The Worst Date Stories From Austin Bartenders

attractive people standing at a bar
Comaniciu Dan/Shutterstock

Bad dates are a fact of life and, barring an intriguing Catfish-style twist resulting in some MTV facetime, the only options for disastrous daters are to either stay and double down on drinks or completely ghost out. What bad dates have in common, though, is that they often start and end in a bar and lucky/unlucky bartenders get to see these train wrecks develop live and in person. So, next time you’re at a bar sucking face with a Tinder rando or having a rendezvous with a lady of the night, remember... know that they’re watching (tip them accordingly).

“During SXSW a celebrity couple (that we cannot name) had an elaborate date...

... at Swift's Attic. Hours go by, and they totally trash the bar area. We had a buyout that night, so we get them out and quickly get everything cleaned up. The evening event gets going, everything is going smoothly... and then here comes the celeb couple, and they’re three sheets to the wind. They aggressively push their way into the party and demand free drinks despite it being a private party that they weren't invited to. Then they went into the classic 'I'm a celebrity, give me free drinks' mode. And, I did what any bar manager would do in this situation... escorted them right out the door.” --Curtis Hansford, bar manager at Swift's Attic

man and woman prostitute flirt in the street against a car

“So while bartending one night at The Highball’s old location...

... this couple sits at the bar. The are obviously on a date and the woman is dressed to the nines -- straight lookin' like she is ready for prom with an up-do, and tons of makeup. The guy pretty douchey; he’s in pleated slacks, a Hawaiian shirt, and a fedora. Those of us behind the bar couldn’t figure out why was she out with this guy. They order drinks, he’s bragging about himself; this goes on for a while. Two female coworkers get off work, sit at the bar next to them and get to chatting with the woman, and when my shift is over all of us decide to move the party to a karaoke room.

So now my two female coworkers, the douchey guy, the lady dressed for prom, and myself are all partying and drinking together, in the Jem and the Holograms-themed room. While the dude goes to the bathroom, the woman divulges to us that she’s a prostitute and can’t stand the guy aside from the fact that he pays well. The guy comes back in the room and immediately starts pulling wads of money out of his pockets and suggests that all three girls go back with him to his car to 'get it on.' Me and my two coworkers laugh it off and leave. When we go outside to smoke, we see the couple getting into his love-machine -- in this case a rusted early-90’s Astro van with dents and the bumper being held on with bungee cords and duct tape. Some player! We died laughing.” --John Bowley, bartender at The Highball

man and two woman at a bar/lounge having drinks

“At one time, I worked at both a swanky lounge...

... that serviced those who wanted to keep a low profile and also a well-known restaurant/bar, the kind of place you take a date on a Friday night. One regular at the swanky lounge wa this guy named Rick who always visited with his man-friend. They were very affectionate and we just assumed they were a couple. Well, one night while I working at the other place, the restaurant/bar, Rick walks in with two ladies. He sees me, gives me a deer-in-headlights look and immediately introduces his wife and her friend in an uncharacteristically deep, manly voice. While they sat at the bar, he was obviously nervous, so I poured him a few stiff drinks. He relaxed when he realized I wasn’t going to 'out' him. As the night went on, he continued to tip me very excessively. And the even better part? I got to hook up with his wife’s friend. It always pays to be a bartender who can keep a secret.” --Javier Flores, bartender at Midnight Cowboy

woman waiting at bar with a drink, on her phone

“Recently, a pleasant-enough young woman sat down...

... in front of my well and had a cocktail while waiting for her date. I couldn't suss out if it was a traditional blind date or a or Tinder or whatever but they clearly didn't know each other. Her date was a man of some quasi-prominence, being the proprietor of a nearby fast-casual food-truck-turned-brick-and-mortar. Several gin and tonics later, we realize he is either not much of a drinker or just very bad at it; this guy actually got lost trying to return to his seat from the bathroom and ended up wandering down the street. As if that wasn’t bad enough, then I had to ask his (still very sober) blind date to fetch him so he could pay the check.” --Justin Elliott, Partner at The Townsend

couple having drinks at a bar

“I was working at a place in SoHo that regularly saw NYC fashion industry types...

... and massive numbers of Japanese tourists (this is years ago, and happened before I moved to Austin). This couple comes in, they're Japanese, but he's also clearly in fashion, rocking a full length, blinding white fur coat. It seemed to be going fairly well; their conversation was at least animated, but it was happening in Japanese, so I couldn't tell you what was actually being said. Suddenly, the woman stood up, dumped a full glass of red wine over the top of the guy's head and stormed out. As the wine seeped into his fluffy white fur coat, couldn’t help but think that he looked like a clubbed baby harp seal.”--Bill Norris, Beverage Director at Alamo Drafthouse

lonely woman at a bar looking sad
Diego Cervo/Shutterstock

“Years ago, I was bartending and noticed a guy come in alone.

The reason I noticed him, is he was dressed like he was straight out of a bad 80's movie -- neon jacket with shoulder pads, acid washed jeans feathered hair, white sneakers... the works. He stood out like a sore thumb. It was as if he hadn't left the house in 20 years. He sat alone for a long time, only ordering water and we all watched with great confusion and curiosity as he repeated several times that he was waiting for someone. When the someone (a woman) arrived, she was tall, gorgeous, and obviously on a first, perhaps blind, date with this gentleman. Plenty of servers circled the table to eavesdrop to try to figure out the situation. She ordered a glass of wine, he ordered a beer. It was obvious right away that he wasn't what she expected and based on the look of them, they were not a good fit. About 15 minutes in to the 'date,' she excused herself to the restroom. Minutes later, we saw her jumping into a cab. She totally ditched him! It was funny but then we just felt sorry for him and comped the drinks and the food that hadn’t even come out yet. Poor guy, I guess she wasn’t into the Miami Vice type.” --Jen Keyser, Chief of Bar Operations at Hotel Van Zandt

Man passed out at a bar surrounded by drinks

“On a slow-ish Sunday night a guy walks in and orders a shot...

... and he proceeded to inform all he was meeting a lady on a blind date and that he hoped she wasn’t 'busted.' Then his date walks in. After an awkward 'hello' and half hug, she tells him that he stinks of booze. Thrown off by the remark, he gave her a snarky, 'Well you're cute.' The conversation downhill from there; he complained that he couldn’t find a job, then he berated her for wearing too much makeup, THEN he asked her if she could give him a ride to a friends house after the date. This goes on for a few more minutes and they go outside to smoke. The girl comes back in, obviously disturbed by her date, and tells us she wants to bail but doesn’t know how to go about it. As she’s speaking we look behind her to see him passed out at a table; and... the date ends with me kicking the guy out of the bar and watching him stumble across the street to the corner store. The girl was super cool and hung out until the end of the shift. Sadly, I’ve seen her twice since then... on equally horrible dates.” --Fidel Campbell, Bar Manager and Bartender at Weather Up

two men and a woman enjoy whiskey and cocktails at a bar

“A man sits at the bar and overhears that the most expensive pour we have...

... is $95, promptly orders a double rocks. I let him know that I’ll need a card and he plops down an Amex black card as I pour the drink. Shortly thereafter his wife and another couple arrive. During this double date he tells multiple stories about his escapades in Dubai. They all seem to involve prostitutes and extreme spending. During this time, he knocks back what amounts to be about $800 worth of whiskey. The hilarious part of this exchange were the faces of the conservative couple sitting across from him and his wife -- who was obviously desensitized to his antics. Their faces revealed reactions of complete shock and confusion. They stayed about two hours and drank very little. It was like watching Ned and Maude Flanders dine with the devil, kinda cool.” --Bob King, Bar Manager at The Townsend

intimate couple making out at a night club
Monkey Business Images/Shutterstock

“A couple walked in who were clearly on some sort of Tinder or OKCupid date...

... we know this based on their conversation. They move to a table, not even twenty minutes go by and we notice something seems odd. The guy under the table going down on his lady-friend right there in a room with over two hundred people! We politely approach the table, explain that their behavior isn’t allowed and cut them off from drinks. Less than 10 minutes later we look over... and now he's got his hand up her dress. This time we ask them to stop and to leave and they do. Fast forward twenty minutes... a server comes over to tell us he found them having sex in one of the empty karaoke rooms upstairs! So, technically this was a great date for them... not so great for us.” --Jed Anderson, Bartender at The Highball

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Anastacia Uriegas is an Austin-based writer whose worst date ever was with a unicycle-riding amnesiac. Follow her other misadventures at @anaurie.