30 Of The Worst First Dates Bartenders Have Witnessed

A first-date meeting is usually reserved at a neutral location. This can mean a restaurant, a bar or even a coffee shop. But what it also means is inadvertent witnesses to the whole affair such as other patrons, waitstaff and bartenders. 

#1 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 it’s not a five star restaurant but a decent beach bar. She seems a bit put out but the date stumbles along.

Image source: Great_Kitchen_371, Andrea Piacquadio/pexels

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-.

#2 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.

Image source: HeroToTheSquatch

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.

#3 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.

Image source: Ok-Intention-4593

#4 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.

Image source: crumumbooty

#5 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.

Image source: Remarkable-Let251

#6 It was a few years ago. They were hanging out at the bar, she was excited and they were chatting happily. They were classmates who hadn’t seen each other while Covid lockdown was happening and clearly over the isolation. She went to the bathroom and he looks at me, sighs and says, “it’s rough out there” He was faking all the interest in their whole conversation and left with her to get laid. Ugh. Gave me such ‘ick’ that he was so good at humoring her despite his entire lack of interest.

Image source: InimitableMe

#7 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.

Image source: IceFireHawk, Hatice Bara/pexels

#8 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.

Image source: AmphibiousMeatloaf, Rosemary Ketchum/pexels

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.

#9 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.

Image source: Sea-Emer, cottonbro studio/pexels

#10 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.

Image source: Chefman11

#11 Dude said that he’s an Alpha like 6x times.

Image source: cats_arecats

#12 Her husband showed up and he was PISSED.

Image source: dirtylaundryrecords, Crypto Crow/pexels

#13 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.

Image source: Wesmom2021, cottonbro studio/pexels

#14 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.

Image source: Lettheexpletivesfly, cottonbro studio/pexels

#15 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.

Image source: dunkan799, Karolina Grabowska/pexels

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 seemed 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 seemed so comfortable that it clearly was not the first time it happened. So f*****g weird.

#16 A guy pulled out a tech deck ( finger skateboards ) and was bragging that he was pro, showing tricks on the table. I felt so bad for the girl.

Image source: BoatsAndHoesQC, David Merzan/flickr

#17 Dude showed up an hour before his date and got hammered. Fell off his bar stool during the date at one point. She left with friends. Hard to watch. He seemed genuinely excited about the date when he got there.

Image source: Something_Etc, cottonbro studio/pexels

#18 Some douchy guy came in and proceeded to hit on me and was super cocky in how he was amping himself up. Said he was waiting for his date to show up. She was a pretty but shy girl and it looked like the first time they were meeting. He proceeded to act like he was such a hot commodity and she was lucky to be on a date with him. Talked about how rich he was, how hot his exs were and what a good lover in bed he was. Made comments about how i was pretty right in front of her etc. made both of us extremely uncomfortable we both didnt bother to laugh or entertain. Sadly she seemed upset because he was critisizing everything about her. I shot him dirty looks all night and he tipped less than 10%.

funny enough he came back a week later with a conventionally pretty girl and all of a sudden acted like he was sophisticated and classy. Acted very mature and she looked like she didnt even want to be there. I noticed him catering to her every need like offering to buy her anything she wanted and buying an expensive bottle of wine. Absolute garbage of a man.

Image source: Dokays

#19 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.

Image source: Hey_Colby, Pixabay/pexels

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.

#20 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.

Image source: butzbaam

#21 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.

Image source: Ok-University-9769, RDNE Stock project/pexels

#22 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.

Image source: gonewildecat

#23 A younge man and woman walked in clearly on a first date. The woman proceeded to sit down on one side of the booth they were sat at. The man proceeded to attempt to sit down next to her, to which she got up and moved to the other side of the table. The man followed her again so he could sit next to her rather than across from her.
When their menus were brought over (the food was predominantly Indian food) , the man proceeded to loudly proclaim that he ate indian food all the time and that he could never find a place that served it spicy enough. When the server returned, he proceeded to order for both of them (terribly mispronouncing both dishes I might add). When asked if they wanted Naan, he asked what it was before saying no. While waiting for their food, he continued to brag about eating all different kinds of spicy food and barely let her talk. When their food arrived, he was struggling to eat the food and was visibly sweating. Afterwards, they quickly paid the checks and left. I do not think there was a second date.

Image source: joadgr

#24 I assume he was a finance bro. He did a line before she came, only noticed because he was rubbing his nose immediately when he came back. Told the girl that he’s on a biz tear and that if she plays her cards right she’ll get a YSL BAG. then proceeded to tell her that he wants to do c*ke of her t*ts. Needless to say she left and I laughed.

Image source: Mighty_Malaka

#25 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?!”.

Image source: armhat, RDNE Stock project/pexels

#26 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.

Image source: letsdotacos, Daria Obymaha/pexels

#27 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.

Image source: 2_alarm_chili, cottonbro studio/pexels

#28 I was a bartender at a restaurant. A 13 year old boy came in for his first date with a 13 year old girl. His mom brought them. She planned on getting them seated at the table and then leaving them alone to come eat at the bar herself.

Image source: esoteric_enigma, Kindel Media /pexels

The boy would not let her leave. The girl hinted multiple times about the mom leaving. The mom hinted about leaving too. He just ignored them. Finally, the mom says she’s leaving to give them some privacy. When she tries to get up, the boy reaches out and grasps her arm and tells her not to leave.

They all sat there awkwardly at the table. One of the servers heard the girl in the bathroom on the phone making fun of how weird he was being about not letting his mom leave then.

#29 I was bartending at a causal fine dining seafood restaurant on a Monday night. An older man probably in his mid 60s comes to the corner of the bar and asks me for a glass of our “best red.”

Image source: MotleyCute, cottonbro studio/pexels

I give him the wine list and he selects the most expensive glass which he cannot pronounce. He tells me he’s waiting on someone as he sucks down the glass. He pays for it, and continues to wait. About 20 minutes later he orders another glass, and tabs out again. Roughly an hour after he got to the bar, a woman probably 10 years younger than him shows up. The man turns around and loudly says in a disappointed tone “wow, you don’t look anything like your picture!” She sits down despite his comment and orders a glass of house Chardonnay. I checked on them occasionally but neither of them wanted to order food. Every time I tuned into what they were saying I noticed that only he was talking and it was mainly about all his surgeries.

When a bar table freed up behind them, the man looked at me and said “we are sitting here and I am having dinner.” He stood up and sat down before she could even answer. When I brought menus over to them he pointed at something random, and she ordered a small pasta dish. He continued to only talk about himself, and showed her pictures of his ex wife throughout the meal. She barely spoke. Towards the end of the meal he looked at her and said “have another glass of wine.” She declined. He replied with “what do you think I’m going to do?! Take advantage of you?” And turned to wink at me. She pushed her plate away, and asked me for the check. Once the man said he was going to pay, she grabbed her purse and left.

#30 Not a bartender, but I went to a pub with my then girlfriend around six or seven years ago. Guy comes in and sits down at a small table for two. Waiter brings two menus and a pitcher of beer with two glasses, even though he’s by himself. It’s obvious he’s waiting for a date. Over the next 60-70 minutes, he kept checking his phone more and more. He ordered his food, he ate probably half of it. Around 90 minutes after arriving, he realized he’d been stood up and just started ordering what looked like jack and cokes. Powered through about seven or eight of them, while just staring blankly at the wall. He paid his tab, got up and stumbled out and walked down the street. Felt really bad for that dude.

Image source: TheBoomExpress