crazy party, he talked endlessly about his travels while his friend sat in silence. “I’ll see you on Friday, honey,” he added as he finished his ribs and left, leaving her with the bill.
One day this 20-year-old (quite gorgeous) girl asks me if we have any board games that are good for two people, gives me an order, and walks away with a smile. He comes in thirty minutes later and sadly asks me if there are any games I can play alone. She paid for him, but he showed up over two hours later than expected, gave a rather harsh order, and they talked for less than an hour.
He didn’t seem that interested in his date and he wasn’t interested in playing games. She probably thought the concept of playing board games on a first date was cool and was looking forward to it, but the guy was pretty annoying and not interested in her, which was sad. However, she was a really nice girl and came back several times with friends.
We had a guy there without a reservation at 7 pm on a Saturday night, but it wasn’t a first date. Then he suddenly announced to us that he was going to pop the question to his girlfriend. We were forced to put them in a horrible place – next to the toilet to be exact – and no one could see him as he knelt down and looked around cautiously. He and his girlfriend waited for everyone else in the restaurant to see them and either shut up or maybe applaud them, but no one did.
They went back to dinner as if nothing had happened after she nodded and expressed her disappointment.
He booked this time so I guess they didn’t mind too much! They’re back for their one-year anniversary!
At the sushi restaurant where I worked, there was a girl who went out with a different boyfriend every few weeks. Each time she ordered a portion of the same dish, which was huge and looked like a bowl of sashimi rice salad. From what I’ve seen, few individuals ever finish the whole thing in one sitting. She consumed the entire meal (chopsticks) and consistently asked for a spoon at the very end. It was always fun to see the shocked looks on the boys’ faces after she finished. One day she arrived with a guy who placed the same order as her. After they both finished their bowl, they placed another order and split it. I wish they would have stayed together but a few weeks later she came back with another man. I worked as a barista in a coffee shop where you could see the person sitting across from you in the coffee shop right over the sink washing dishes. I would have to wash the dishes and act like I wasn’t actually on a date with them because for some reason so many people chose this place for their first date. A person I know once went on his first date and chose a seat across from the dish sink that was cursed. We chatted for a bit because we knew each other and then it was like a wall came up between us and we started dating – but I still had dishes to wash.
How embarrassing!
I was waiting for a couple who were obviously on a first date; it was obvious that the woman was not very impressed with her date. The date ended quickly and I got a 5% tip from the person who paid. “That was the worst first date I’ve ever been on, and I’m sorry he pushed you hard,” the woman told me as she walked into the restaurant the next day. Then she gave me $20.
I saw one on Valentine’s Day, just now. The date didn’t seem awkward at all, in fact, it went very well. They were laughing, talking non-stop, never stopping in their conversations, and generally having fun. I was actually laughing with another server at how loud they were. Then I heard the man say, “You’re obviously not married yet, right?
Please tell me you’re not married yet,” she added “Well, actually…” and then it was VERY awkward. It shouldn’t have been a deal breaker because they stayed in the restaurant for another hour before we closed, but for the rest of the night, they were quite calm.
They hardly spoke to each other.
There was a lady in my department who was alone. She just waited. This lady was stunningly beautiful and dressed to kill.
I ended up talking to her a bit because she was obviously bored. She was smart and seemed to have a good sense of humor. Turns out she was there to meet some guy on a blind date. I was like, “OMG, what kind of man would keep a woman like that waiting?!” The guy finally rolled over looking like a crusty bro and acting like he was too cute. The woman apparently confronted him about being late because he actually got to the table and asked everyone in the restaurant if they thought she should forgive him or not. Everyone ignored the guy.
Then they talked for a while and then the guy went to the bathroom. I went to the table and said, “You don’t have to pay for drinks or anything. If you want to leave, you can just leave.” She said thank you but ended up going on with the date. They left my section and went elsewhere.
Honestly, I wanted her to leave this guy so badly.
It didn’t happen to me, but I was working while the bartender experienced it. The boy and girl had super weird chemistry all night. The guy is obviously trying to impress her by being a big badass and she looks like she’s just pretending to hate it so the date ends faster. At the end of the night, she says she’ll take an Uber home and he awkwardly drives off without her. She then waits for the bartender to return, orders another cocktail, and asks for his phone number.
I was working at a high-end steakhouse when a couple came on a first date. As I take the order, the woman’s phone rings and she answers. Her close friend apparently just broke up with her boyfriend and is upset.
The woman asks if her boyfriend can join them for dinner. The man says “Of course” and is really kind about the whole thing. The boyfriend shows up within minutes and is a crying, hot mess ordering more drinks.
The man then excuses himself to the toilet. While he’s gone, I overhear a friend expressing concern about the menu prices. The first woman then says, “Get what you want, I’ll never see this loser again.” So then I catch the man coming out of the bathroom and tell him what I just heard. He says, “What should I do?” I tell him he’s welcome to leave through the delivery door in the back and I’ll play dumb for his date. The guy expresses his gratitude and slips me $100 on the way. As the night wears on, the woman becomes upset and realizes that the man will not return to buy them food. So she waits until closing time and leaves hungry in a taxi.
The couple was shown to a table and the guy was on the phone the whole time. While I was putting together the salad, a woman came out into the hall and asked him to pack her food. She ended up paying half the bill and ran away. She told me that it was their first date and that their soon-to-be ex-boyfriend set her up. She said she would call her friend when she was leaving. When I brought him the guy’s food, he asked where he had his dinner and I told him what happened. He really thought he was in the bathroom…
A middle-aged couple:
Man: a 130-minute monologue about the cars he likes, how fast they are, and what the maintenance challenges are. Literally ran non-stop every time I passed them]
Woman: [taking the sudden silence as a chance to speak]
Woman: Well, I really like butterflies. An awkward silence
Guy: [continues car conversation until dessert]
Strangely, they returned twice more in the summer…
I was the bartender this New Year’s Eve.
The couple sits down, and the guy goes to the bathroom and comes out with his ex’s Instagram and asks his date if he thinks he’s better than the ex’s new boyfriend. The girl tried to let him know, but he kept doubling back, saying things like, “Well, I think you’re better than her, so why can’t you tell me.” At 2 a.m. she was outside in tears waiting for her mother to come pick her up.
Really hard to watch.
We had a couple: the guy kept talking about something and the girl was obviously bored. At the end, I asked if they were supposed to have one bill or separate bills and the girl immediately blurted out, “Separate!” As soon as I handed her the payment terminal, the guy started browsing Tinder on his phone.
The guy says, “What do I have to do to get a kiss? She says, “Eat a spoonful of their hottest sauce.” I warn him it’s a terrible idea. The guy shrugs at me. Tears well up, I gave him milk. I think the worst is over. Dude took off his shoes and ran to the back of the bar. And he had an accident. I couldn’t believe it until his date left.
These stories from the front lines of restaurant service reveal the sometimes daunting, often unpredictable, and always unforgettable experiences of dining on a date. From awkward introductions and awkward silences to dramatic breakups and bizarre personal habits, servers witness a unique piece of human interaction that most of us only share with close friends. The stories encapsulate the humor, embarrassment, and sheer unpredictability of dating and serve as a reminder of how public spaces like restaurants can turn into theaters of human drama.
Whether it’s a misguided marriage proposal next to the toilet or a first date ditched in favor of a server phone number, these episodes provide not only entertainment but also insight into a wide range of human emotions and social dynamics. Above all, they remind us of the resilience of those navigating their romantic lives in the public eye and the patience of the servers who follow these stories, proving that a night out can sometimes offer much more than just food.