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

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.

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.

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.

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.” 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.

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.

Her husband showed up and he was PISSED.

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.

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.

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.

Not a bartender but I remember I was eating at the bartop and there was a date going on beside me. I eat alone a lot and work long hours so I was watching TV. This dude interrupts my me time to ask me what he thought he did for a living pointing out how clean his hands were. "Oh IDK an accountant" there's infinite jobs you can do with spotless hands. Then he went on like a 15 min rant about how he has the best job in the world as a scrub nurse and how every day he gets to see naked women which is extremely creepy knowing he's talking about unconscious women about to be cut open... She noped out of there shortly after and I told him he's delusional thinking that he has the best job.

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.

I was working at a bar in my town when i was 22, some dude and this hot chick come in and ordered a few drinks, basic stuff but then after a while he got real drunk and intoxicated and starting throwing a hissy fit, The owner which we'll call Tammy had to come out and kick the guy out.

Few days later he came back apoligized and found out the lady he was going to date was a local gold digger, as he was complaining about it to his friend that lived next door he told Tammy "Thanks for kicking me out, might have not found out she was a gold digger if i hadn't have been kicked out" Then the man paid for the slight damages he caused to the bar seats and some dishes.

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.

I actually knew the girl from several years back, only realised after the fact after she'd left.

Her and her date seemed to get along ok at the start, but after about half an hour neither of them seemed to be talking. For another half hour they kinda didn't say much, looking at their phones a lot until the guy literally just got up and left. She decided to just take out her laptop and work on some Photoshop project for a while before heading off.

They were talking about the angel shot/cocktail and it's implecations. Both knew what it was. She ordered it in front of him. He just got up and left. She ordered a pound of wings and cried while eating them.

Not a bartender, but I order some hot wings with ghost pepper sauce from one.

As he watched me eat the first wing, he told me about the last guy who had ordered them. It was a young guy in a suit who was clearly on a first date with the girl he brought along. The guy boldly ordered the ghost pepper wings trying to impress her, took a couple of bites, got up without saying a word, and walked off. After 30min or so, the girl realized he wasn’t coming back and angrily got up to leave… but the bartender had to stop her and reminder her that she still had to pay for the wings.

I saw an uptight dude with what amounted to almost a hippy chick. Our place had a thing where we would cut off your tie if you wore one in the establishment (we'd give you a free drink). It was just something neat to do to say work time is over. Well, this dude was in a suit and tie, when I came over with the giant scissors, he freaked out. He thought I was joking, and she was laughing her a*s off. He decided to take off his "$150 silk tie, a*****e" instead of getting it cut off. She thought this whole charade was the greatest thing ever.

I did my usual spiel offering food and specials, and he was rather indignant, all but mansplaining to me how he's here with a purpose, which just made her burst out laughing again. They ended up getting dinner, and more drinks, she was really into him for a while, or at least looked that way, but as the night went on, her body language definitely changed. I'd bust in with new drinks or whatever when they looked like they needed something. I'd make her giggle, and he had no sense of humor, it was such an odd pairing. Throughout the night, I did see him smile, and he was a handsome dude, but he was tight as a frog's a*s.

After about 90 minutes to 2 hours they had worked up a $140 tab. He decided to close out, I give him the tab, he frowns, I already know I'm not getting a tip. He ends up tipping like $20, so about 15%, so not bad, really. At least he didn't pull out a calculator to figure out the tip (this was long before cell phones, much less smart phones), he seemed like that type of dude., So I did get a tip, albeit a small one.

At least from him, his date left me a $50 bill and her phone number.

Man, do I miss being young and skinny.

Not a bartender but right there. I was at a mom and pop shop. It had a stone fire pizza oven and the pizza station was right behind the racks for the alcohol. Some dude game in with an Italia shirt on and made sure to sit at the two seats that are three feet from the pizza guy (me). This guy was super Italian American and it was clear that was his whole personality, he looked and talked like a side character in the soprano's. They both ordered pizzas and he just sat there and talked about how traditional this pizza was and the art behind it (I had been working there for 2 weeks and had never worked a stone oven before that, also this is a small shop in the middle of Boston, and Cape cod, so not traditional at all, the owner and chef weren't Italian at all). The girl was clearly pretty shy and reserved and didn't say much. I was uncomfortable and I wasn't on the date. Eventually they ate and the guy asked if they should go back to his place. She just very shyly said that she would wait for a ride from her friend. He had already paid he got a bit upset by this but tired to play it off as her wanting to take it slow. As she waited alone I slid her a free garlic bread (I felt bad and I couldn't do much but it was something).

The one I can distinctly remember involved her using the phrase "my ex" three times in the first five minutes.

Ex showed up to the guys date, sat down while they were eating and introduced herself and started flirting with him in front of her.

The guy had friends there and they all could not believe it you could hear a mutual wtf being said when she walked to their table

The ex was pretty hot and was a Miss World Runner up.

He left with the ex lol.

Best worst was the one where she went home with me instead.