“He Proposed And She Laughed”: 30 Wild Date Fails Restaurant Workers Can’t Forget

It’s often said that waiters are silent witnesses to the most bizarre, hilarious, and downright painful moments in people’s lives. So when someone asked the question on Reddit, “Waiters of Reddit, what ‘well this is going horribly’ dates have you witnessed?”, the floodgates opened, and the tales poured in like spilled wine on a white tablecloth.

#1

Image source: Guardian-Boy, Freepik

Not a waiter, but at the grocery store I worked at, we had a small dining area by the deli. 99.9% of the time it was only ever used by people coming in on their breaks; mostly construction workers and other retail folks.

Well one time I was put on deli duty during lunch, and this guy comes in and sits at one of the tables. Mind you, we were not a full service deli; if you wanted food, you had to order it at the counter and pick it up at the register, we did not serve or do anything table side. A few minutes later, this woman comes in and sits across from him. She looked really bewildered and confused. So I am just taking care of stuff at the deli when I hear snapping fingers. I look up, and this guy is snapping his fingers at me and is like, “Finally, can we get some menus?” I just look at him and gesture to the case in front of me and tell him that what he sees is what we have. And he looks at the lady like he’s just been slapped in the face, then stands up and points at me and calls me a wiseass. I simply tell him that we are not a full service deli, so he will need to order from the case and I will ring him up at the register. The woman at this point is very red; I remember distinctly she was a redhead and her face matched her hair. He storms over to the case (I didn’t feel threatened, it’s a deli case, which meant there was plenty of barrier between him and I, plus it was like five feet tall so he wasn’t gonna be jumping over it.

So he jabs his finger at the case and starts loudly telling me what he wants, and I am just following along, scooping and cutting and such. Then he turns around and goes, “Hey babe, what do you want?” And she just looks at him mortified and says, “I don’t even know your name, WHY are you calling me babe!?”

I’m trying to keep a neutral face and just waiting for the next order, and he just shrugs and turns back to me and tells me to make her a sandwich.

Once again, this is a grocery store deli. We did not make sandwiches. And I told him as much. And he just goes off, saying I have the bread (no I didn’t, the bakery did, which was on the opposite end of the store), the meat, the cheese, and the condiments. So I just lean around and look at the woman and ask her if she actually wants anything. She says she doesn’t and picks up her purse. He notices this and immediately runs back to the table; the speed at which he did it made me toggle the switch on the phone by the register, which sent out a “Bagger needed at Register 20.” Register 20 was code for the deli, and we didn’t have baggers, it was the code for security. Luckily he didn’t touch her, he was just panicking. But she just gets up and high tails it away through produce to the exit, and he starts to follow, but our security guy came around the corner and I pointed to the dude, so he stopped him and delayed him long enough for the lady to get clear of the store. Then he just stormed out.

She came back to the store like a month or two later and came through my checkout lane, asked if I remembered here, I said yes; I guess this guy was a total sweetheart at the office they worked at down the highway a ways, so she accepted the request for a lunch date, but didn’t know he was gonna do it at a grocery store deli (she figured the address he gave her was wrong and was just as amazed that he was actually there), and of course didn’t know how much of a complete j*****s he was. Turns out afterwards he hounded her at work so much she eventually complained and he was fired.

#2

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Not a waiter, just a barista.

the guy spent like 10 minutes explaining to her how monogamy was a trap, and she was like “oh, cool. then let me tell you about this other guy i’m kinda interested in” and then he proceeded to call her a w***e and ask how many men she slept with in cuba. loudly in my crowded cafe. at like 3pm. she denied ever visiting cuba.

#3

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Had a girl I went on with the night before come into the restaurant I was working at the next night on a different date & sat in my section 💀 She did not know I worked there. The look on her face was priceless when I said “Hey folks, my name is Ben & I’ll be taking care of you tonight.” 😂.

#4

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Had a customer who was meeting a guy for a blind date. I saw a man walk in the room, scan the room, and walk out. After a couple lonely glasses of wine, and constant checking of the phone, it became apparent that he bailed. I asked if she wanted to order a meal and she declined. I gave her a dessert and told her the bill had been taken care of.

#5

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Former waiter here. The sheer number of dates I saw that were just one person going on and on and on about themselves and not asking the other person there a *single* question was mind-blowing.

But I think the worst one I ever saw was when a guy asked the person he was with to quickly run lines with him for an audition he wanted to do. I think he thought it was some kind of flex, like he would be impressing his date by slipping in his amazing acting skills before their food arrived.

Not surprisingly, perhaps, his acting skills were not so amazing. And then he said “what did you think?!” and instead of waiting for the answer, started explaining the brilliance behind some of his acting choices while his date was forced to half-heartedly nod along and praise the performance. It was so painfully awkward.

#6

Oh I might have been one of those long ago. Well, not _horribly_, but…

I took my then-GF to dinner at a kinda specialty restaurant for her birthday, and my coworker’s wife is our server. I’ve only met the wife a couple times, and we don’t really know each other that well. But she’s nice and chats with us and makes it a really nice evening. We have a great date.

End of dinner rolls around and the bill comes. It’s my GF’s birthday so obviously I’m picking it up, so I grab my wallet…

…and get nothing but a handful of cheek and jeans…

I look around for my wallet and then realize that _I really have left it in my other pants_. I changed before we left for the date and didn’t remember to move my wallet to the new pants.

My friend’s wife is not successful at keeping her thoughts off her face. Clearly thinks this is some cheapskate schmuck b******t I’m pulling. I ask my GF to pick it up and I’ll pay her back. She’s a little worried that I lost my wallet but otherwise amused at the irony and my discomfort.

We get back to the house and sure enough, I left it in the pants that I took off. My GF laughs at me and then puts the pair I’m wearing next to the pair I left my wallet in.

So, she definitely wasn’t mad.

It wasn’t until months later that I saw my coworker’s wife again and could explain what happened. I don’t think she believed me until my GF assured her that no, I wasn’t a cheapskate, just a dummy.

Image source: PDX-T-Rex

#7

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I was the female half of several dates where the guy just did an extensive monologue throughout the whole thing. You wonder if you are going to get lockjaw from trying to smile politely. This happened in my 20s and happened in my 70s – those kind of guys don’t change. 100 years from now it will still be the same.

#8

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Not a waiter, but witnessed absolutely mind-bending “date”. Guy brought his girlfriend and a couple of her girl friends to an Irish pub for St. Paddy’s Day. They racked up a decent bill of $150. He makes an excuse of some sort and the table gets noticeably tense. The flustered GF paid cash on the table and went to the bathroom while the rest of the group collected their things to leave amid a pretty chaotic St. Paddy’s celebration.

She came back and the money was missing. The wait staff came to collect the bill and she starts freaking out. The BF is loudly swearing he doesn’t know what happened to the money. The staff is understandably concerned about how the check is being paid. The manager comes over.

The entire packed pub witnessed the commotion, her friends are super embarrassed, the GF is crying as it was a lot of money to her and the guy was freaking out about where the money was and why wasn’t she paying the bill. The staff confronts him about the bill and he screams at her using her name over and over to not let them get away with harassing him. While he’s restrained by a bar back, another waiter searches the BF’s pants pockets and finds the $150.

They call the cops on the BF and drag him out while he is thrashing about. The girl is a trembling, crying mess and the friends are shell-shocked. But the staff switches. They console her, one of the waitresses sits with her and several of the patrons pitched in to cover her bill. Soon, other patrons are also consoling her and offering support.

Her remaining group stayed for another hour or so after the cops came, getting to experience the kindness of strangers. But she had an uncommon name and whenever I hear it now I still hear that s*****g yelling it out over the packed pub.

#9

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I’ve witnessed two failed marriage proposals. One was uneventful, the proposal happened and she quietly said no. They both left looking dejected. As for the other one, he was an obnoxious jerk and she seemed over it. He proposed at dessert, she said no, he tried to argue and they ended up yelling at each other in the rain outside the restaurant. She was right to turn him down.

#10

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I was waiting tables at a mid-range Italian place that tried *really hard* to be upscale—dim lighting, wine pairings, Sinatra on repeat. One night, a couple in their late 20s comes in, and right away the vibes are *weird*. The woman looks uncomfortable; the guy’s wearing a *trilby* and calling her “milady” unironically.

They sit. He orders for her without asking, insists she try the Chianti “because it has notes of rebellion,” whatever that means. She clearly hates it. At one point he goes, “So… how many kids do you want?” I am not exaggerating, we are *maybe* 12 minutes into the date. She laughs awkwardly and says, “Wow, jumping ahead a bit?” and he deadass replies: “Well i just feel like we have something cosmic.”

She spends most of the rest of the dinner either pretending to text or sipping water and making eye contact with me like, *please save me*. I check in with them and she says, “Actually, can I get this to go?” He looks crushed, and says, “But we haven’t even had the tiramisu. That’s when I was going to ask you out *officially.*”

She just grabs the bag and says, “I think I need to be somewhere that’s not here,” and tips me *$20* on a $30 bill.

He stayed and ate the tiramisu by himself, said “her aura was just too guarded,” and asked if he could leave his number in case she called the restaurant. She did not.

#11

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It was these 2 kids that I’d guess were 12-14. The boy’s mom drove them to the restaurant. The mom planned on f*****g off to the bar so they could enjoy themselves.

The boy would not let her leave the table no matter how many hints her and the girl tried to throw. I saw that he was physically holding his mother under the table.

The boy was so nervous that he barely talked to the girl. He mostly talked to his mom…and the girl mostly talked to his mom. It was so painful to watch.

#12

Funniest :
Guy was on his phone the entire meal name dropping like crazy. When dessert cane he finally hung up and said oh sorry I was just on a really important call with Mark Wahlberg. For the next 15ish mins, his date pretended not to know who that is while he became more and more desperate to make sure she knew he was a big deal. He named like 30 movies, he sang some marky mark, he even said his brother was a new kid on the block. This absolute queen just kept going yeah no sorry not ringing any bells. New kids on the what? Who is Martin Scorsese, is he new?

Saddest :
I worked for a while at a kosher restaurant that catered to a very ultra traditional crowd. I saw a lot of first meetings for arranged marriages. The one that stuck out the most was this guy who spent the whole date criticizing her while she sat silently and avoided eye contact. He ate a full meal but would only allow her to have water. Their families sat at the next table and nobody spoke up for her. I wanted to flip their table over, it was so horrible to watch. I hope they didn’t get married.

Image source: Mtldoggoagogo

#13

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I’m not a waiter, but the couple at the next table was on what was clearly a first date. I was facing the same direction as she was so i couldn’t see her face, but i could see his and could hear everything he said.

And when i say I could hear everything HE said, i mean i don’t even know what her voice sounded like because the guy literally wouldn’t shut up. I don’t think she said a single word the entire date. He just talked AT her nonstop for a solid hour. Didn’t ask her a single question. Didn’t pause to even eat his food, just talked while chewing. I cannot even imagine what was going through her brain while this was going on….

#14

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I remember this one time a couple were on their first date, the restaurant was empty, and the guy was a regular, so I made sure that they had a great experience. Hooked them up with a free app and some wine, let the lady play her music on the speakers. When I was bringing them dessert, she got a phone call and she was told that her father had died. It went from a near perfect evening to probably the worst night of her life.

#15

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Had a table where the guy ordered a ton of food, and when the bill came, he started making excuses about how he ‘forgot his wallet’ and couldn’t pay. The girl was mortified, especially since she had already paid for her own meal. She looked like she was ready to crawl under the table.

#16

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I saw many good dates, bad dates and everything in between. The saddest was a couple that seemed like a good match. Lady was so excited but the guy was insecure but successful. Persian dude in early thirties. He got there early and it was a great date spot. I chatted with him while he nursed a drink to cool the nerves. He was a very down to earth guy and i felt like we genuinely connected.

She shows up and was so excited… until he talked about himself and his career for the next 90 minutes. I wanted to scream at the guy to ask a question but he was trying to impress her and was a totally different guy.

#17

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I have 2 stories, both of which I’ve witnessed myself.

First off, sat in a Thai restaurant in the trafford centre with my wife, and there’s a table with a young couple there. She was 18 or 19, he was about the same age. The conversation seemed somewhat forced as HIS MUM WAS WITH HIM, saying nothing with a face like thunder. And when he went to the toilet, she followed him. When they’d left her alone, she just sat there texting disconsolately.

Second, at a Chinese restaurant in Oxford. Again, a young couple sat next to us, but he spoke incessantly about how well traveled he was. I don’t think I heard a single word out of her at all, it wasn’t a conversation, he was just subjecting her to a monologue. He spoke at length about how he’d visited Third World Village and lived there for a month. (Didn’t name the village or country, didn’t say A third world village, he made it sound like a theme park. Said he’d eaten a dog while there. Said he had experience teaching underprivileged children as he’d taught in some of the worst schools on the isle of wight. For anyone unfamiliar with the isle of Wight it’s very affluent, very pretty and rural. I imagine that the roughest schools there have slightly tatty wisteria, and serve inferior caviar at lunch.

Poor girls.

#18

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We had this one older lady come in every week. She wore a different wig every time. Should would ask to sit at the same exact table and ask that we would act like we’ve never met her before. Then, throughout the day, sometimes the entire day, she would have multiple dates. These men would just fawn all over her. If they did not bring her flowers, it was a wrap. She would ask that we help sneak her out of the restaurant until the guy left. Sometimes it got real awkward. She never paid. She also asked that we only address her as Tiger.

It was weird.

#19

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I’ve seen a bunch but the best was when a guy brought in a canned Pepsi and just asked for a glass with ice. He then offered one to his date.

It did not go well. .

#20

Busboy at a really nice restaurant. Middle aged couple sitting at a two top on an outside patio. Across from them was a boisterous group of 6, who were throwing money around. Bought a bottle of Dom Perignon for the couple to apologize for being so loud, as they left. Apparently, the husband brought his wife to the restaurant to be in a public place to tell her he’d had an affair. Telling her this over the champagne. She blows up, as you’d expect. Loudly berates him and starts asking about what occurred sexually between him and the other woman. All the wait staff walked by at 0.5 speed and convened in the bar to share what they heard.

Image source: smitty143143

#21

Not date but breakup!!

I had a couple that would come in almost weekly, for like over a year , always mega nice and generous tippers and then one day they were both at the table, not saying much, with the young lady tears streaming down her face and the young man with an incredibly solemn thousand yard stare and inknew they were breaking up… but my question was like why would you do this at the restaurant of your nice memories?? Or in public at all?? .

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#22

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Not a waiter, I was just eating with family when I was about 14 or something. The section of my table didn’t have anyone opposite as my parents sat next to me and there was this couple 18-20ish who seemed to be on a date.

The guy seemed to be trying to talk to her, but she would not put down her phone. Just texting constantly, talking a picture of the dish. Every now and then, she’d wave her hand like “Sorry, just sending a quick message” set down her phone for all of 30 seconds before picking it back up and messaging again.

I remember she excused herself to the toilet, the guy looked around the place and saw me looking at him. He half-shrugged his shoulders like “can you believe this?” I could only shrug in agreement. I think he finished his food quickly and ended the date soon after that, she hadn’t even touched her food yet.

#23

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When I was in college I was working in a bar where the man left his phone in his jacket, and left the jacket on the chair when he went to the bathroom. His girlfriend/wife immediately went for it, and within the minute and 45 seconds he was gone she apparently found what she was looking for and as he returned she started yelling and flipped the high top table over. She ran out with his phone and he ran after and we just comped the check because no one was interrupting that.
Edited to add: I hope it was a scam, they deserved every single bite for free, but they didn’t stay long enough to enjoy the fruits of their performance if so. Also I watched all the color drain from that man’s face and he looked like a fish swallowed a golf ball, so an epic performance if it was staged.

#24

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As one of the closers, if anyone came in between 9-930 no big deal but I’d make it obvious we were closing at 10pm.
Anyone in after 930pm I’d tell them kitchen closed in 15 mins and after 940 I’d just tell everyone it was to go only, the managers didn’t like this, but I’m the first to greet the people and I’m doing all the work and that last hour; I’m the Captain now vibes lol.
So a nicely dressed guy comes in at 845 asks for a table for two, declines anything but water til his date arrives. I did what I could to stay busy but after 45 mins and now it being 30 mins to close, I approached and warned him the kitchen closes in 15 and he said his person was walking in. A woman in yoga clothes, walks up and flips down opposite him; never looking up from her phone.
He ends up having to order for both of them because she’s not present beyond physically being at the table. I get the order in and as I’m passing to another table I hear him quietly pleading she give him a chance – at what idk I was pushing some old folks outta my party booth and didn’t hear. Their food comes up and as I’m dropping it off she says “it’s just not the way I thought it’d be, so I don’t want to do it anymore.” And his face was crushed, body language said he was flatlining.
I automatically bring boxes with the check, and as she hadn’t touched her food I wanted to save time. I pretty much knew, dessert wasn’t gonna happen but the manager was out front and I had to try that final upsell or be banished to the back section with the flickering lightbulb.
“Just ask if they want dessert, just ask if they want dessert!” I said it the whole way to their table and with a giant smile on my face I asked “so guys, you thinking about DIVORCE TONIGHT?!” cue my horrified gasp and the girl just looks up at me from her phone and says “see Justin? Even the waitress knows this isn’t working.” And poor Justin just looked at me as I literally tossed the checkbook and boxes and said “I’m so sorry.. Jesus!” The manager gave them a discount and I never again offered dessert.

#25

I might accidentally be someone else’s story. My boyfriend and I went out to celebrate out first anniversary of dating. We thought it’d be fun to dress fancy, so we definitely stood out a bit.

While we’re waiting for the bill, the conversation turns to acting techniques. BF says that the best way to portray anger isn’t to make a stock “angry” face, but to let your face go completely slack.

I give it a try, and apparently give BF the most withering look – right as the waiter comes up behind him with the bill.

The poor guy did a complete 180 and basically hid behind the bar for several minutes while I died laughing.

Image source: TorggaFrostbeard

#26

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Girl was actively on a dating app during the date and I felt like she wasn’t being very discreet. A dude once tipped me $100 to give a drink to a woman at another table and he was there with his wife. Life is wild.

#27

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While working at a little dessert shop, a regular brought her date in. Things seemed fine, but later that week he came in alone and tried to get my number. I, of course, told her as soon as I could and she was sad, but grateful.

The worst I’ve ever witnessed I was just another person eating next to a date. I was actually catching up with a friend and we wound up not talking most of the night and just listening to a woman become increasingly more erratic explaining how badly she wanted to m****r a bunch of different people in her life. Her date just sat there like a deer in headlights.

#28

A friend of mine had a really bad one while waiting tables at a small town restaurant.

Saw the dude get down on one knee and open a box. His date said “that isn’t the ring I wanted” and walked out.

Image source: Soyl3ntR3d

#29

So, not a waiter but am sure we’re some waiter’s story. OH and I are sitting in a restaurant after dropping our son off at university to start his first term. I’m feeling all the feelings – happy for him, of course but also so so sad. We order and I start crying. OH holds my hand but I just cry some more. He squeezes my hand and says ‘sweetheart, you need to stop crying because people are thinking it’s me.’ Sure enough, lots of angry eyes on OH who they likely presume is breaking up with me or admitting some peccadillo or other. We laugh about it often, ten years on. Still miss my baby boy. 😂.

Image source: JustJezebeluk

#30

Not a waiter, but was working at Panera in high school. I was wiping down tables, and this guy and girl were having a seemingly normal conversation. She then starts playfully doing footsie with him, and he just explodes: “I TOLD YOU NOT TO TOUCH MY SHOES! I CAN’T F*****G STAND YOU!” And then just stormed off. She just sat there stunned, and we made eye-contact and I did one of those 🤷🏽‍♂️ while breathing in through gritted teeth:.

Image source: euphorickittty