These bartenders retell the cringy flirting they've seen while on the clock.
She Obviously Wanted Nothing To Do With Them
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“A couple college guys were hitting on this fiery Irish redhead who clearly wanted nothing to do with them. She ended up going to the jukebox to get away from them, and ended up picking a couple rock songs and sat down somewhere else.
The guys thought it would be a great idea to go to the jukebox, look her in the eyes and pay extra to have their song (I believe it was ‘Sexy And I Know It’) start immediately playing. She almost started a bar fight with them. I don’t think that was what they were going for.”
He Was Such A Gym Rat
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“At a CrossFit Christmas party being held at the local sports bar known for douchey patrons, I got to witness a spectacularly drunk CrossFit enthusiast hit on a girl with the amazing pickup line of ‘So, lemme tell you about my workout,’ followed by full-on flex-grunting (to show his arms), and lifting his shirt to show her his flabby stomach, while asking her if she wanted to feel his abs.
She immediately latched on to one of the equally awful but more ripped partygoers. Flex-Boy didn’t notice that she’d left and kept staring at his ‘abs’ while telling the no-longer-there girl about his ‘workout’ before he looked up and noticed that she was gone. Dude was a bad gym meme come to life.”
What Just Happened?
“I was bartending at an anime convention in Chicago. A girl cosplaying some character is sitting down taking a break. A fat scruffy guy walks up and sits down next to her. He asks her if she has any STDs.
She says no, and they both get up and leave together.”
They Went Through A Massive Flux Of Emotion
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“I once bartended at a club for a college function. Rich kids, mostly. I had a couple parked at the end of my bar, both freshly 21. I don’t think they were actually a couple to start, they came separately and spent the first hour or so in awkward small talk. Then out of nowhere, they started sucking face. It was like they’d never done it before, and they both had their butts on the stools leaning over really really far to get to each other. It was weird to watch. It was still better than when they decided to make out on top of the bar though, which of course was short lived.
I thought it would end there, but after almost another hour of on-again-off-again making out and of course, more tequila shots, the girl randomly starts SOBBING. I thought they were fighting, but then the kid takes her face in his hands and starts bumping his forehead against hers. As if it was going to comfort her? And then HE STARTS SOBBING. I didn’t get to see how it ended, but they were gone by last call, physically, mentally and emotionally.”
He Was Utterly Disgusted
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“I got to the bar early for my shift. I killed time by playing pool with my brother, who was the head cook. We finished our last game, and on my way to the bar I got stopped by a younger married couple, who were pretty wasted, that was leaving.
The woman grabbed my arm and in her wasted state of mind goes, ‘Oh my God!!! You look like that guy from Zac Brown band, what his name? Uh…’
I came in with, ‘Zac Brown?’ I get it all the time (except I’m ginger?) with my majestic beard and sock hat.
She asked if we could take a picture and handed her husband the phone. Right before he took the picture, she turned to me, and licked my beard! From my jawline all the way to my hairline. The look on my face, in the picture, was of complete and utter disgust. She thanked me and left.”
This Conversation Went Off The Rails, Quickly
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“I bartend at a chain restaurant, most known for their stupid promotion of fried foods for cheap… Anyway, I’ve been there for about five years. I’ve seen a lot of stuff, but this one always stands out. One night there was a couple, a man and a woman, who were just hanging out enjoying a drink.
I always ask the question, ‘So what do you have going on tonight?’ to get the conversation rolling.
The guy says, ‘I’m trying to go to pound town!’
Confused, I ask, ‘Dang, well since I don’t know you both, who’s this lovely lady you’re sitting next to?’
He responds, ‘Oh, this is my wife.’
I laughed, and said, ‘Dude, do you have to try that hard with her?’
Him: ‘No way man, we are swingers. She’s looking for some mischief, too.’
Stunned, I said ‘Wow, cool…good luck.’
Dude says ‘You got a girlfriend?’
(At the time I did) ‘Yeah…’
Him: ‘Can I see a picture of her?’
Me: ‘No.’
Him: ‘Aw c’mon dude! Hey, check this out!’
He promptly shows me a picture of his wife, butt naked, in a suggestive pose.
Me: ‘Wow man, lucky you.’
Him: ‘You wanna fool around with her, and I’ll fool around with your girlfriend?’
Me: ‘Here’s your tab, get out of here.’
He Was So Out Of His League
“I’ve bartended on and off for about 12 years, and a few weeks ago I saw the absolute worst encounter of my career.
A lady came in and sat down. She was a drop dead gorgeous redhead whose ID said 41 years old, but I would have guessed 28 to 32 years old. We chatted for a bit and she told me she was here to meet a blind date she had found using eHarmony. After a little while, I noticed she was still alone and was already thinking about how this poor guy was about to miss out on a golden opportunity, and then he showed up, out of breath, sweaty, and looking like Milton from ‘Office Space.’ He waddled up to her at the bar, introduced himself, and said, ‘I thought you said you were gonna dress up?’ Needless to say, the date didn’t last long.”
The Things You Overhear
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“You get used to hearing the middle of people’s conversations as a bartender or waiter. It’s fun sometimes. Sometimes a trashed, middle-aged woman clearly on a blind date with a guy with a ponytail says things like, ‘…and I’ve never been more humiliated and turned on at the same time.'”
The Whipped Cream Caper
“I bartended through college. One Saturday I was working an early shift at the bar, and a family of drunk rednecks came in. There was one college-age girl and two college-age guys. All three were cousins. I like everyone, so I started talking to them.
The girl gets it in her head that I should eat whipped cream off her chest and take a shot with her. She was fairly attractive, but I politely declined. She became very insistent and started calling me gay. At this point, her cousins start exclaiming that if they weren’t related, they would be jumping at the chance. I got the feeling that if we weren’t in public, they would be jumping at the chance.
They will not let it go. At some point, I got really frustrated. I grabbed the whipped cream and walked over, she pulls out the front of her shirt, and I fill it with pretty much the whole can of whipped cream. She must have thought she was in for the motorboat of her life, but I just walked away and didn’t say anything. She closed up her shirt over top of the whipped cream and they left. It was super awkward. I still feel kind of bad about it.”
“Light ‘Em Up!”
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“I worked as a bartender when I was younger. I loved it, but it turns you off to booze. And you see some seriously nasty stuff like fights and people vomiting in potted plants and the like. There was another person who used to poop in a beer glass and put it in a toilet. They would then flush the toilet until it broke, and the staff had to clean everything up. That despicable woman was never caught, but I digress.
One night, a pudgy middle-aged man came to the club, and he was pretty much on the hunt for a lady. He was nice enough at the start of the night, but he became more belligerent as he got more and more wasted. He started hurling insults at staff who wouldn’t serve him quick enough, yelling, ‘Don’t you know who I am?’ I had no idea who he was, but he looked like the kind of guy who’d die of a heart attack in an alley shortly after romping around with a corner girl.
At about 2 a.m., he was at the bar flirting with a girl half his age, throwing money around and buying her expensive drinks. She was all over him, hands down his pants, licking his ear and letting him feel her up. He then asked for a bunch of shots, so I lined them up in front of his sweaty, gargantuan face. He then said, ‘Go on, light ’em up, mate!’ I refused because, you know, fire.
He got angrier and angrier until I thought he’d pop a valve right then and there so I said, ‘Look, I’m going to turn my back and if you light them up and I don’t see it, then that’s okay.’ He grinned and pulled a lighter out of his back pocket, so I turned around.
Luckily for me, we had mirrors at the back of the bar, so I saw the whole thing. He lit the first shot, kissed his lecherous trophy-lady on the cheek and said, ‘Up ya bum!’ and slammed the whole shot down, flames and all. Of course, that’s what was supposed to happen.
What actually occurred was a large, flaming shot being poured onto his face and the ample bosom of the drunk harpy standing next to him. VOOMP! It all happened in slow motion. Blue flames licked his face and hair and the girl’s chest. The busboy standing next to me had a bucket of water (I had hoped he’d just cleaned the toilets, but alas, no) and he tipped it over both of them. The flames went out and there was silence for a few seconds. Then he looked at his shirt and screamed, ‘Ya ruined my best shirt,’ and launched over the bar at the busboy.
A scuffle ensued during which I noticed his face swelling and generally pulsating like a slightly rotten tomato. The bouncers carried him out, and we took the girl into a back room so she could put some ice on her chest. He lurked outside for a while, apparently waiting for his newfound lover. We told him to go to the hospital, but he gave us the finger and told us to mind our own business.”
A Major Miscommunication
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“There was an old wasted guy not catching on that the hot young girl talking to him was a woman of the night. The woman did not realize that he didn’t know. He was actually thinking she was interested in him.
Meanwhile, the whole situation is clear as day to me and other patrons around them, but these two are just fumbling through the conversation, completely unaware that they were both misunderstanding one another. Pretty sad, but hilarious.”
“I Can Only Appreciate His Tenacity”
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“I saw a guy walk up to a girl and she slapped him. He immediately repeated the same thing to her friend and got slapped again.
He went down the line, and girls turned away, slapped him, or threw a drink in his face. No pause from one girl to the next. After a dozen, he got bounced. I never found out what he was asking, and so I can only appreciate his tenacity.”
So Cringey
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“I used to work at a bar when I was at university. I remember at the end of one night a guy had been hitting on a girl all night who was just dragging him along for expensive drinks, and then just turned in the spot, didn’t say thanks or anything and disappeared into the night.
He cried.”
Oh, Honey
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“A 300-pound sloppy blonde chick at a bachelorette party was aggressively hitting on one of my regulars. She was wearing a tank top at least two sizes too small and a crown with little man parts all over it.
My regular, albeit a very attractive man, is also very gay. He was too shy to say anything and tried to be nice because he understood that she was blitzed.
She grabbed his face and slobbered up his neck and face and tried to grab his crotch under the bar multiple times.”
“I Still Have No Idea What Was Happening There”
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“I was delivering some appetizers to a couple at the bar and caught a small snippet of their conversation as I dropped off the food.
Woman: ‘Remind me later, I have to clean the windows at home.’
Man: ‘Baby, I’d love to clean your windows real good.’
They then leaned over to kiss but missed each other’s mouths. The girl just sort of sucked on his chin for a second, before they realized they had food. I still have no idea what was happening there.”
He Got What He Deserved
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“I was a new bartender at a bar in a nice, suburban area. This girl who had a curvy but extremely sexy pin-up kinda vibe going (tats, pale skin, red lipstick, etc.) was getting hit on by this overweight dude who worked at a local cell phone store. He was overcompensating, trying to be a big shot. He buys a round of vegas bombs for the group they are with, like six or seven shots total. Not cheap shots. The tab for the round was more than $70. He puts it on his card and tips like a dollar. Not cool.
Fast forward five minutes, the bar staff really doesn’t like him now, yet this awful guy is still doing okay with this hot girl. In conversation with her, tipping comes up, and she asks how he tipped us. I told her the truth. A look just short of pure hatred erupts in her eyes. Turns out, she’s a server.
She stands up, pays for the drinks this guy was going to buy for her, and points across the U-shaped bar to a handsome guy, and says, ‘I’d like to buy him a drink.’ She walks over, sits next to him in plain view of the guy who was hitting on her before, flirts with him for an hour, and leaves with him. The butthurt look on his face was so satisfying.
The handsome guy was back in the bar a few weeks later, I asked him how it went. He said she ended up being crazy, but I didn’t care. That night, she was my hero.”
An Awkward Stare
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“On Halloween night, this man was flirting away with a very good looking policewoman (costume), and when it came to their turn to be served by me, he turns (I’m a dude, but was dressed up as a woman) and I ask them what their poison is.
She wanted a West Coast Cooler or something but the man just stared at me. So I stared back. Thus ensues a staring contest. Officer Fine was still standing there in stitches that I was ignoring the bar to stare this man down, then he says, ‘What’s your name?’
I give him my name while maintaining eye contact. He then says, ‘I find you strangely and incredibly attractive.’
My reply? ‘A water for the gentleman.'”
The YES Game
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“I once had this couple who had just gotten engaged come in and sit at my bar.
When the guy gets up and goes to the restroom, the woman tells me of a game they’re playing. The ‘yes’ game. They have to say yes to every question they are asked. She then tells me she wants me to have another male employee approach them in a few minutes and ask if they would like to come fool around with him, as a joke.
Guy gets back, I ask if they would like another round, and he asks for the tab. The girl looks at him, and he says okay, we’ll take another round.
Minutes later, a guy I work with approaches them and compliments them, focusing on him. I can tell the guy is feeling very awkward. He says to them, ‘This is going to sound strange, but would you two like to come back to my place and fool around?’
Without any hesitation, the guy yells ‘YES’ with the most excited look on his face. The look on the girl’s face was indescribable.
I wonder if they ever got hitched.”
He Was Such A Creep
“I wasn’t actually an official bartender at the time, but I’d made friends with the guys and was helping around since I decided not to drink that night.
A group of us (guys and girls) were on holiday on a friend’s yacht, let’s call him Nigel. Until that holiday, Nigel seemed like a normal guy, maybe a bit desperate with girls, but he just likes getting with girls. This is until we realized he’s actually a super creep with girls, like not just persistent, but aggressive to anyone seen hitting on ‘his girls’.
Mind you, all the girls he invited on the boat were ones he was actively trying to fool around with, including my ex. He’s also a rich brat that loves to throw his monetary weight around.
He takes us out in Barcelona to a few bars, and we settle down at one we’d been going to for the last few days. I was friends with the bartenders at this point, and I offered to help behind the bar.
Nigel proceeds to drop €50 immediately on shots, about three for every girl and watches them do them. He only orders shots with explicitly innuendo names, winking at them every time he orders.
Nigel keeps buying shots, they keep drinking. He then sees one girl walk off and dance with a guy. He’s instantly angry at her and tells her to book a flight home because she’s a brat. This happens two more times.
Eventually, he puts his arm around one of the girl’s necks and just lurches for her, tongue on display for all of us to watch with horrified enjoyment. She turns quickly, and he effectively licks her ear. He is then dismayed, orders three shots for himself, and tries to play it off. He keeps reminding the girls of how much money they now owe him or they can repay him for the shots in other ways.
The best thing about this was I got to watch this miserable mating attempt again and again for three weeks whilst on the boat. Things like this happened repetitively. Not to mention the whole drama that his ex and I are friends and he thinks I’m fucking her. Little does he know the reason we’re good friends is that I came out to her.
All in all, it’s a shame because if it wasn’t for his obsession with girls he’d probably be a good bloke.”
It Was So Awkward And Sad
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“I was bartending and my mother was at the bar. This guy who all the regulars stay away from, and only really tolerate because of how weird he comes in. He basically spent two hours asking people, including my mom, for advice on how to improve his online dating profile.
The women were all giving him dating advice while trying really hard to go back to the conversations they were having before he butted in. I felt bad for the guy because he was clearly really sad and lonely, but it was probably one of the most awkward experience I’ve ever encountered.”
