My Bartender Broke Up With Me

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Throughout the work week, my life revolves around consistency. I get my morning coffee from the same Dunkin, take my morning dump at the same time (10:15), and I go to happy hour at the same bar Tuesday-Friday. I can already smell the judgement and I love it.

There are few things better than being a regular at any establishment. Whether that place be a coffee shop, a diner, or a strip club; it’s nice to have that feeling of home every time you walk through those doors. And in my case, that home away from home was the dive bar next to my first job. For my friends and I, it was our “Cheers” in a big city with millions of people. And as of last Friday it all came to an end.

To really understand me, we have to go back 3 years to when I first entered the corporate world. I was 22 and greener than a leprechaun’s taint. I had much less salt in my salt and pepper and was still rocking a 32 inch waistline. It was a much simpler time. Though I had spent my undergrad years a stones throw away from the city, I still had yet to learn the ins and outs and hadn’t yet established a postgrad crew. Thankfully I’m a loud mouth with a penchant for chain-smoking outside of my place of business, which is how I met 90% of my current friends who are all likeminded degenerates from my old company.

They all happened to be a few years older than me and were more than happy to show a young buck the ropes. And those ropes took us to the two story Irish bar across the street- it was the beginning of my postgrad existence. Within the confines of those beer soaked walls I would go on to make many friends, take many shots, and smoke many cigarettes while heckling pedestrians from the upstairs balcony.

I celebrated my 23rd birthday, was given the offer for my current job, and had my first ever corporate going away party at that bar. And through all of my experiences in that bar, there was one person who spent every damn one of them with me, and it was the bartender on the second floor named Jen.

Jen had been the bartender at this fine drinking establishment since it’s doors opened in the early 2000s. She was everything you could ask for in a bartender. She knew my name after meeting me one time. She always gave us at least a 20% discount on our bar tabs, which is impossible to come by in this city.

She’d see me come up the stairs and would have my order ready for me by the time I reached the bar (Budweiser and a shot of Jameson, respectively).

When we would have sponsored industry parties, she would always let us know when the open bar was running out and would make us priority over the rest of the leeches who only showed up once a month for corporate happy hours.

When I was a broke entry-level squid, she would knock a few beers off my tab even though she knew I couldn’t afford to give her a proper thank-you tip. She actually became a part of our friend group as well and would go out with us when her shift was over. Needless to say, we had a very unconventional server-customer relationship.

Then two weeks ago we got the shock of a lifetime. Jen gave us the unfortunate news that she was moving to another city and therefore leaving her esteemed position as our personal beer-keep. Needless to say, my friends and I were beside ourselves. Could we still come to the bar? Would we get the same deals? Is she just fucking with us? Granted we all knew this day would come and that we’d all have to move on, but we all thought it would be at least a few years before this became a reality.

We are all very happy for Jen wanting to move on from serving a bunch of idiots who are frustrated from work on a nightly basis, but it’s weird to know that she won’t be there the next time I walk in.

Do I sound like an overdramatic drunk? Probably. But to me, and most certainly to my older friends it’s more than just losing a bartender. Jen was a staple of our after work life and she knew all of us inside and out.

She’s seen all of us go a little too far and get absolutely homeless drunk on a Wednesday night and never passed judgement. She’s a savvy business woman and walked away from those nights with some very healthy tips. She witnessed the first time I drunkenly attempted to spit really bad game at my current girlfriend. Shit, she even met my mother. She was a constant in an ever changing environment- she was stability for us. As a common man in a big bougie city where life is a never ending pissing contest, it was nice to have the familiar feeling of home somewhere.

Since I’ve been sick for the last few days, alcohol hasn’t even been a thought in my wettest of dreams so I haven’t been back to the bar since Jen left. I plan to make a comeback in the next few days. I know it won’t be same for any of us at our once favorite watering hole. Only time will tell if Jen’s replacement has the chops to even clean her shot glasses..

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Kevin Caulfield

Chicago based stand up comedian. Writer. Idiot

• @TheKevinC__
• @TheKevinC__