Serving people drinks isn't as easy as it might seem. You need to memorize dozens of recipes, stay on your feet for long hours, multitask under pressure... and avoid melting into the floor from the cringe around you!
Recently, Reddit user Nojunkpeter asked bartenders on the platform to share the most awkward conversation they've overheard at work, and hundreds delivered. From painfully bad blind dates to impromptu financial interventions for spoiled kids, these unforgettable situations stuck with them for all the wrong reasons.
#1

Happened a long time ago but saw a man and a woman on what I assumed was a first date. About an hour after arrival she finished a drink and was shortly after completely unconscious.
When asked if she was ok, The man said she “must be tired” and said he was going to take her home. Realising she wasn’t waking, an ambulance was called followed by the police. He tried to make a prompt escape through the fire exit and was blocked by a member of staff.
She got taken away by the ambulance, him in the police car. Horrible to think what could have happened.
When asked if she was ok, The man said she “must be tired” and said he was going to take her home. Realising she wasn’t waking, an ambulance was called followed by the police. He tried to make a prompt escape through the fire exit and was blocked by a member of staff.
She got taken away by the ambulance, him in the police car. Horrible to think what could have happened.
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76points
#2

Not a bartender, but overheard a couple on a blind date realizing about 20 minutes in that they shared the same dad. He apparently had a secret second family two towns over. The absolute silence that followed was the loudest thing I've ever heard.
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58points
#3

In the late 90’s or early 00’s two lesbians came to the bar and ordered 2 shots each. They told me they needed the courage to come out to their families.
Later they sat at a large table and ordered a pitcher of margaritas for the table of 8 or 10 people. The conversation was flowing and filled with plenty of laughter until suddenly there was none.
I hope those women found peace with themselves without the need of approval from their family.
Later they sat at a large table and ordered a pitcher of margaritas for the table of 8 or 10 people. The conversation was flowing and filled with plenty of laughter until suddenly there was none.
I hope those women found peace with themselves without the need of approval from their family.
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55points
#4

A old Scottish guy asked me for 2 x Pina Coladas. So I went away, made them and brought them back and set them in front of him. He looked confused and angry when I was putting the little umbrellas and sparkly stick in the drink and asked him for the money.
Turns out he actually asked for 2 “pints of lager” in his thick Glaswegian accent! He was not impressed!
Turns out he actually asked for 2 “pints of lager” in his thick Glaswegian accent! He was not impressed!
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42points
#5

Not a bartender, but it’s a drinking story … heard while waiting at the DMV.
It’s the DMV, where social norms don’t seem to apply.
Disheveled guy in the waiting room picks up his mobile phone, calls a buddy in a loud voice and says “yeah, I got busted for a dui, so now I can’t use my CFL (commercial driver license) to drive trucks and lost my job doing that. But I’m at the DMV to apply for a school bus driving permit, so I’m gunna do that until my CDL is off suspension”.
All the folks of child rearing age froze, looked up, and exchanged incredulous glances with each other.
It’s the DMV, where social norms don’t seem to apply.
Disheveled guy in the waiting room picks up his mobile phone, calls a buddy in a loud voice and says “yeah, I got busted for a dui, so now I can’t use my CFL (commercial driver license) to drive trucks and lost my job doing that. But I’m at the DMV to apply for a school bus driving permit, so I’m gunna do that until my CDL is off suspension”.
All the folks of child rearing age froze, looked up, and exchanged incredulous glances with each other.
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41points
#6

Bartending at this corporate afternoon network function. Lady signals she wants another glass of wine…
Woman A: I really shouldn’t be drinking wine.
Woman B: (pointing to her tummy) because of the baby?
Woman A: I’M NOT PREGNANT! How dare you…
Woman A: I really shouldn’t be drinking wine.
Woman B: (pointing to her tummy) because of the baby?
Woman A: I’M NOT PREGNANT! How dare you…
40points
#7

The ex-wife and (adult) son of one of our regulars came in one time. They got pretty sloshed, and started slow dancing. Bear in mind nobody dances at this pub, it’s not that kind of vibe.
The vibe they gave off was unsettling, too romantic for mother and son. Everybody was uncomfortable. Then they started kissing. Not a polite little smooch of an adoring and tipsy mom on her beloved son, KISSING.
That’s when I busted it up, told them they needed to leave and zeroed their tab just to get them the hell out of there.
Everybody knew the guy whose ex and son they were. We all felt extra extra uncomfortable because we knew him. It was, hands down, the ickiest thing I’ve ever witnessed.
I don’t know if anyone told our regular (and friend) but I didn’t. Jesus how do you even broach that topic. I kind of assumed he knew at least something was amiss there, and it might have been a cause of their divorce. Anyway frick that, I’m not touching that with a ten foot pole.
EWWW.
Info: Some commenters were assuming step-mom. No, it was mother-son, biological.
The vibe they gave off was unsettling, too romantic for mother and son. Everybody was uncomfortable. Then they started kissing. Not a polite little smooch of an adoring and tipsy mom on her beloved son, KISSING.
That’s when I busted it up, told them they needed to leave and zeroed their tab just to get them the hell out of there.
Everybody knew the guy whose ex and son they were. We all felt extra extra uncomfortable because we knew him. It was, hands down, the ickiest thing I’ve ever witnessed.
I don’t know if anyone told our regular (and friend) but I didn’t. Jesus how do you even broach that topic. I kind of assumed he knew at least something was amiss there, and it might have been a cause of their divorce. Anyway frick that, I’m not touching that with a ten foot pole.
EWWW.
Info: Some commenters were assuming step-mom. No, it was mother-son, biological.
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39points
#8

A couple both admitted to cheating. Turns out both cheated with the same dude.
It was all I could do to make up busy - work near them to be able to hear it all play out.
It was all I could do to make up busy - work near them to be able to hear it all play out.
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36points
#9

I was a waiter but I was working behind a diner counter a lot of the time. Close enough to a bar? I have two awkward stories I'll never forget:
-Guy who brought a script along to a first date and made his reluctant date run lines with him (he was not very good), then talked for far too long about the nuances of his great performance while the date sat there silently nodding. Sir do you think this is a flex
-Pair of teens, one of them was sobbing over being dumped. Her friend said "don't cry you're too hot to be sad!" and tried to kiss her while she leaned away in horror and disgust. My skin crawls with secondhand embarrassment whenever I think about it. Sir....
-Guy who brought a script along to a first date and made his reluctant date run lines with him (he was not very good), then talked for far too long about the nuances of his great performance while the date sat there silently nodding. Sir do you think this is a flex
-Pair of teens, one of them was sobbing over being dumped. Her friend said "don't cry you're too hot to be sad!" and tried to kiss her while she leaned away in horror and disgust. My skin crawls with secondhand embarrassment whenever I think about it. Sir....
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34points
#10

I'm a bartender, but would help serve tables during slow periods when there weren't many servers on.
Man comes into the dining room waiting on another person.
She arrives shortly after, sets her purse and a manila envelope down and goes to the washroom. I drop off an little amuse bouche which was pureed watermelon juice while she was gone and explained what it was to the man.
Lady comes back, and maybe 30 seconds later I hear raised voices, I return just in time to see her bolt back to the bathroom while digging in her purse. She returns minutes later, looking very upset and unwell. More angry talking, papers being handed over a couple times, then she grabs her stuff and moves to the bar, still flipping through papers and signing things.
I ask if I can help, and she barks "no, you're great, not your fault at all. But we're here to sign divorce papers and he didn't tell me the juice you dropped off was watermelon. I'm allergic to watermelon".
I understood her on a cellular level at that moment.
Man comes into the dining room waiting on another person.
She arrives shortly after, sets her purse and a manila envelope down and goes to the washroom. I drop off an little amuse bouche which was pureed watermelon juice while she was gone and explained what it was to the man.
Lady comes back, and maybe 30 seconds later I hear raised voices, I return just in time to see her bolt back to the bathroom while digging in her purse. She returns minutes later, looking very upset and unwell. More angry talking, papers being handed over a couple times, then she grabs her stuff and moves to the bar, still flipping through papers and signing things.
I ask if I can help, and she barks "no, you're great, not your fault at all. But we're here to sign divorce papers and he didn't tell me the juice you dropped off was watermelon. I'm allergic to watermelon".
I understood her on a cellular level at that moment.
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31points
#11

Not too long ago, I had to stay a few nights at a local hotel for a work event. It just so happens my wife is a bartender at one of bars at that hotel. I was psyched to have a few drinks at my wife's bar without the pressure of having showed up specifically to hang with her.
After work, me, a colleague, and HIS wife went down to have a few drinks. Within an hour or two, we're all relatively drunk and jovial. A well put together lady in her early sixties was sitting on the far end of the group, next to my colleague's wife.
My buddy and I are sharing some fun industry stories with his wife which were all 100% innocuous and completely tame. Suddenly, the lady leans over to my friend's wife and says "I'm so sorry, but did I hear you say you're a hotwife?"
Important to note that my friend and his wife are classic strait laced, slightly innocent southerners, and the word "hotwife" was definitely never mentioned. She looks at the older lady and says "I'm sorry, but I don't know what that means." I DO know what that means, and I'm now laser focused on this conversation.
To my surprise, the older lady straight up says "Oh. It means I'm a married woman, and me and my husband like to have intercourse with other people. Do you three like to do that?"
At this point, my buddy's wife is beat red and just stammers out "Oh...no. I'm sorry, I don't think so." Without missing a beat, the older lady is like "well I heard you mention you two are married." Then she gestures to me and my colleague, and says "and those two are clearly together, so I figured all three of you were fair game." Me and my colleague are NOT romantically involved, but I couldn't help but feel like that was meant as a compliment.
At this point, my friend's wife is completely frazzled and is like "oh no....he's (me) married to the bartender". This old fox lights up like, "oh darn, I'm getting the bartender too!"
She stammers out a few more apologies to the older lady, who polishes off her beer and cheerily says "oh no worries. Sometimes in this lifestyle ya gotta take risks! Have a good night!" Then she closes her tab and disappears.
The next morning I woke up with a note in my phone that says "that older lady tried to do all three of us" (as if I could ever forget). Later, my wife told me her and the other bartender heard every word and were laughing their bums off the entire time.
After work, me, a colleague, and HIS wife went down to have a few drinks. Within an hour or two, we're all relatively drunk and jovial. A well put together lady in her early sixties was sitting on the far end of the group, next to my colleague's wife.
My buddy and I are sharing some fun industry stories with his wife which were all 100% innocuous and completely tame. Suddenly, the lady leans over to my friend's wife and says "I'm so sorry, but did I hear you say you're a hotwife?"
Important to note that my friend and his wife are classic strait laced, slightly innocent southerners, and the word "hotwife" was definitely never mentioned. She looks at the older lady and says "I'm sorry, but I don't know what that means." I DO know what that means, and I'm now laser focused on this conversation.
To my surprise, the older lady straight up says "Oh. It means I'm a married woman, and me and my husband like to have intercourse with other people. Do you three like to do that?"
At this point, my buddy's wife is beat red and just stammers out "Oh...no. I'm sorry, I don't think so." Without missing a beat, the older lady is like "well I heard you mention you two are married." Then she gestures to me and my colleague, and says "and those two are clearly together, so I figured all three of you were fair game." Me and my colleague are NOT romantically involved, but I couldn't help but feel like that was meant as a compliment.
At this point, my friend's wife is completely frazzled and is like "oh no....he's (me) married to the bartender". This old fox lights up like, "oh darn, I'm getting the bartender too!"
She stammers out a few more apologies to the older lady, who polishes off her beer and cheerily says "oh no worries. Sometimes in this lifestyle ya gotta take risks! Have a good night!" Then she closes her tab and disappears.
The next morning I woke up with a note in my phone that says "that older lady tried to do all three of us" (as if I could ever forget). Later, my wife told me her and the other bartender heard every word and were laughing their bums off the entire time.
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31points
#12

Not a bartender but just wanted to give a shout out to a bartender that asked me if I was OK because I was by myself, surrounded by people. Just told her I was here for work and I liked the noise but didnt feel like talking to anybody. I liked talking to her though, at least she was nice.
Anyways, bartenders are good people.
Anyways, bartenders are good people.
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29points
#13

Blind date. Guy arrives first and lets me know about the situation. They were paired together on some paid matchmaking dating app. He’s dressed nice, probably in his late 30s and is friendly enough, but clearly focused on prepping for the date.
It’s 5:45pm and she’s supposed to get there by 6:00pm. Well, 6:15 pm rolls around and he flags me down.
“Um I guess can I order a glass of wine? And maybe a cheese board?”
I kind of gloss over the fact that his date is still not there and just take his order, trying to keep things light and not stress him out. Before I leave he goes, “You know what. I’ll just take the whole bottle.”
So I come back with the bottle of wine, and the cheese board comes out pretty quickly. It’s now around 6:25 PM and there’s still no sign of her.
“Man. I’ve tried texting and calling the dating service since I don’t have her direct number. But they’re not answering. Looks like I’m being stood up.”
Sure enough, in walks a very attractive woman in her late 30s, and she looks PISSED. She comes up right to the bar, “Um yeah hi I’m supposed to meet a date here? Is there a Mike here?”
“Oh! Whitney? Hi I’m Mike! It’s nice to meet you,” has he stands up out of his chair, ready to greet her with seemed to be the beginning of a hug.
Leaning on one tapping foot with folded arms the woman says, “How was I supposed to know you were inside the restaurant?! I’ve been waiting outside for you for thirty minutes. Oh and it looks like you’ve already helped yourself to dinner. Good start.”
I could hear a pin drop. I heel turned away and pretended to clean some glassware while this guy just kind of stood in shock.
“Um. I’m sorry about that. Well, would you still like to join me?”
“Ugh I GUESS, I’m starving.” And she plops down at the bar and starts picking at the cheese board.
“Well, I got a bottle of Pinot Noir, would you like a glass?”
“Why would you think I like wine? You ordered for me without asking? That’s rude.”
“…..you don’t have to have a glass. I was just offering since there’s a bottle on the table. You can order whatever you’d like”
This woman, rolls her eyes and without bothering to look in my direction says, “Grey goose dirty martini with stuffed blue olives.”
This was my moment to shine. In the plainest, flattest affect with the enthusiasm of a piece of cardboard I snapped back, “No stuffed olives. No Grey Goose.”
Me and her had a bit of a stare down, she’s not saying anything as I see the gears turning in her evil stupid little head, until the guy finally says, “You know what. She can pay for her drink, and I’m going to move down there,” as he gestures to the end of the bar, “This doesn’t seem to be going well. I hope you have a nice night. Best of luck.”
And he picks up his glass of wine and moves to the end of the bar.
CAN I TELL YOU the satisfaction I had to pick up this guys cheese board and bottle of wine, with the best little grin on my face while I moved the order away from her, ugh. I still think about it to this day.
The woman goes, “WOW really? You make me wait outside and THEN bail? What a man. I wasn’t interested in you from the beginning. HAH!”
I can tell she’s waiting for a response or some engagement, but the guy gives he nothing.
She stands there again, looking stupid as hell, and goes “Really? REALLY?” So I go over to her and ask, “We do have Tito’s. Would you like a Tito’s Martini?” And she scoffed and walks out.
It’s 5:45pm and she’s supposed to get there by 6:00pm. Well, 6:15 pm rolls around and he flags me down.
“Um I guess can I order a glass of wine? And maybe a cheese board?”
I kind of gloss over the fact that his date is still not there and just take his order, trying to keep things light and not stress him out. Before I leave he goes, “You know what. I’ll just take the whole bottle.”
So I come back with the bottle of wine, and the cheese board comes out pretty quickly. It’s now around 6:25 PM and there’s still no sign of her.
“Man. I’ve tried texting and calling the dating service since I don’t have her direct number. But they’re not answering. Looks like I’m being stood up.”
Sure enough, in walks a very attractive woman in her late 30s, and she looks PISSED. She comes up right to the bar, “Um yeah hi I’m supposed to meet a date here? Is there a Mike here?”
“Oh! Whitney? Hi I’m Mike! It’s nice to meet you,” has he stands up out of his chair, ready to greet her with seemed to be the beginning of a hug.
Leaning on one tapping foot with folded arms the woman says, “How was I supposed to know you were inside the restaurant?! I’ve been waiting outside for you for thirty minutes. Oh and it looks like you’ve already helped yourself to dinner. Good start.”
I could hear a pin drop. I heel turned away and pretended to clean some glassware while this guy just kind of stood in shock.
“Um. I’m sorry about that. Well, would you still like to join me?”
“Ugh I GUESS, I’m starving.” And she plops down at the bar and starts picking at the cheese board.
“Well, I got a bottle of Pinot Noir, would you like a glass?”
“Why would you think I like wine? You ordered for me without asking? That’s rude.”
“…..you don’t have to have a glass. I was just offering since there’s a bottle on the table. You can order whatever you’d like”
This woman, rolls her eyes and without bothering to look in my direction says, “Grey goose dirty martini with stuffed blue olives.”
This was my moment to shine. In the plainest, flattest affect with the enthusiasm of a piece of cardboard I snapped back, “No stuffed olives. No Grey Goose.”
Me and her had a bit of a stare down, she’s not saying anything as I see the gears turning in her evil stupid little head, until the guy finally says, “You know what. She can pay for her drink, and I’m going to move down there,” as he gestures to the end of the bar, “This doesn’t seem to be going well. I hope you have a nice night. Best of luck.”
And he picks up his glass of wine and moves to the end of the bar.
CAN I TELL YOU the satisfaction I had to pick up this guys cheese board and bottle of wine, with the best little grin on my face while I moved the order away from her, ugh. I still think about it to this day.
The woman goes, “WOW really? You make me wait outside and THEN bail? What a man. I wasn’t interested in you from the beginning. HAH!”
I can tell she’s waiting for a response or some engagement, but the guy gives he nothing.
She stands there again, looking stupid as hell, and goes “Really? REALLY?” So I go over to her and ask, “We do have Tito’s. Would you like a Tito’s Martini?” And she scoffed and walks out.
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27points
#14

Two ladies with Northern U.S. or Canadian accents. I heard "Yeah sure, you can get rid of a body in a woodchipper. You just gotta Freeze it real good first".
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27points
#15

These kids (probably around 12 years old) on their first date. The boys mom brought them to the restaurant and planned on sitting at the bar to give them alone time.
The boy wouldn't let her leave the table. The girl and the mom kept hinting at how fun it would for them to be alone and how the mom probably didn't want to sit there during the date. The mom tried to leave and the boy literally grabbed her by the hand and wouldn't let go.
Having your mom be the 3rd wheel on your date was just as awkward as it sounds. The mom came back and became kind of a regular because she liked the food. She told me the girl dumped him after that and it wasn't pretty.
The boy wouldn't let her leave the table. The girl and the mom kept hinting at how fun it would for them to be alone and how the mom probably didn't want to sit there during the date. The mom tried to leave and the boy literally grabbed her by the hand and wouldn't let go.
Having your mom be the 3rd wheel on your date was just as awkward as it sounds. The mom came back and became kind of a regular because she liked the food. She told me the girl dumped him after that and it wasn't pretty.
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27points
#16

My most awkward was sad.
One of the men only had a couple months left to live. Had aggressive cancer. Super awkward as a bartender. Wanted the dude to have a good time, would have given him free drinks, but I assume that wouldn't have been good for him either. You want to be friendly and fun but the vibe was just sad and humble. You don't want seem like your being a pity party either. They are out trying to enjoy the last of their time, but it was a sad last bro hurrah. But as your out celebrating your passing friends life, the interactions all seemed awkward. I forgot to ring up a bunch of their drinks. I really didn't know how to interact with a group. So I was just friendly.
Hope the dude had a good run. Seemed like a super nice guy.
One of the men only had a couple months left to live. Had aggressive cancer. Super awkward as a bartender. Wanted the dude to have a good time, would have given him free drinks, but I assume that wouldn't have been good for him either. You want to be friendly and fun but the vibe was just sad and humble. You don't want seem like your being a pity party either. They are out trying to enjoy the last of their time, but it was a sad last bro hurrah. But as your out celebrating your passing friends life, the interactions all seemed awkward. I forgot to ring up a bunch of their drinks. I really didn't know how to interact with a group. So I was just friendly.
Hope the dude had a good run. Seemed like a super nice guy.
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24points
#17

Christmas Eve, couple sat at the bar just slowly realizing over about 90 minutes that they should just get a divorce. Sad, not angry. Absolute nightmare to navigate and work around.
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23points
#18

Not a bartender anymore but I will never forget overhearing a pretty attractive woman explaining to her friend that she stopped dating and just has intercourse with her brother. She said this with a straight face and kept explaining how much less stressful it is than dating. The other girl mentioned that she wished she had a brother so she didn’t have to worry about dating.
I have two sisters and could barely hold it together. The other bartender and I thought she was trolling. The tone of normalcy and relief in the conversation was almost as unsettling as the topic of discussion itself.
I have two sisters and could barely hold it together. The other bartender and I thought she was trolling. The tone of normalcy and relief in the conversation was almost as unsettling as the topic of discussion itself.
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23points
#19

Guy lamenting how hes the Boss in the house, when she honked outside to pick him up and he nearly jumped of the chair, tipped way to high bc couldn't wait for change and stormed out of my pub.
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22points
#20

Two of our regulars were a couple that were generally known to be swingers. They were harmless and a lot of fun.
One evening, as a couple, they started hitting on our new barback. He was young and naive so everything kept going over his head. Eventually, the couple got so flabbergasted that the husband just kinda shouted, “Do you want to do my wife?”
The barback thought he was being accused of something so he mumbled a quick, “No, no, no. Sorry. I’m just friendly. Sorry.”.
One evening, as a couple, they started hitting on our new barback. He was young and naive so everything kept going over his head. Eventually, the couple got so flabbergasted that the husband just kinda shouted, “Do you want to do my wife?”
The barback thought he was being accused of something so he mumbled a quick, “No, no, no. Sorry. I’m just friendly. Sorry.”.
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21points


