The Hazards of Dating Hipsters

by: Melinda McIntire

Note: This piece was also performed at Solo in the Second City, a monthly Live Lit show in Chicago that the author co-hosts. Coincidentally, the next one is this evening, Tuesday June 19 at 8:00, and Nico will be reading at it. You should come out. You can find the event on Facebook here.

Ah yes, hipsters. There is nothing that will make me take off my clothes faster than a dude who wears plaid, calls himself an artist, collects vinyl and has a beard. You want to know how to get in my pants? Wear pants that are tighter than mine. There is just something about dudes wearing nerdy black rimmed glasses and ironic t-shirts two sizes too small that just makes me hot.

A year ago, I moved to Ukrainian Village after 4 years of living in Lakeview. While I have loved the hipsters for quite some time, in Lakeview, they are an anomaly due to the influx of the Chads that graze on the Northside. After moving over here to the outskirts of Wicker Park, I was overwhelmed with all the options. Fish in a barrel my friends, fish in a barrel. The hipsters, of course, run rampant in these parts and soon I was having my choice of flavors.

Flavors including the Logan Square hipster, otherwise known as the LumberJack hipster. This one who reads Chaucer all day at Mustache Cafe and brings his books to Bonnys and takes notes in the margins while drinking his PBR and wearing his newsboy hat…but when asked, “What do you do for a living?” has no answer, but will debate with you to show you how smart he is. For example, I actually was quizzed by one of these Logan Square hipsters at a Milwaukee avenue establishment concerning the facts of the Reformation and Martin Luther’s 95 theses. Oh, you’re just so smart dude, I’m so impressed.

Or the Wicker Park hipster, otherwise known as the Urban Outfitters hipster. The vanilla of hipster. The hipsters who can afford to live in Wicker Park in a huge multilevel loft and who spend hundreds of dollars to look poor.

Or the musician/rapper/DJ hipster. You can find them all over the northwest side. They go by aliases and don’t actually know each other’s real names, though they’re upwards of 30 years old. This is my favorite flavor as of late. The peppermint custard of flavors.

And with this love of hipsters, has come quite a few hazards that are unavoidable:

The first is sex with skinny jeans. Taking off skinny jeans is the most unsexy process. Nothing will kill my mood faster than dude having to take his time to pull off his tight ass jeans. Guys are supposed to be able to just drop their pants at any moment, Marky Mark-Calvin-Klein-ad style. Having to hop around on one foot while peeling off your second skin pants, just no.

And the best part is in the morning when he mistakenly puts on YOUR H&M skinnies. Hot.

Hazard number 2: They all know each other.

They all went to art school together to earn a degree in art direction, film, or photography. I used to be employed by one of these art schools, which contributes to knowing all these hipsters.

They all run in the same circle. I can’t throw a rock into the crowd here at Cobra without hitting someone who knows 3 of my ex boyfriends. It doesn’t matter where I meet them– online, through work, at a bar, there is absolutely no doubt that they are roommates with some dude who I was banging a year ago.

Hazard number 3: You have to go to their gallery openings/underground rap shows/ DJ nights/ film premieres.

Since of course they all went to art school together, supporting their artistic endeavours is key. I still get text messages from my indie filmmaker ex asking me to come to his random film premieres. Yeah, ‘cause that’s what I want to do– get in a room with 22 other girls who you have banged and the current one you’re banging now.

I am continually the groupie behind the DJ booth at the watering hole where they charge $9.00 for a vodka tonic in the middle of Wicker Park. “Excuse me, $9.00? Don’t you know I’m fucking the DJ?” Isn’t that worth something anymore? At least a drink discount!

And who doesn’t want to spend their Monday nights at his rap show in Pilsen with a bunch of 22 year old hipster kids doing lines in the bathroom when you have to go to your 9 to 5 job the next morning?

Which brings me to my next point.

Hazard #4: Hipsters’ sleeping patterns and the hours they keep

I actually hold and maintain a job. One where I regularly have to appear at work on time. And yes, it is every day, Monday through Friday from 9-5. Like forever. Because no doubt, though they always ask if you have to work the next morning.

Yes dude, I ALWAYS have to work. I always have to be there at 9. I always get off at 5 pm. I promise it’ll be the same way next week when you ask.

I understand the hours at Forever 21 change each week, but my job is ALWAYS CONSISTENT. And yes, this does mean I need to get a decent amount of sleep tonight, and yes, this will be a challenge with your 6 roommates, who consist of a rickshaw driver, trust fund baby, drug dealer, and whatever else means they can stay up til 5 a.m. on a Tuesday night and party with zero consequences.

Hazard #5: Their dwellings

Ah yes, not only do they have those 6 loud roommates, they come with 3 cats, smoke cigarettes inside, and sleep on futons with broken slats. There is really nothing like waking up, smelling like cigarettes and cat pee, on a broken ass futon. How about you just come to my place? Which has a bed, and even a toilet that was cleaned at some point in the last 14 months. And things like bowls and silverware. Fancy I know.

Oh yeah, or they live at home.

Hazard #6: Bringing them home to mom

And of course he’s gotta be the one for me if he has more piercings on his face than I do in my entire body. Which fall out in your sheets at night only for you to step on and end up in excruciating pain because their face jewelry got lost in the carpet two weeks ago.

And the tats. Fucking emo hipsters and their tattoos. Seriously, my last so called boyfriend had a tattoo on his forearm of a Alice in Wonderland slitting her wrist. Now that’s a guy that just is perfect to bring on home to mom and dad.

Hazard #7: They are always broke, though have plenty of money for cigarettes/booze/drugs and whatever that new hipster trend item of clothing that he must have.

I mean paying for dinner? No. And not because they’re saving up for law school or because they’re making a living saving children in orphanages, no. I mean, remember, they live at home or with their 7 roommates, so it’s not that they have bills like paying for heat or groceries, no. It’s because they’ve spent their money on drugs and cigarettes and those damned expensive skinny jeans and whatever other hipster piece of clothing is popular that week. But buying you dinner, oh dear god no.

Yet even with all these hazards I list for you tonight, I can’t get enough of their artsy emo selves with their high tops and custom flat brim hats. But hey, I figure it’s gotta be better than the Lincoln Parks Chads I was dating prior to them, right?

Oh wait, at least the Chads work in banking and can pay for a drink or two.

Melinda McIntire is a local Chicago writer and socialite. You can find her at, writing about the single life in Chicago at and living out her last few days as a twenty-something. She is scared of birds, can’t snap her fingers, and is searching for the man and/or manhattan of her dreams.

One response to “The Hazards of Dating Hipsters

  1. The sad, frustrating story of my entire life.
    There is so much truth here, it’s like flashing a giant, critical mirror on Toronto. It’s always good to be reminded I’m not alone!

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