“It Was So Painful To Watch”: 68 Dates So Awkward, Even The Waitstaff Needed A Drink After

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When a date is going poorly, the number one thing we want is for it to end, not to play out the inevitable conclusion in front of spectators. But if the meeting is set to take place in public, certain obligations might not allow us to run away.

One Reddit user who goes by the nickname Common-Sprinkles9328 recently asked all the waiters on the platform to describe the tables they served where love went to die — and they delivered. Here are some of the most painfully awkward, hilariously disastrous dates they had to witness… because someone had to bring the bread while the night crumbled.

#1

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.

Image credits: Silly_Accident3137

#2

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.

Image credits: NillarGorillar

#3

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.

Image credits: Master_Air_8485

#4

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.

Image credits: HorrorAvatar

#5

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.

Image credits: PammySexy777

#6

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.

Image credits: esoteric_enigma

#7

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.” 😂.

Image credits: Ben–Jam–In

#8

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.

Image credits: UknowNothingJohnSno

#9

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.

Image credits: vtxlulu

#10

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. .

Image credits: ElHamburglare

#11

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.

Image credits: tammorrow

#12

Quit my job like 4 months in because I worked at a real romantic like place with a lot of dates and my single a*s high school self could not handle that

but one time I was pouring some tea into this guys cup and he’s talking to her saying “your so pretty” and stuff I turn to the woman’s and then she’s like “you looked better in the picture” and I laughed then they both stared at me.

Image credits: OddPaleontologist14

#13

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.

Image credits: Guardian-Boy

#14

Man tried to order for his date, she didn’t like that but it was early in the date so she said nothing, he ordered an expensive appetizer that she didn’t want, only he ate it. She looked not impressed but still seemed to be trying to feign interest. Came time to order dinner and he tried to order for her, something expensive, surf and turf. She said no thank you, she was a vegetarian (something established before the date) and wanted the vegetarian dish. He didn’t back down and insisted she have the surf and turf. She again said no, she wouldn’t eat it. He countered with “he could afford it so why not?!”
She left.

Edit for more info: the vegetarian meal was written down but there wasn’t an opportunity to put the order in.

2nd edit: alright, fine; I was that woman on the date, I never said I wasn’t but maybe I sort of lied for internet points and to also relay to women it’s okay to say no and walk away, even if they pay for things or insist on it. Yes, at the time I was a bartender/server; and yes what happened to me is 100% accurate, I was just the woman and the waitress responded exactly how I described it. Also I left a tip just in case he didn’t and thanked her on my way out.

Image credits: MissHillary

#15

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.

Image credits: drulaps

#16

A woman was engaged/married with a ring on her finger and thought she was meeting someone for a networking HH but the guy thought they were on a date.

Image credits: 828passenger

#17

Not a waiter, but I did once see a woman storm out of a date in a very nice restaurant. The couple was seated at an adjacent table to me. She got up abruptly and left, just before the food was served.

The waiters seemed to handle it very discreetly: they brought a cover to keep her meal warm in case she returned, and after a generous interval, quietly took her plate away. The guy waited for a while before forlornly eating his own meal and asking for the bill.

Image credits: InbhirNis

#18

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.

Image credits: Fearless-Spread1498

#19

Not a waiter but the one that lives rent free in my head was from a table next to mine at a birthday dinner. Very romantic setting, man bends down on one knee, proposes, the woman accepts happily crying, the whole restaurant erupts into applause, and the couple sit down to continue their dinner aglow with happiness. About 30 minutes later the woman gets a call on her phone and she’s gone for another full 30 minutes or so, and when she comes back the two of them are super stony faced and don’t look at each other and don’t speak to each other at all for the rest of the meal. Their table was also positioned smack in the middle of the restaurant so they also spent the whole meal being side-eyed by the whole restaurant as we wondered what the f**k happened on that phone call. Turned me off the idea of public proposals forever.

Image credits: orcastrait

#20

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 murder a bunch of different people in her life. Her date just sat there like a deer in headlights.

Image credits: jperscrpers

#21

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.

Image credits: Bissandraa

#22

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.

Image credits: doctor4th

#23

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.

Image credits: MissHibernia

#24

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.

Image credits: pacmanfunky

#25

I had a table of 4 on a double date. They looked… very religious. The two women were both overweight and homely. The two men were, looks wise, more attractive than their wives, and also very, very into each other. My gaydar is, well, fabulous and let’s just say it was telling me the men were the ones actually on a date and their wives were just along for the ride.

I don’t know if I’d say it was going horribly. Felt bad for the women.

I had another table that was a ton of teachers out for a school dinner. One of the teachers’ boyfriend tagged along and told us he was going to propose… in f*****g Applebee’s… in front of all of her coworkers. He was sweaty and nervous the whole time. She said yes.

I still f*****g laugh about that. Who the f**k does that? It was so f*****g cringey and I enjoyed every second of it.

Image credits: Picklesadog

#26

Mines just the amount of dudes that think it’s okay to propose on valentine’s day in an olive garden lmao.

#27

Rich, well-known, middle-aged business owner brought in a smoking hot young 20 something, and she only wanted to talk to me (also 20 something waiter).

Needless to say, he didn’t leave me a good tip.

Image credits: IsaacJacobSquires

#28

Dude came in with a woman, and any time I overheard any part of the conversation, the guy was excitedly talking about his sister. “Oh, and this one time, my sister…….” “My sister has this great story……” “You would love my sister…”, you get it. The woman he was with was very polite, and just nodded and listened to all the great stories about her date’s sister. One of my colleagues had overheard some of the sister talk too, but they didn’t realize I had also heard it. At one point, I went up to them, put my hands under my chin, smiled and said “tell me more about your sister”. Making fun of customers made the job not suck, and I was very good at it. Colleagues loved me, and customers were indifferent.

Image credits: shameonyounancydrew

#29

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.

Image credits: Winter-Nebula83

#30

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.

Image credits: Debtcollector1408

#31

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….

Image credits: Recent_Obligation_43

#32

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?? .

#33

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.

#34

Was sitting at a bar with two friends, one female. A girl sits near us and tells us she’s meeting a tinder date for the first time. She tells my female friend that if it’s going terribly she might ask her to go to the bathroom which would be codr for get me out of here. The dude shows up and is as weird and unpleasant as can be. We are waiting for the signal like it could be any moment but no, she is eating it up. He even goes to the bathroom and she’s gushing about him and we’re like ok wtf.

#35

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:.

#36

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. 😂.

#37

Here’s a backwards situation for you. A weird assumption. My friend and I, both ladies, went to a buffet-style restaurant. They had a magician going around to all the tables, looked like fun. He was indeed stopping at the tables with no children so he wasn’t there only for kids. But he just wouldn’t come over to ours. Finally my friend goes to the restroom and I gave our waitress a tip for the magician specifically and asked her to have him come over. She said “does she want to see the magic or does she want to hit on him?” Like, wtf! Neither of us had ever been to this restaurant before so I don’t know if they thought she looked like “the type” of person to hit on him or what but really, we just wanted to see some magic tricks. He finally came by, did a few tricks, no one hit on anyone, and it was fun!

#38

My husband and I met while waiting tables and every year we go to the restaurant on our anniversary, so maybe this counts. A few anniversaries ago we were seated next to a couple on their first date, and the guy was so obnoxious that the girl handed me her phone when he left to use the restroom and told me to talk to guys on her Tinder for her because I obviously had better taste than she did.

#39

Bartended for a long time. Well known bachelor in town shows up and sits at the bar. I greet him like normal, he says he’s waiting for his date, another local. Before she shows up, I notice he’s got two bud lights in front of him that I didn’t serve him. He’s got two more in his pockets. I said, “Jay, you can’t do that s**t here. You gotta go.” He shrugged it off and walked out. Pretty sure that was their first and last date… and the first time I realized how much of an alcoholic he was.

#40

Not a waiter but I managed a late night burger place right next to the biggest nightclub in 3 towns.

I was running orders and I look up and see this blinged out diamond necklace almost blinding me. Then I see the guy and it takes me all 10seconds to recognize him. It’s a legendary quarterback like top 10 ever

I bring him his order and him and his girl sit down. In about 2 minutes she just starts berating him about how broke he is, how he’s not the man he used to be and just going for like 5 minutes while dude just ate his burger and fries. This totally pissed her of and she throws her not so happy meal at him. He continued eating. She just explodes and walks out of the restaurant leaving him there to finish his food. Dude never batted an eye.

#41

I saw a woman stick a fork into a man’s hand once. Loudly banging the table, all the way through his hand. Horrifying.
The man wailed. Everyone else gasped. I heard a couple of oh my gods, too
And, she threw food.
It was their anniversary, a special date.
Ambulance and police came.
He still had to pay the check, poor guy. Left a huge tip. We had to clean up a mess of blood, bread, wine. Luckily, their salads and entrees hadn’t arrived yet!
A few weeks later, they were back at the restaurant, still together.
I moved on to another job, but, I bet they are still together if they haven’t killed each other yet.

#42

Guy was in a metal band and spent the entire date blasting his music from his phone for her to listen to. It was bad. She did not look like the metalhead type (could’ve been, but it would’ve been a little unexpected the way she was dressed) and was just chuckling sort of awkwardly the entire time.

#43

Saw this one date at the bistro where the dude was full-on analyzing the menu, like he was hunting for typos instead of just picking a meal. Meanwhile, his date’s doing the vanishing act, scrolling her phone, probably texting her escape route. Classic case of wrong priorities. Shoulda gone for simpler vibes!

#44

A place I worked had the “break-up” table. It was a half-booth for two and I guess because of that it was where blind dates and break-up dates always ended up. And it was true about 90% of the time.

“Yo LeprosyMan, you got two at table 11!”

Oof. Even the kitchen knew to hold on the entrees or desserts until I gave a thumbs up.

The other 10% were anniversaries or (I kid you not) failed proposals. It sucked.

#45

Well i have seen a woman who was definitely in her late 20s have her parents secretly sit in the restaurant to watch her go on a date….very interesting to say the least. I have no idea if the date had any clue. The girl was sweet but allergic to everything under the sun.

#46

An older woman on her first date after being widowed, bursts into tears 5 minutes in, guy she’s with tries to console her which only seems to upset her more so he stands up and loudly says, “Know what. f**k this” and walks out. The woman sat there for another hour drinking water and weeping. 3 or 4 more tables get sat near her and after a few minutes asked to move.

Woman never ordered anything, didn’t tip must’ve had 10 water refills, left the table a mess.

#47

I was eating at a restaurant once and the guy at the next table over was breaking up with his GF. She was crying, but for some reason everyone thought he had proposed, so everyone kept walking by and saying “congratulations!”  It was t*****e to even witness. .

#48

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.

#49

There’s always a date where one person continuously talks about themselves non stop the entire time. Like 45 minutes straight of just talking about themselves & never lets the other person speak.

It’s usually a guy doing this, but I see women do this too sometimes.

#50

Im a bartender not a waiter but an apparent couple last month sat on our patio, it wasn’t my table but I ended up clearing their first course before I dropped off their drinks and as I’m taking plates off the table from in front of the girl she lunges forward and loudly goes “are you f*****g someone else” I’m naturally kind of jumpy so I flinch a little and the guy says “wow you’re scaring her” to which the girl responds “are you F*****G anybody else?” I put the drinks down after clearing the table and very much tried not to overhear anything else.

#51

I saw a girl show up for a date on who knows what pills, and the guy she was seeing came there a lot with other regulars who all happened to be there that night. Not only was she strung out she showed up with her dog and her boss drove her there and was sitting with her. They sat outside on the patio and he was inside with his friends at the bar. I kept having to ask if the boss and the girl wanted any food until the boss finally ordered some food. She ends up eating a salad inside with the regular, and that was about the end of their interactions. Now back outside on the patio food is nearly up and she goes back outside and is sitting with the boss while falling out of her chair, and I dont know what was said as I was watching on from inside. She swings to slap the boss misses finds his phone and just spikes it on the concrete. I mosey on outside and ask if I should just pack the food to go and hes just replies like yeah that would probably be best. I doubt anything will ever top that level of f*ckery while I work there.

#52

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.

#53

This was a lifetime ago, but the guy was being pretentious, condescending, and boring. The girl was eye f*****g me the whole time. I ran into her a week later on campus and found out that was a first date that never got a second. She and I ended up dating for quite some time and had a couple bonus moments over the years when we both were single at the same time.

#54

One time waiting tables at Olive Garden we had a couple that came in and the guy proposed to his girlfriend. The girlfriends response was along the lines of ‘Are you kidding
me??? No!’ She then promptly left. Unless the OG has a significant meaning to your partner it’s not a good idea to do that.

#55

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.

#56

Not my table, I just happened to be at the right place at the right time. This pretty, well dressed woman was stumbling in my direction, so I moved forward to see if she needed directions to the bathroom. Before I could reach her, one of our attractive male managers walked out of the coat closet right as she was walking in front of it.

It all happened wicked fast. She kind of… stumbled into the closet and pulled him in with her, shutting the door. I didn’t know what to make of it so after a minute I went to investigate, opening the door at the same time as the bewildered manager was reaching for it, trying to show the now sniffling woman out.

She was pretty upset and intoxicated and he was trying to escape, but what he gathered was that she was on a date with her long term boyfriend. This was an expensive steakhouse and they were celebrating some kind of milestone so she was convinced he would propose. When it didn’t happen she stormed out, didn’t even tell the guy why she was upset. He was all kinds of confused too, until he went to go look for her when she didn’t come back to the table.

As a server you see a lot of bad dates, couples arguing, and instances of someone being stood up. This one stuck with me.

#57

It’s a long story, but I’ll try to make it short.

Worked at a Korean BBQ place in college (the kind where food is cooked on a grill at the table). Obvious first date comes in, guy immediately goes to hoarding the conversation. I give my spiel, he cuts me off, tells me he’s going to order and handle everything, and puts in a huge order. Go to the table to cook it up, and he insists he’ll do it. Notice he cooks the pork belly for all of 3 minutes- go ask him if he’s sure it’s done, he says “I like it this way”, and I say “yeah, but what about her?” And point to the date. She murmurs she likes it a little crispier, and he insists it’s better this way. I tell them it’s recommended to cook it longer to ensure it’s safe to eat. Leave to handle other tables.

Come back and he’s still yapping away, food literally spewing out of his mouth as he talks. Hands are covered with kimchi and meat juices. F*****g disgusting. Again, he goes to cook the chicken, and I notice it’s severely underdone. Tell my manager, who tells my owner (who is actually South Korean- I’m white, so I suppose I don’t look the part?)- he goes over and tell the customer he cannot let him eat the chicken that raw, it’s a hazard. They start arguing, and mid-argument, the girl just gets up and leaves. No goodbye or anything. The guy follows her out, and returns alone, looking sad/confused. But he sits down, and continues to house his entire order of severely undercooked Korean BBQ, before leaving in a hurry after he wrapped up. He tipped like the j*****s he was.

I can only assume his stomach immediately began to reject the undercooked meat, so he had to rush home to get sick. It was a spectacle, and I’m glad the girl got out of there without having ate any of the undercooked meat.

#58

Couple came in arguing about whether they should break up or not — then ordered separate meals and didn’t speak the entire time. Paid separately, too.

#59

Not a waiter but I worked a sushi bar. It’s a short, simple, sweet story. He & she were coworkers. He thought it was a date. She thought they were going out as friends. He was absolute s**t at keeping a conversation going. She was straight up bored.

I tried to help, jumped in and tried to give them topics to talk about whenever there was a lull in my work. He couldn’t do anything with what I gave him. I talked about Ghibli while he was in the bathroom. She was actually into it. We made plans to meet up at another bar at the end of my shift.

She didn’t show. Came in a week later, apologized, something came up. I said that’s cool, we should do something another time. I got laid off before I got her number.  😭.

#60

I was somewhere in between 2 or 3 months bartending on the side at a new joint and this sweet girl sat and asked for me to chill a bottle of champagne to surprise her boyfriend who was meeting her to celebrate their three-year anniversary. He showed up and was the guy I had broken up with 6 months previous. We only dated for 4 months probably but holy s**t. I acknowledged that I knew him but just generically and was just minimal contact as possible but it was super weird. I still feel horrible I didn’t know how to let her know somehow.

#61

A couple and their daughter come sit at my table. Daughter was maybe 16ish, the dude was kinda fat and ugly tbh, but the wife was HOT. Normal table except the wife was staring at me the entire time. Anywhere I’m walking around the restaurant, she’s looking. My coworkers are coming up to me asking if I’m aware of it as if it wasn’t painfully obvious. I’m trying to play it cool and act like
I don’t even notice bc I don’t want to p**s off the dad, but he doesn’t even seem to notice. After they’ve paid and left I go to grab the check and they left me a fat tip plus the dude left me his wife’s number w/ a note to text her, which is weird but no biggie, people have their kinks. But you guys brought your kid along come on. 

Never texted her bc that’s a can of worms I didn’t want to get involved with, but I did consider it bc the wife really was one of the most beautiful women I’ve ever seen .

#62

It didn’t so much go horribly, but as their server, I just kinda felt bad. My first job was at Steak and Ale, which apparently was a fairly nice place in the 70’s and 80’s. I got a job there in 2004, and by that point the quality was more like an Applebee’s or TGIF but with a salad bar.

Not gonna lie, it was a really fun job, and I loved it there. But sometimes we would get people come back for their 20th anniversary or so because they had proposed at a Steak and Ale all those years before, and it was a really special event for them.

I didn’t have the heart to tell them that the stained glass window four feet away from their table had a bullet hole in it. Or that even at 18 years old, my boyfriend and I celebrated our anniversary at a nicer place.

#63

Not a waiter, but ex-chef in an open kitchen. This one will probably get buried but…

Scene- Valentine’s Day…

Table- right next to the open pass, slap bang in the middle of the restaurant (so close we could hear the couple chatting), semi-circular booth around a round table, couple’s backs to the kitchen.
They both started off on the left hand side of the bench

During the dinner, man was unloading his feelings towards her- how amazing she was, blah, blah, blah.
She was constantly slowly edging around the booth, he followed.

By the time dessert rolled round woman was pretty much on the right hand side of the booth, he was still following her round.

His next words were, “and that’s why I’ve decided to ask you to marry me (shows the ring)”

Her, “are you f****n’ kidding me?!”

She immediately gets up, storms out the restaurant, he just sits there, not moving, not crying, literally sits there.
As soon as we as staff heard what she said and did, we dipped below the pass and gestured wtf?! To each other.

Anyway, he eventually got up and left, no one really acknowledged what had happened, he paid for everything and we never saw nor heard from him again!

The restaurant has been closed for a good few years now, but that one, that one was a night to remember for everyone involved.

#64

Not a waiter, but I once saw a guy try to impress his date by doing a magic trick with a bread roll… He accidentally flung it across the restaurant and it hit another couple’s wine glass. Pretty sure that was their last date.

#65

There’s a family on my son’s baseball team where the husband and wife were out to dinner for their anniversary and he choked to death on a piece of steak. She was a nurse and another restaurant patron was a doctor. Both tried desperately to help but he passed away – at dinner celebrating their anniversary. Had two young boys. Very, very sad and I still struggle with how traumatic it must have been.

#66

One patron asked me, the host, to tell his girlfriend that we had a rule that one person couldn’t eat all the loaded nachos. She called him out and ended it right there.

#67

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.

#68

Fancy steak restaurant- guy takes his girlfriend for a date, complains about his table being too close to a family with young kids so we move him. She breaks up with him and storms out JUST AFTER ORDERING. He asks for the bill, their waiter didn’t understand what was happening so brings the bill. He pays the bill then leaves crying. I still think he should have just stayed and tried to eat both meals, but then I’m a tight greedy b*****d!

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