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40 Bartenders Reveal The Worst First Dates They’ve Seen That Range From Cringe To Heartbreaking
Relationships,CouplesMAY 27, 2024

40 Bartenders Reveal The Worst First Dates They’ve Seen That Range From Cringe To Heartbreaking

Ieva P.
Miglė Miliūtė
Ieva P. and Miglė Miliūtė
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Going on a first date can be exciting. You’re getting ready wondering how the night is going to go, and whether or not you will hit it off; and while many couples do, others - not so much.
It’s no surprise that bartenders are the people who get to witness many first dates—both good and bad. So when the redditor ‘gilesvg’ addressed the bartenders in the ‘Ask Reddit’ community, asking them to share stories of first dates going sour, they had plenty. If you’re curious about the fairytales that ended before they even began, too, scroll down to find them on the list below.
Below you will also find Bored Panda’s interview with a certified love life strategist, dating and relationship expert, Lisa Concepcion, who was kind enough to answer a few of our questions about how important first dates are.

#1

40 Bartenders Reveal The Worst First Dates They’ve Seen That Range From Cringe To Heartbreaking
Witnessed a high school reconnection/date where the girl showed up before him, dressed to the nines and obviously still infatuated with the idea of the football star. He shows up in a wife beater and a ball cap, scruffy/balding and not at all dressed for a date. Now its not a five star restaurant but a decent beach bar. She seems a bit put out but the date stumbles along. 
I can't help but hover as things go from awkward reintroductions to attempts at conversation. She's trying desperately to convince herself this date is a good idea and he's a great guy and it's obvious he's not. 
He's oblivious. Going on and on about how she'd make a great mom because she's a teacher. She replies joking "oh no, I love the kids but I get to give them back at the end of the day" etc and he doubles down. She changes the subject to fishing, he says she can't really enjoy fishing. She repeats herself and shares a story about fishing with her dad. He repeats its a man's hobby and she can't possibly actually find it fun. It just goes on like this and I can see she's getting more and more upset. 
At one point, he leans over and says something into her ear. Her face contorts in disgust. She says something like "that's how you think this date is going?"
He goes to the bathroom (still oblivious, this man, gotta hand it to him), she takes her chance and waves me over. 
"Two shots of fireball and the check, please." 
I shoot over to her, shots in hand. She knocks them back one after the other and I start giggling. 
"Can I just say something?" She nods. "This is in no way my business, but you seem really sweet and are way out of his league." She looks at me in shock and says "really?" 
"Yes. 100%"
She decided to pay the whole tab and jetted off before he got back. He looked at me and the empty seats and tried to hand me cash, I waved him off saying she had already paid. His utter confusion was so precious. It's still my favorite awkward first date story. So uneventful but just -chefs kiss-.
Great_Kitchen_371, Andrea Piacquadio/pexels
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226points

#2

40 Bartenders Reveal The Worst First Dates They’ve Seen That Range From Cringe To Heartbreaking
Not a bartender but saw a dude at the theater I used to work at. He was dressed up and had flowers for Valentine’s Day. He sat in the lobby for over an hour and quietly came up to the counter and asked if he could return his tickets.
IceFireHawk, Hatice Bara/pexels
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191points

#3

40 Bartenders Reveal The Worst First Dates They’ve Seen That Range From Cringe To Heartbreaking
Not witnessed but heard girl and guy go on blind date. They've been talking on phone before to get to know each other and here comes first Date. Met at a bar. He was there first waiting and she came in. They talk for minute and he says "oh let me get the flowers I got you. It's in the car" he walks out and doesn't return. Felt bad for her. You can at least finish date or drink and then gracefully leave.
Wesmom2021, cottonbro studio/pexels
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173points

“The first date is all about the first impression,” the dating and relationship expert Lisa Concepcion told Bored Panda, discussing the importance of a first date. “This is when we are evaluating if the other person is a match to us. If a person is rude, distracted, lacks manners, isn't presentable and seems disheveled, it will impact our decision as to whether or not we choose to see them again.”

#4

40 Bartenders Reveal The Worst First Dates They’ve Seen That Range From Cringe To Heartbreaking
A young couple, no more than twenty. He ordered for her (red flag #1). What he ordered for her was a salad (red flag #2, and a nice big "oof" to pair with it). He ordered a standard, meat-and-potatoes entree for himself.
Before the food arrived he went to the washroom, and she flagged me down, saying she was leaving and asked if she could pay her half. I told her no - he ordered everything, he could pay for it. She thanked me and bailed.
Took him probably 30 minutes to ask if she had left, and I explained that she had, and why.
And in the end, I got to eat the salad he ordered for her.
Hey_Colby, Pixabay/pexels
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171points

#5

40 Bartenders Reveal The Worst First Dates They’ve Seen That Range From Cringe To Heartbreaking
Some old guy was describing some "oddities" of his childhood and why his kids and grandkids weren't raised to believe in Santa Clause (because he wasn't either) and this old lady just would not drop the issue and when he gently requested that they change the subject, she started raising her voice calling him spineless, useless, a disappointment of a man, and by that point I'd had enough and just told her she needed to hit the road because she was being an a*****e and scaring off customers. Told the old guy his tab was on me and that I'd arrange for either a cab for him or for his "date". He didn't take me up on it, just left me a few $20 bills and they walked out together before he sheepishly thanked me.
Another sad one, a guy showed up to the bar when it was a touch slow, I got him his first beer and noted he was dressed pretty nicely. Being the chatty guy I am, I asked him if there was a special occasion or something. He said he was waiting for a girl to show up for their first date and was pretty excited. Guy hangs out a bit at the bar top for a bit before milling around, comes back and orders some onion rings and another beer. Things got a bit busier so I didn't keep close tabs on him, but then an hour or two went by and I noticed he was still there alone, and he looked a bit confused and saddened, so I asked him how he was doing, he said she hadn't shown up yet. Because I've been there, I got him a drink on the house and asked if he needed anything else. Hour later, the date finally shows up, completely plastered and they walk up together to sit down and she tries ordering some shots. I know most bartenders in most places won't really stop themselves from over-serving someone, but I told her "perhaps you should slow down a bit, here's a glass of water and a free soda". She knocked both over, demanded shots. Guy was clearly embarrassed. They put in a small food order and about 30 minutes later I saw him pouring her into a cab with a to-go container. He came back in and we just chit-chatted when we could for the rest of the night.
Dan, I really hope you found the right woman for ya.
HeroToTheSquatch
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169points

For many couples, a first date is enough to see if there’s potential for future interaction; especially when there’s probably not. “Typically it's because they got enough information to know the person isn't someone they can see having anything more with,” Lisa Concepcion suggested.

“I advise giving people three dates if you think you are attracted to them and like them after the first date,” she continued. “By the third date you can decide if they're a fit for you.”

#6

40 Bartenders Reveal The Worst First Dates They’ve Seen That Range From Cringe To Heartbreaking
Wasn’t the bartender, was the guy… started at a nice Italian place, and then we went for drinks and dessert at the latin bar across the street in Bay Ridge, Brooklyn. Group of mid late 30s-early 50s women next to us. An argument broke out at the table next to us, a lighter got thrown and exploded under our feet, their table flipped knocking all the dishes and glasses everywhere, shattered. One woman pulled out a box cutter and slashed the other across the forehead.
So. Much. Blood. Far too much to come back from.
We couldn’t leave till we paid our check so we just kinda sat there in shock for the next half hour. I ended up walking her home, kissed her goodnight and called it. Violent crime really does ruin the mood…
It ended up on Citizen app as “woman slashed” and we were in the videos background lol. Worst part was we worked together and didn’t want people to know we went on a date so we had to sit the whole day the next day and not say anything about it. The good news was that I took it as a sign from god to stop pretending I was straight and came out a few weeks later and I’m happy to report I haven’t had any violence or crime issues on any date since!
Tl;dr - Fight at table next to us led to a slashing, so much blood, now I’m gay.
AmphibiousMeatloaf, Rosemary Ketchum/pexels
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156points

#7

40 Bartenders Reveal The Worst First Dates They’ve Seen That Range From Cringe To Heartbreaking
Her husband walking in and taking her keys. Telling her not to come home. Then stopping right before he stormed out the door, turning abruptly and yelling “and f**k you mike, what the hell?!”.
armhat, RDNE Stock project/pexels
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148points

#8

I was a bartender at a restaurant, and this teenage kid shows up, 15 or 16 years old, all nicely dressed up, a rose in his hands. Says he reserved a table for two people but wanted to wait at the entrance for his date. He stood there and waited and waited, ordered a coke at some point, and waited a little longer. The longer he waited, the worse he looked. After 45 min it was clear that she was not showing up. He didn't have to pay for his coke. Poor kid.
butzbaam
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136points

According to the dating expert, people are often willing to see a person more if they are aligned on values and worldview, plus are attracted to one another. As for the reasons they might not be willing to, she suggested that there can be quite a few:

“They didn't share the same dreams, goals, ambitions. They drank excessively. They lacked manners. They seemed immature and non committal. They were hyper focused on sex, all conversations led back to sex. They weren't a person you could imagine bringing around your family. You regretted leaving your pet alone 30 minutes into the date. You didn't find them attractive.”

#9

40 Bartenders Reveal The Worst First Dates They’ve Seen That Range From Cringe To Heartbreaking
Was a bartender for over a decade, watched a guy leave the bar to use the bathroom, the girl he was with( first date) said to me,“ how many times do I have to bring a date here for you to finally hit on me?” I told her I was engaged and have zero interest , the guy was otw back from the bathroom and overheard her say that, proceeds to lose it on her in front of everyone, which is understandable, and they both scream at each other and leave the bar, that was their first date, and I have not seen anything worse since.
Lettheexpletivesfly, cottonbro studio/pexels
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135points

#10

So I’m scrolling looking to see if I recognize myself in a story.
I was in a bar with a former Marine on our 3-4 date. He’d taken me shooting earlier in the week. I don’t even know how the conversation started, but it ended with him screaming that I needed to learn to shoot left handed because if I was shot in the right arm, how else would I be able to defend “our family”?!
We barely knew each other and there was no family. It was so painfully awkward paying the bill. I had to ride home with him but never answered a call from him again.
Ok-Intention-4593
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126points

#11

40 Bartenders Reveal The Worst First Dates They’ve Seen That Range From Cringe To Heartbreaking
I was witnessing what seemed like a great first date. So well they started making out at the bar. He had long hair but a 5 head and bald spot. His hat came off in the heated moment and I saw the look on her face.
I saw her weeks later and she used the phrase "hat fished" and I'll never forget it. Still feel bad for the dude, he was super nice and paid for everything.
letsdotacos, Daria Obymaha/pexels
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124points

The expert emphasized that it’s important to think certain things through before going on a first date and to be honest both with yourself and the date.

“The key thing is to be very clear with yourself about your purpose for dating. Are you dating for fun and nothing serious? Or, are you dating to attract your spouse or serious long-term relationship? Once you know exactly what your intention is for dating, you gain confidence and can openly and honestly express what you're dating for.

“This is a very important thing to discuss on a first date and if possible even beforehand through an initial video call. Why waste time? If you are dating to attract your spouse you're not going to want to go on a date with someone who is recently divorced and not looking to get serious,” she pointed out.

#12

40 Bartenders Reveal The Worst First Dates They’ve Seen That Range From Cringe To Heartbreaking
I've been bartending for 20+ years and have seen A LOT of bad first dates but the one that will always stick out to me was the guy who had his mom vet his date for him. Like he was there at the other end of the bar but she had to sit and meet his mom first. They were the only 3 people in the bar at the time so it was suuuuuper awkward. I pretended to watch hockey but I was so intrigued I was eaves dropping the whole time. The poor girl seamed so lovely that she was too polite to just bail out of the situation so she actually did it! I immediately knew something was f***y when she walked in and got stopped by the mom on her approach to him. The guy seamed so comfortable that it clearly was not the first time it happened. So f*****g weird.
dunkan799, Karolina Grabowska/pexels
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117points

#13

40 Bartenders Reveal The Worst First Dates They’ve Seen That Range From Cringe To Heartbreaking
Working at a craft beer bar, this guy asked me out right in front of his absolutely STUNNING date and kept winking at me throughout the night. She left, he did not get my number.
Sea-Emer, cottonbro studio/pexels
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114points

#14

40 Bartenders Reveal The Worst First Dates They’ve Seen That Range From Cringe To Heartbreaking
Girl out with her friends ran into boyfriend who was supposed to be out with his friends...but was on a date. It turned into a whole thing in the parking lot.
Ok-University-9769, RDNE Stock project/pexels
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114points

“If you're both on the same page as far as what you want, then great topics are values-based topics,” Lisa Concepcion continued. “Asking open-ended questions such as ‘what was the last thing you splurged on for yourself,’ will give you a clear idea of how they are with money. Asking them how often they get to see their family will get you information on their family dynamic.

“It's very important to master communication and ask questions that encourage people to speak freely as you listen intently to gather data. Dating for data is all about engaging in meaningful conversation to learn more about the other person.

“It's also very important to have conversations about worldview, morals and values. You want to determine if you both are on the same page on important things that matter,” the expert emphasized.

#15

Was working a bar one weekday night. Woman comes in, orders a drink and sits at the bar. On the opposite end of the bar, a man comes in, orders a drink and takes a seat. An hour passes. They're sat in positions that block their view of the other. After an hour, I hear the man mutter, a f**k this, and put on his coat to leave. Heads for the exit near where the woman is sat. They spot each other, and realise what happened. Personally, if that happened to me I'd think it'd be very funny, but these two seemed annoyed with each other, didn't seem to talk a great deal and parted after about 45 minutes.
The biggest question of all really was, why didn't either text their whereabouts to the other hahahaha? Surely they had communicated beforehand.
crumumbooty
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108points

#16

Not bartender, but I was at a local red bird burger shop a week ago. Yum...
My wife and I are just chilling with a couple burgers and beer, watching a game. A couple comes in and sits next to us in a booth. Clearly a 1st date, both in late 30s early 40s.
Guy starts going on and on about himself and mid sentence, pushes his date out of the booth to stand, takes his hat off, and at full on attention, salutes the national anthem that just started at the game on the TV. He apologizes to everyone in the bar, (he is loud as s**t), and then tells his date that he's sorry, but as a former marine with buddies who died for the flag, he felt obligated to respect the anthem. Fair enough, I suppose.
The woman ordered a salad. He then critiques her choice, and then orders the exact same salad while letting everyone in the bar, again, know that he has all the allergies and if he eats, smells or even looks in the general direction of a tomato, he is bound for the afterlife.
He consumed his salad at Marine Corp bootcamp speed, and told everyone in the bar, again, that he eats fast because Marines.
He then continues to talk about himself the entire time, all the while the entire bar is now enjoying this s**t show. The woman never said a word other than ordering her food and asking for a box.
Turns out they rode together so the fun didn't stop after dinner. They rode off into the sunset in a mid 90s ram with no exhaust that would have garnered at least a participation ribbon at the County fair.
Chefman11
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106points

#17

40 Bartenders Reveal The Worst First Dates They’ve Seen That Range From Cringe To Heartbreaking
I was bouncing one night when there was a first date going on. (Was in earlier than my shift start time). His date went to the bathroom, he went up to the bar, pounded a few shots, then attempted to grope a woman sitting at the bar. His date walked out of the bathroom as I was hauling him out.
2_alarm_chili, cottonbro studio/pexels
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104points

While asking certain open-ended questions can help one get to know their date better, some topics are better left untouched on the first date. According to the certified love life strategist, they include complaints about work and your ex who is still driving you nuts, parents and friends.

“You don't want to treat a first date like a therapy session where you're complaining about what's wrong in your life. Avoid talking about how awful the dating scene is. Avoid talking about sex on the first date unless you are asserting a boundary. Sexual innuendo too soon gives off a predatory vibe. People want to feel safe.”

#18

There’s a bartender out there that probably tells people about the date I was on. Every day I suggested the guy had plans. We finally decide on a Sunday night, after I worked an 8 hour retail shift. I drove out of my way to meet him at the restaurant he chose. When I got there I texted to ask where he was and he said the bar. I had hoped for a table, but whatever. When I walked up he had 3 empty glasses in front of him. As soon as he started talking I could tell he was absolutely s**t faced. He admitted to drinking 2 bottles of wine before leaving his house. Needless to say, I was not impressed. When I asked if he drove, he said he took an Uber because I was going home with him and could drive. I hadn’t taken a break all day so I was starving and ordered an entree and a soda. He called me strange for not getting a drink. Then, when I wasn’t exactly thrilled to talk with a drunk, he kept saying “you’re so weird. Why are you so weird?” He kept trying to flirt with the bartender. She and I kept rolling our eyes. He finally got up to “take a p**s” and I asked for the check, paid, and left. He proceeded to blow up my phone calling me a n**ger lover and a wh*re. Super cool guy lol.
gonewildecat
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103points

#19

I was a bartender HOWEVER, this date happened to me and I'm just throwing it here because I can. I was on a first date and things were OK. A little awkward but nothing beyond first date stuff. 
The woman had ordered a drink but by no means was tossed . I made the horrible mistake of asking about her family and the first thing out of her mouth was "Well I'm pretty sure my dad was an uncaught serial killer."
She was the talker type and proceeded to tell me how he owned a cabin in the woods that was his man cave. Separate from the main house. Nobody was allowed there and nobody ever saw the inside. She said he brought her random jewelry after his trips to the cabin and she had to wear it nomatter if she liked it. 
I was horrified. I think she was just trying to be interesting but when she told it she was so nonchalant about it that it freaked me out. 
We never talked again after that date.
Remarkable-Let251
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101points

#20

Dude said that he’s an Alpha like 6x times.
cats_arecats
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101points

If you’re looking for more dating horror stories, we have quite a few in store for you; feel free to continue to this list of bad dates that ought to make you cringe or read about these dates that didn’t go well, or browse our romantic relationships category for more love-related tales.

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