Chicago Bartenders Share Their Worst Bar Stories

shots at the bar
Anthony Humphreys/Thrillist
Anthony Humphreys/Thrillist

Bartending can be a tough job. Sure, there are some perks, but dealing with people full of whiskey all day is about as enjoyable as trying to get to know your mom's on-again-off-again boyfriend. Fortunately, the job also tends to offer plenty of laughs, as evidenced by this collection of loopy stories that we culled from some of the city's most weathered drink slingers. Enjoy, and remember: Please drink (and live your life) responsibly.

Time to join

"I was working at a place in Lincoln Park, bartending. This guy came in for brunch and said he was meeting a Tinder date. I thought that was a bit bold for a first date, but hey, whatever. So, he started off by showing me a picture of his date, and he was so proud. Right away, I was thinking, 'This isn’t a real person.' It just looked like a model photo, perfectly backlit and everything. Something seemed off.

Of course, in walked a girl that looked nothing like the photo. She came in wearing this outfit -- let's just say that it was too small for her body. She sat down next to the guy, they started talking, and I could tell by the look on his face that he was bummed. They ordered bottomless mimosas. This was a mistake. At one point, he turned around to ask a waitress a question, but when his back was turned, his date immediately drank down her flute of mimosa, and then reached for the pitcher and proceeded to chug the whole thing down.

Initially, he was all surprised that the pitcher was gone, but he quickly realized what happened to it. So, I made them another one but put it by him so she couldn't just grab it right away. But she kept going for that pitcher, and within 20 minutes I had to serve her coffee. This girl was a wreck. She then started grabbing all on the guy. Eventually, when he went to the bathroom, she stole some drinks off a nearby table.

When the guy came back from the bathroom and noticed that his date had more drinks, he was like, "Can you help me?" At that point, she ran off to the bathroom. I think the guy was going to wait for her to come out and then split. But after a while, we figure out that she had passed out in the bathroom. We had to get a female worker to open the door, and she was found passed out on the toilet. This is still brunch time, by the way. So as this lady was getting physically taken out, she was grabbing drinks off of tables and out of people’s hands, which was a pretty bold move. Eventually, we got her outside and ordered an Uber.

A year later I was bartending at a completely different place. I heard this voice, but I couldn't quite place it. Then, out of the corner of my eye, I saw someone’s hand grab a tip off the bar. I turned around, and, lo and behold, there she was. She was on another date and I cut her off immediately. Before we threw her out, we checked her pockets and she just had wads of crumpled-up bills stuffed in there."
- John L., Lincoln Park

Next stop: Fear Factor

"One night, this gentleman was hanging at the bar. He was pretty tipsy and ordered a PBR as he was finishing his old one. A sober girl standing near him was staring at me, waiting for me to serve her. The guy drank the remainder of his PBR, but then threw up a little in the can. Obviously, pretty gross. Me and the girl saw everything, and then I grabbed a new PBR and told the guy that he was cut off. (All of this happened pretty quickly.)

Before I had a chance to grab the barf-filled PBR, a random lady had just taken a shot, grabbed said PBR, and took a big swig. Sober girl and I started yelling, "Noooooo!" but we weren't fast enough. Fortunately (or unfortunately, I guess), she just shook her head and danced back to the floor. She didn't even know. What a champ."
- Emily M., Logan Square

"I'm always stunned at the amount of people that try and have sex in a nasty bathroom."

I'll have what he's having

"One time at the bar, there was this sorta weird, twitchy guy who was sitting at the bar having a drink, minding his own business. He had a duffel bag with him, and he must've had it hanging from one of the hooks attached underneath the bar. People often stop by the bar before or after their flight at O'Hare, so it didn't look out of place or anything. Somehow he knocked the bag off and it hit the floor, spilling out its contents: five or six huge dildos and vibrators. I kid you not.

The woman next to him bent down to help him pick up his belongings, but when she realized what it all was, she started screaming. She just freaked out! He collected everything in a frenzy, went outside, and shuffled through the bag on the patio. But here's the weirdest part: Amazingly, he walked back into the bar while holding one of the dildos, looking around like a lunatic. One of the bartenders ran around the bar and walked him out. It was pretty bizarre."
- Greg M., Logan Square

Say hello to my little friend

"I used to work at a bar in Lakeview owned by this crazy Irishman. He was pretty old-school, and hated when people would do cocaine in the bathroom. So, he started spraying down surfaces in the bathroom with WD-40, which apparently ruins cocaine by making it congeal. It's a real thing, look it up. People would sometimes come out of the bathroom livid that all their expensive cocaine was destroyed, but what were they going to do? It's not like you can sue for that. And of course, the owner would laugh his butt off at them and then kick them out of the bar."
- Sean F., Lakeview

Don't tread on me

"For a while, my barback and I would work the bar on Tuesdays, and it wasn't always busy. So, we would get weird with it and unilaterally turn Tuesdays into Camo Tuesdays. We would only play Rambo movies on the TVs, dress in camo, and sell camo cans of Old Milwaukee on special for a buck each. We didn't ask the management about any of this. Our boss never came in on Tuesdays, but of course, he showed up one random day. He was like, 'What the hell is this?'

We just said that we thought 'this was a company thing,' which doesn't really make sense any way you slice it. He just left. Except, it turned out that the boss was a veteran, so on the following Camo Tuesday he showed up with some of his military friends. The bar wasn't too busy, so they spent the night yelling at us, calling us 'soldier,' ordering ridiculous drinks, telling us to 'drop and give me 20,' and generally making things difficult. It was pretty hilarious, but we didn't do Camo Tuesdays after that."
- Kelley S., Logan Square

"My favorite story is really weird. It involved a lady who broke into an area behind the bar, got naked, and eventually snuck into the owner's living area."

Caution: slippery when wet

"Most of the time, bartenders just witness people fighting, drinking too much, barfing, falling asleep, and then trying to convince you that they weren't asleep, or not knowing how to use toilets. However, I'm always stunned at the amount of people that try and have sex in a nasty bathroom. Like, there's a good chance moments ago someone was boning on the very toilet that you're using.

One time, I had this couple come and they were getting pretty loose. The woman was married, the guy was not. And he was trying so hard with her. He was feeding her booze all night, getting all close on her, lots of contact, real slimeball stuff. So eventually I realized that both of them were gone and it had been a little too long. Of course, I told the server to check in the bathroom and she came back saying that they were in there.

So I went into the ladies' room and they were in the handicap stall, going at it. Pretty much same ol' song and dance, except I saw that all their clothes were on the floor. As in, both these people were bare-ass naked in the toilet of this bar. I started yelling at them, 'You can't fuck in my bathroom! Get your clothes on and get the fuck out!' I went behind the bar, and when they came out of the bathroom, the woman looked mortified. But the guy, he didn't care, and they sat back down at their booth and tried to order another round.

I had to leave the bar again to inform this dude that they couldn't drink anymore and that they had to leave. The guy got defensive and asked why they had to leave. So, in a hushed voice, I asked him if he wanted the whole bar to know what was going on in the bathroom. At this point, the woman was pretty much about ready to tear his arm off. The guy gave me the death glare, but they paid and stumbled off into the night.

I saw them both about three weeks later. They were nice as pie. No funny business. So weird, but it's all the clothes on the bathroom floor that really gets me."
-Benny K., University Village

Is that cranberry juice?

"One time I was bartending and I witnessed a fight where two Tommy Bahama dudes were arguing at the bar. You know, the type with khaki shorts and loose Hawaiian-print shirts. Maybe they had a rough day at the golf course or something. Anyways, they were arguing and suddenly one guy grabbed a pretty expensive glass of wine and just smashed it into the other guy’s face. Just, blammo! It was like something out of The Departed.

Of course, glass went everywhere, but a piece broke off and got stuck in the guy's forehead above his eyebrow. Before I could tell him not to remove it, he pulled it out. Bad idea, since it basically was acting as a plug to stop the bleeding. Blood started going everywhere. At first, it actually squirted, and someone started screaming. I grabbed a bunch of napkins and pressed them hard on the cut while someone else called for an ambulance. He probably had to get a few stitches for that one. As for the other guy? He ran off in all the commotion. I quit a few weeks later."
- Graham D., Bucktown

No-pants party

"I've seen some crazy stuff working in bars: fights, domestic violence, nudity, drugs, unnecessary crying. I will say that fratty bros love to grab pool sticks and play air guitar with them, and they also love to compare bartenders to athletes. I once heard a fellow bartender get lambasted for looking like [former NBA player] Kevin McHale, and that was awesome. Another guy repeatedly said 'right on' for an hour. A woman once said she left a mess in the 'candy box,' which is code for the tampon disposal box, located in the women's restroom. One guy hit on women all night by saying his dad invented the concept of billboards. A few actually seemed receptive.

My favorite story is really weird. It involved a lady who broke into an area behind the bar, got naked, and eventually snuck into the owner's living area. She passed out in the hall, crawled into the bathroom, cops came, and she roared out of the bathroom (naked) like the ghost from The Ring coming out of a well. Then some dude, claiming to be her husband, came in and said he thought she might be there. The cops verified they're together, escorted them out, and they vanished into the night. She left wrapped in one of our towels."
- Frank B., South Loop

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One time at Rainbo Club, Raf Miastkowski told a joke to Saturday Night Live's Cecily Strong. She was not impressed. Send him better ones @RafFoSho.