Chicago bartenders tell us their craziest bar stories

From awkward first dates to things getting a bit too personal, Chicago bartenders reveal their best bar stories

Photograph: Clayton HauckBarrelhouse Flat

Everyone has a great bar story—whether it's witnessing an especially awkward first date or catching someone falling asleep at the bar. But they probably don't compare to the tales bartenders could tell. We asked Chicago bartenders—from cocktail bars4am bars and steakhouses—to tell us their very best stories. They delivered.

RECOMMENDED: Our guide to the best bars in Chicago

Stories have been edited for length and/or clarity.

Chicago's bartenders tell us their best bar stories

A quick dip in the waterfall

Sarah Crossley, general manager and bartender at The Owl

With a 4am license (5am on Saturday), Logan Square’s late-night hangout the Owl see its fair share of debauchery. The bar’s centerpiece, a woodland scene with a waterfall, is the focal point. I was tending bar one Friday night when we were super busy. Next thing I know, a guy climbs over the bar and tries to dunk his head in the waterfall. He then proceeds to sit down on the waterfall and put his head in his hands.

Logan Square

First date mix-up

Jimmy Hibbard, general manager at the Barrelhouse Flat

The Barrelhouse Flat has always been a hot spot for dates, most commonly first dates. The candlelight and ambiance can, however, have drawbacks. There was one night in particular when the usual push of first dates started to arrive. Among them were two men sitting at adjacent tables. They were followed by two women about 10 minutes later. The women approached the men, exchanged half-hearted "side hugs" and things seemed to proceed as normal. After about 15 minutes, something changed. There were nervous giggles and awkward room scans coming from both parties. The daters had matched up incorrectly, but it took them 15 minutes to realize it. What happened next only increased the tension. The women, seeing their "actual" dates, stood up, passed each other in a kind of duel-esque walk and joined the opposite men. Needless to say, the dates ended shortly thereafter.

Sheffield & DePaul

Get a room

Dylan Stewart, beverage director at The Ruin Daily

Before working at the Ruin Daily, I once had to stop a gentleman from performing cunnilingus on his partner/companion while seated at my bar. Does that qualify?

West Loop

Kids these days

Jess Lambert, head bartender at Vol. 39 and Boleo

I was in the middle of Friday night service at a tiny cafe in Phoenix, Arizona, when we heard a sudden loud sound of breaking glass. At first, I thought someone had dropped a bunch of plates, but then we heard loud bangs, which sounded like gunfire. Someone yelled, “Everyone get down!” I ducked behind the bar, and motioned for my four bar guests to crawl behind the bar with me. I seriously thought someone was shooting at everyone in the restaurant. What ended up happening was a bunch of kids threw a brick through the restaurant's front window. They then proceeded to throw firecrackers into the restaurant, which sounded like gunfire. I crawled out from behind the bar with my patrons, and immediately poured a round of tequila shots for us. 


An unexpected garnish

Danielle Lindow, assistant food and beverage manager at Hyatt Regency Chicago

I went out for drinks after work in Logan Square and decided to sit at the bar instead of waiting for a table. I ordered my drink and the bartender began to do some "flair." That part was normal—until he grabbed three ping pong balls and started juggling them with his mouth. When one of the balls fell into my drink, the bartender called it a "garnish." I called it waste spillage.


Now you see it, now you don't

Amy Witz, sommelier at Stetsons Modern Steak and Sushi

I was talking to a bartender in the Gold Coast who said she was recently her friend’s assistant in a magic show. She asked if I wanted to see a trick, and she blew up a three-foot-long balloon and then swallowed it.


Puddle jumper

Zach Rivera, beverage manager at Headquarters Beercade River North

There was a very large crowd of people standing outside the bar after we closed, and I was trying to get them to move along. I approached a barefoot girl in a nice dress. She was intoxicated to say the least. I politely asked her to go with her friends down the block and she quickly became angry. She accused me of hitting on her, told me I was gross and asked me to leave her alone. What she didn't realize was that she was standing barefoot in a puddle of her own urine.

River North

Where to find the best cocktails in Chicago

Cocktails in Chicago

Whether you're looking for your next stop for a drink or want to try to make one yourself, we've got you covered with our guide to cocktails in Chicago.

By: Elizabeth Atkinson