25 Restaurant Workers Reveal The Most Awkward Dates They Have Witnessed

Whispers, giggles, and hands barely touching across a candlelit table—this is what many imagine an ideal first date to be. Yet, real first dates often don’t live up to such dreamy standards. Waitstaff who’ve observed couples on obvious first dates recall especially awkward moments. We’ve compiled the top stories from a few threads where restaurant workers share their personal experiences, and you can read them in the gallery below.

#1

Image source: Theywerethereyouknow, Getty Images

Mid twenties aged couple on a date. First date I think but I’m not sure. Seem a bit awkward but make small talk throughout dinner. When it’s time to pay the guy asks for separate checks. Girl looks surprised. He pulls out his card and pay then goes to the washroom. I run the girls card (she already looks nervous) and it gets declined. We try again, it is declined again. I ask her if she needs a moment to figure it out (check her online banking or w/e) and she says yes. Guy comes back. She runs her card again (declined) and he sits stone faced while she is getting more and more anxious. I walk away again and when I come back the guy ends up paying for it. He wasn’t thrilled. It was super awkward for all of us, but I cringed so hard when it was obvious she had just EXPECTED him to pay for her.

#2

Image source: HappyLittleTrees17, Dongki Koh

There was a couple sitting at the bar together – seemed like it was a first date. Maybe after 30min of them being together I’m in the back rolling silverware and the dude comes running into the back and goes, “there’s an exit back here, right?” and proceeds to bolt out of the back door.

We were all flummoxed. The girl sat at the bar alone for at least another 45 minutes before she left.

#3

Image source: CigarJpug, Getty Images

Late to the party but I will share my story. Had a couple come in one night and everything seemed to be going fine. We just hired a new sever who was training and I asked her if she had any questions. She was still nervous about greeting tables so I told her she could shadow me and watch what I do. We go over to the couples table and all I hear from the new server is “YOU F*****G B***H I KNEW YOU WERE CHEATING ON ME”

Turns out the guy was her bf on a date with his side chick and he didn’t know she just got a job there. She didn’t get fired for what she said.

#4

Image source: saphs1477, Andrej Lišakov

Had a couple come in. Guy is telling woman about some real estate investment opportunities he has coming up (for himself). She tries to tell him she doesn’t think it’s a good idea and he responds with “no one asked for your opinion, you don’t know what you’re taking about”. She sat in silence for the rest of their meal, looking at her phone. When he goes up to pay, and I go clear some of their dishes away, she tells me it’s only their second date, and she doesn’t think she’s going to see him again. Couldn’t bring myself to respond with anything other than “please don’t”.

#5

Image source: hexiron, Dominik Day

Couple came into the restraunt dressed very goth. I wasn’t their server but I was running the cash register just a few feet away. They proclaimed to everyone that they were energy vampires, but not to fear them because they won’t hurt us. They said they didn’t need our food for sustenance, but enjoyed the tasted. After ordering the meal they then politely asked the waitress if she would stick around for a second so they could feed off of her aura so they could have enough energy for the night. The waitress said ok and gave me a side glance over her shoulder that I knew meant “I better get a good tip for this”… The couple clasped each other’s hands, closed their eyes, and made sucking sounds for a solid minute before leaning back in the seats and sighing as if they had just had a turkey dinner. The waitress was indeed tipped well for her delicious energy.

#6

Image source: StephyJo23, Natalia Blauth

I had a close call with an incredibly awkward story, but it ended just fine. I had a guy come in, maybe 16 or 17 and he got there first. He order her soft drink “for the lady” (his words). Then he ordered a meal for her. I was starting to get a little worried, when several minutes went by, and he was still all alone. Was this an actual girl, or was he just imagining her. Then I delivered the food, still just him sitting there. I was feeling really bad… he was a bigger guy and wasn’t classically handsome, but he seemed really sweet every time I went by the table and I wanted so bad for him to have someone special. I was so glad when later I went by there was a sweet looking girl sitting across from him, happily chatting as she ate the meal he ordered.

#7

Image source: PrawojazdyVtrumpets, Matt W Newman

I guess a husband and wife is a “date”. From the last time a similar question was asked. It’s been more like 13 or 14 years now.

> I waited tables at the Olive Garden 10 years ago. Not really f****d up as much as it was funny. A guy and his wife sat down at a table and immediately started arguing. Something about his affair and how a baby from it was costing them money. Finally it culminated as I was bringing out their salad. As I walked away I heard the wife say
>
> “Well maybe if you hadn’t boned our sons girlfriend and gotten her pregnant, we could afford to eat somewhere nicer than the f*****g Olive Garden. Oh look, the highlight of my meals, unlimited.f*****g.bagged salad. Maybe you could save up and we could go to Joe’s Crab Shack for our anniversary. A*****e.”

#8

Image source: geewhizz90, Getty Images

I was eating at a restaurant and heard the hostess ask a couple she was seating if they were out for anything special. The husband replied, “No, it’s just our anniversary.” It has inspired my father in law to drop that line almost anytime he goes out to eat now.

#9

Image source: significantmundanity, Frederick Medina

Really little guy, maybe 5 foot 4, 120 pounds comes in with a gigantic woman, probably 6 feet tall and easily 300 pounds. Both tatted the f**k up with piercings to match.

The woman orders her dish and before I get the guy’s order, he says in a s**y voice, “I think you want more than that.” She smirks at him, says, “You know I do,” and orders three more entrees. This was clearly a thing for them. They seemed incredibly happy together and became regulars at my restaurant.

I feel like I played a not insignificant role in this bizarre couple’s eating f****h for like three years.

#10

Image source: nmouchel, Good Faces

One of my first jobs in New York was managing a lounge/cocktail bar in a high end hotel. At around 3 or 4 o clock, a guy that looked pretty cheesy (slicked back hair, bad suit etc.) came up to me and demanded that he get *that* window table tonight for his date (he had a reservation for 8pm). I explained to him that I can’t guarantee it etc etc and he slipped me $400 with the “How about now” look in which I eventually caved in and told him that I’d take care of it.

He then pulled another stack of hundreds and started counting them in front of me while asking if I could go a little extra by coming over to the table when he was there with the date and pretend that I knew him from a movie. At this point, if I’ve gone this far, why not?

Sure enough he rolled around later in the evening with a blonde b***o and after they’d had a glass of champagne I approached the tables around them, checked on how they were doing before going over to him and did the whole “How are you enjoying your evening?” And before walking off I did an Oscar worthy double take with a “are.. are you… by any chance..? You must be..” at which point he had this douchy smile lapping up the “recognition” he was getting from this young dude he’d just paid off. Most importantly for him though, it worked – she was loving it – and they left shortly after and he slipped me another $600 on the way out.

#11

Image source: Puddin__pop, Getty Images

I was serving a couple probably in their mid twenties. It was Valentine’s Day and they were arguing a lot (probably because it was a chicken wing place and Valentine’s Day). The guy ended up calling me over to the table to calmly ask me, in front of his date “Do you have a high chair or a booster seat since someone wants to act like a d**n child” .

I was speechless, she wasn’t. They left soon after that.

#12

Image source: anon, Antonio Verdín

They sat down and, from the girl’s body language, you could tell she was into him. As the date progressed she closed off, then sat pretty much sideways, then was playing on her phone. The body language shift occurred over maybe 1.5 hours. He didn’t stop talking the entire time.

She did give some nods and “uh huh”‘s in response; even perked up a few times to contribute. But his monologue never stopped.

#13

Image source: AgainstBelief, Ivan Samkov

I work at a dinner theatre, and we usually do proposals where we set up a ‘random draw’ where the ‘winner’ comes up on the stage to win their prize, and are then surprised by their partner who proposes. It’s usually sweet and makes everybody in the room all fuzzy and warm.

This one guy wanted to take it further and requested to perform a song — he brought his own music and everything. We’re pretty easy going at this job, so we agree to let him do it.

We do the fake draw, the woman comes up on stage infront of a room of 400 people, and the music starts to play. Apparently this guy was a little nervous, and he compensated by having a few drinks. So what follows is a slurred performance of a song written by this guy, that seemed to focus on how he was sorry for cheating on this woman *with her sister* and at the end of it, he gets down on one knee and proposes. Usually this gets a round of applause, encouraging the person to say yes; but not after that trainwreck of a performance. The poor woman was just holding her face the entire time and starts shaking her head and says “No, what’s wrong with you?” She storms off and leaves him and our stage manager on stage to a bunch of murmuring from the audience. The only thing our stage manager can think of to say on mic is “Well, that’s that.”

The guy ended up staying for the rest of the show and had many more drinks. That was years ago and it still remains one of the cringiest things I’ve ever seen.

#14

Image source: Durnovarian, Getty Images

There’s a habit of some older couples where the elderly gentleman will order on behalf of his wife. I guess it might have been cute and romantic once, but it doesn’t work with some younger couples.

I was serving a younger couple (early 20s), who seemed pretty early into the relationship. They were ordering drinks and he orders her drink for her. Far from being dazzled by him knowing what she wanted, she didn’t want any of it

“Well I’d actually like a latte, not a coke. But fine whatever, if I don’t get a say…”

He responded quite angrily with “oh sorry, have what you want then!”

She got her latte and he glared at me. They ate and left. Not been in since, I’m sure they’re doing well.

#15

Image source: SolidVirginal, Alyssa Jane

I started working at the current restaurant I’m at a little over a year and a half ago. About six months into my job, this couple comes in, probably mid-20s. Their posture is rigid and they’re not looking at each other. They actively avoid touching each other (it’s a lunch counter-type place, so people often crowd around the counter to order if they’re in pairs/groups). It takes a while for their food to come out, so they decide to sit down and have a very serious conversation (with grave expressions, whispered tones, and everything). I suddenly realize this is a breakup lunch meeting.

When I go to bring them their food, the woman is fidgeting with her phone and looking down at her lap. The man is crying. Not loudly, but his eyes are glassy and all the ice has melted in his drink. I just go “hi here’s your food” and leave as quickly as I can. The woman gets up a few minutes later and asks for a to-go box and leaves shortly thereafter. The man just sits there, staring at his food. He doesn’t touch it and eventually leaves without getting it to go.

I don’t think I’ve seen anything sadder in my life.

#16

Image source: Yo-effing-lo, Roman Derrick Okello

I am not a waiter but a bartender, but this particular moment is something I never forget.

My shift began at 7pm and when I arrived at the bar at 6, my manager told me there’s a guy who wanted to propose to his girlfriend at this bar and he wanted me to help him with it. I said ‘Sweet, no probs.’ so the manager gave me a ring and told me to put it on top of her drink.

Fast forward to the date, the girl was wearing normal thing you would see at the bar, low cut top, black skirt and heels and s**t. The bar was pretty busy. She ordered a Long Island (f**k you Laura), so I put the ring on the straw and hand it to him. She had the ‘What the f**k mate?’ look and then he dropped on his knees. Our manager put on some romantic songs. To my surprise she threw the drink at the poor bloke and ran out of the bar.

Later I came to know that it was their second date.

#17

Image source: TheAmericanCharacter, Getty Images

I bartended at this restaurant for years that for whatever reason was a hotbed for match.com/eHarmony/OurTime first dates. Our clientele was usually in their 40s and 50s and so were our first daters.

They were always entertaining, some even ending in the parking lot for some extra curriculars. However, one stands out above all else. The couple meets and they begin talking. I got a weird vibe from the woman for most of the evening but it was a busy Saturday night and I didn’t have time to pay too much attention. Hours went by and as business died down I overheard what had to be the interaction of the night.

Guy: well this is my first time doing this online thing. I think it’s going pretty well!

Woman: oh… oh god, no. No it’s not going well. You look nothing like your picture and this conversation didn’t just make up for that. I’m going to do one more so I can justify coming out here while you Settle up with the bartender.

She proceeded to order another KJ Chardonnay. Price: 9.75 a glass. Her sixth of the night. The man, who I couldn’t help but feel for, handed me his card, signed his tab with the look of absolute defeat and then proceeded to sip his beer until the woman finished and left for her Uber.

I bought him a drink, and then he left. I never saw him again. I hope he didn’t give up.

#18

Image source: MahouHairdo, Artur Voznenko

I used to work the bar at a restaurant that was walking distance from a -very- rich neighborhood. One of my regulars was an NFL player who would bring his fiancé in a couple times a month. One day the fiancé came in alone and already very drunk. She sat on her usual barstool and started rapid-fire typing on her phone without ordering anything. I kept my mouth shut, because she was already wasted and she usually tipped me very well. I turned my back to type in someone else’s order, and I heard someone yell and then the sound of breaking glass. Turns out Mr. NFL player had walked into the restaurant with another woman. The fiancé had picked up someone else’s drink and threw it at his head.

#19

Image source: bonsai_bonanza, Mike Mozart

A guy proposed to his girlfriend at the booth across from my friends and me…at Olive Garden.
When he got down on one knee and opened the box, she was shaking her head and then just stared silently. It must’ve been a whole 30 seconds of pure silence, but it felt like an eternity.
Then, the guy proceeded to describe the ring, how much it cost, the different aspects of it, etc. Finally, the girl just went, “Nooooooo” and the guy just sat back down and they tried to finish their dinner. I caught eyes with our server and he made the most perfect “holy hell that was bad” face. Geeze that was awkward.

Edit: I still picture him saying “My love for you is like these breadsticks…Unlimited

#20

Image source: ThereandBack22, Ivan Aleksic

I guess you could call this a couple date. I was working at a wine bar when a married couple sat down on a pretty slow night. I went over the specials and they ordered. Once appetizers came out the man thought it would be a good idea to serve his wife divorce papers. I did my best to avoid that side of the bar. I did bring out tissues for the wife who was breaking down.
I ended up boxing up the dinner. The guy paid but I do not envy that ride home.

#21

Image source: Lampmonster1, Tamara Harhai

I’ve told this one here before. I worked in a resort hotel, high end, I waited tables in the fine dining restaurant. It was pretty common for people to propose there, so much so that I had a system for the whole thing. One guy came in and wanted to do the ring in the champagne thing, and I talked him into doing a dessert alternative that doesn’t result in a sticky ring and champagne on the floor. Anyway, long story short. I bring the ring, she says “Dammit, I’ve told you before I’m not marrying you.” He flips, she’s super calm about it and basically treats him like a child having a tantrum, which to his credit he was not screaming or anything, just very upset. He left, she ate the f*****g dessert, eventually he came back and paid and they left together. Super awkward.

#22

We had an older lady come in on a Saturday morning. She happily informed the server that she was waiting for a date, and ordered a mimosa to drink. About three mimosas and forty-five minutes later, we start to think maybe her date is a no show. The waitress sits down and starts talking with the lady, trying to assess the situation, see if she still wants to order and what not.

That’s when it gets strange. The lady says that her date was going to pay for the meal so she didn’t have any money, and she wanted a fourth mimosa. Meanwhile she’s cheerily looking out the window for her date, obviously nervous / excited to meet him, and very talkative. The server asks the manager what to do, so he sits down at the booth with the lady to talk with her.

Turns out, her date was Lynyrd Skynyrd and she had dementia :(

Image source: _EAT_BERTHAS_MUSSELS

#23

Image source: kiasrai, Matteo Discardi

I witnessed another waitress accidentally drop a *very* small (and plastic, like a plastic cup) container of coleslaw on a baby’s head, coleslaw side down. The mom was LIVID but the dad was laughing his a*s off, making the mom even more pissed off. The poor waitress had no idea what to do besides get some paper towels for them.

#24

Image source: Penya23, Abdurrahim Israfilov

When I was waitressing in college, I witnessed the single most embarrassing thing to happen to a person to date.

Right in the middle of their dinner (and in the middle of our Friday night dinner rush), this poor guy stands up, taps his wine glass to get everyone’s attention, and then proceeds to tell EVERYONE what a fantastic person his gf is, how much he loves her, and how lucky he is to have her in his life.

The whole time this is happening, she is just sitting there watching him with the most boring look on her face. It was so weird. Kind of like, ‘Yeah, tell me something I don’t know”.

Then poor guy pulls out a ring, gets on one knee and asks her to marry him. She gives him the most disgusted look imaginable and says “THIS is the ring you expect me to say yes to? Are you r******d? Could you be any cheaper?” Then she gets up and walks out, leaving the poor guy just kneeling there.

I didn’t charge him for the meal.

Edit: Just to clarify, this was a real rejection. Not only had they not even finished their meal when he proposed, a hostess at the restaurant knew the guy personally. Apparently it took him a really long time to get over it.

#25

They came in and the first thing I notice is that the woman was noticably older than the man but I don’t really judge about that kind of thing and I also don’t assume people are on dates. maybe she is his aunt? or they are just friends?

So I went to go ask about drinks and do the usual peppy greeting and she is super chatty. Bascially talks for him and answers questions that were straight for him. Okay, I think, maybe that’s just how they are. whatever. She proceeds to order them both hard alcohol straight..at 10 am.. I figure “eh maybe they are on a vacation together”. You never know.

It finally hit me that something wasn’t right was when she wouldn’t stop making sexual comments about the two (which is how I knew it was kind of a date). I am talking straight up things like “I am 53 but with the amount of work I have had done to my downstairs, he won’t be able to tell tonight if I am actually 23” I am watching the mans face and he looks pained.

I watch the table from afar. I realize it kind of looks like a date gone wrong, but they seemed to know each other so I am not really sure what is going on (and servers always chat and theorize about their customers in their free-time) when the man gets up and comes over to me and asks me to chat with him around the corner really discretely. So I do. He looks as me and is talking super fast as he explains that this is his boss and he has to meet with her quarterly and she just has to sign a single form to approve what he has been doing and she insists on going out for a meal and drinking and then trying to sleep with him. Every time. I was horrified for him– he looked that panicked. He said that he usually gets her to sign it before they leave the restaurant and then makes an excuse to ditch her. We made a code sign (him patting the back of his head three times) so that I could intervene when she would get far too inappropriate but honestly she didn’t change much when I would come. He also asked me to bring him fake alcoholic beverages, said I could charge him for the alcohol but to make them water or just soda.

I still think about him sometimes and wish I had gotten his name or something so I could check in and encourage him to report her, but in all honesty she probably owned the comany he worked for or something the way she spent money and looked like.

Image source: rufusmaru