Can I Masturbate in OUR Shower? My Three Months in Chicago

“Nobody cares about your hangover. Ever.”   -Harriet Tubman

I live by that quote.

But I assure you, this wasn’t a hangover. It was a crucifixion, a deadly assault on my body.  Catatonic in my bed I began asking myself questions like:

  • Why do I need two water bottles of vodka to enjoy a concert with my best friends/favorite bands?
  • Did my nine hour blackout screw it up with that girl? Am I glad? Is it easier to miss someone than be with them?
  • Am I knowingly inducing hangovers because it’s easier to self-loathe than improve

I’m not exaggerating in saying it was easier to move across the country than to answer these questions. I know because in the middle of the night I found a sublet on Craigslist, booked a flight, and one week later I was in Chicago.

No job? And why Chicago?

Chicago because it’s cheap and I knew people there from college. $650 for rent including utilities is affordable on food stamps and I had something just slightly better: Three part-time jobs online, meaning they can be done anywhere with an internet connection.

And because I DEFINITELY wasn’t moving just to recreate college, and because things never go as planned, I figured my time in Chicago would be exactly like college. Exactly.


Well, was it? WAS IT?

NO! lololol much more despair, but before I get into that let me tell you a bit about Chicago, The Second City.

In the early 1800’s a group of Manhattan hipsters decided to move to the west coast to get away from their asshole parents and airborne scurvy.

Unfortunately there was passive-aggressive bickering over what music to play in the covered wagons, so the hipsters stopped by what’s now called Lake Michigan to settle the playlist once and for all.

But it was a pleasant Fall and all the leaves were neat colors so they said fuck it and decided to stay because this was probably the Pacific Ocean anyways.  Anyone who suggested otherwise was labeled a hater.

Then came Winter.

Negative thirty degree weather reinvigorated their desire to make it west and they decided to move once the snow melted.

But Spring wasn’t so bad in this new place, and they already bought Lollapolooza tickets for the Summer, and the dope leaves came back in the Fall and then it was Winter again which meant it was almost Spring and you get the jist they never left.

Mike–back to the despair! We want despair!

It’s coming don’t worry.

Chicagoans mostly grew up in the Midwest, went to college in the Midwest, and make enough money to comfortably live in the Midwest. They dislike their jobs, but are happy with their living situation, proximity to family and friends, and the reasonably priced alcohol that warms their hearts and helps them forget.

And because their end goal is to fall in love and start a family, not create the next Google or Radiohead hahahhah what fucking simpletons am I right? ambivalence toward their jobs isn’t a huge issue.

Coasties tell you about their jobs before telling you their names. Jobs are about the tenth thing Chicagoans bring up. Their occupation isn’t their life, nor their route to happiness


it’s just something they begrudgingly do like taking out the trash or fingering your girlfriend after you cum.

Most Chicagoan college grads work in finance, logistics or sales. And when I say most I mean all.  My problem was–fucking finally, Mike— although jobs aren’t Midwesterners’ identity, they’re vital socially. I worked alone, so most of the time I was alone. Very alone.

I worked on shit I got paid for, shit I hope to eventually get paid for, and the rest of the day took long walks around the city, biked along the lake, or went to movies. I basically took myself on dates…and ALWAYS closed.

I’m serious about the dates, here are some photos:

unnamed (2)

“Saving Private Ryan 2: Intercourse Time” © Michael McClure Photography

unnamed (3)

“The Erect Pelican” © Michael McClure Photography

unnamed (1)

“HAGS” © Michael McClure Photography

They’re all incredibly metaphorical you just don’t get it.

If you want the full lonely experience listen to a Real Estate deep cut, get real close to those photos, and watch your happiness run to the bathroom real quick then never come back.

But don’t feel bad for me–dude, we weren’t–I was content being alone. It’s not like I was inviting people to come and they were declining.  The only thing that alarmed me was I was alone so much I started to prefer it.

Jesus Mike, enough with the despair, get back to Chicago 

Sports. Comedy. Bars. Blues. Segregation. 

What you don’t like Blues?

Jk lololololol yeah segregation is alive and well in Chicago. All the generalizations I made up there about young people are 100% true for 50% of the city. The south side of Chicago works like this:

Whites stay away from the south side–>

less money for local businesses–>

fewer jobs/lower property value—>

less money for schools–>

bad schools–>

kids drop out—>

kids join gangs/go to jail–>

come out but now DEFINITELY can’t get jobs but still have kids—>

turn to crime to support themselves/family–>

go back to jail (recidivism!)–>

their children grow up poor, unsupervised–>

their children drop out of shitty schools/ roam with violent gangs—>

white people stay away from the south side

This cycle isn’t exclusive to Chicago, but its proximity to white affluence is something that begs comparison to the Apartheid in South Africa.  Black people work on the north side mostly in the public sector, but most can’t afford to live there. Like a piece of lettuce between your date’s teeth, this issue goes largely unspoken.

So what happened Mike? More despair dude c’mon…

Okay, I wasn’t always lonely.  I went out every Friday and Saturday with old buddies who couldn’t have been more welcoming. I made new friends and rekindled old flings. Importantly, I also discovered it is possible to live in a major city without having a real job. I even managed a few of those elusive, coveted memories where even in the moment you realize you’re going to treasure this for a long time.

Okay Mike, so Chicago was all sunshine and blowjobs?

No. And that’s okay.

Life isn’t a greatest hits album, it’s Graduation with “Good Life” but also “Drunk and Hot Girls.”  That’s why those awful “Just be happy” quotes are so harmful, they set unreasonable expectations and end up making people feel bad, or even guilty for not being super fucking stoked all the time.

Back to my crafty metaphor, Chicago has it’s share of tracks that fall flat as did my time there.

But the Chicago metro is open all night, there are beaches with a lake you can actually swim in, parks that will force you to use the word “Gorgeous,” free concerts and street festivals, a bustling downtown, live comedy every night, cheap craft beers, lots of young people, and the bars are open until 5am on Saturdays.

And if that’s not enough, fuckhead, here’s a giant bean:


The rest is up to you.

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