The Residentially Challenged

On August 15, 2011, at 7:25 p.m., I find myself holed up at a Lincoln Park Subway restaurant in Chicago, my phone charging behind the counter, with a Gucci duffel bag at my side and my Mac Book sitting in front of me.  I am, of course, stealing the Subway’s Wi-Fi and on that social networking black hole known as Facebook, but I am also currently homeless.  With a Gucci bag.  Homeless people, we are taught to believe, don’t own Gucci bags.  Nor do they own laptops.  Or so you would think, until I come bumming around to prove your ass wrong.

As I question where I will be sleeping that night, Lady Gaga’s “The Edge of Glory” comes on in the background.  On account of not having a place to stay, sleep, fuck or brush my teeth, I consider the song and somehow do NOT feel like I’m on the edge of glory.  Rather, I feel like I’m in the gay version of that Will Smith movie.  You know the one I’m talking about.  “The Pursuit of Happyness.”  It sucked.  But so does being homeless.  Oh, and PS to the producers of that shitty Will Smith movie, it’s spelled “happiness.”  God, not only did your movie suck, but so does your spelling.

However, since I’m one lucky son-of-a-bitch, a frat brother turned Chicagoan will soon contact me on Facebook chat, and let me know that he is about to go out of town for a week and I can house-sit his studio apartment for him.  I proceed to book it out of that Subway faster than an immigrant fleeing a Southern Californian tequila bar during a raid.

So how was it that I came to be homeless in Chicago?  Temporarily and fashionably homeless, but still homeless nonetheless?  Well, it all links back to when I moved to Chicago a year ago.  To keep an 11 month-long story short, I didn’t know what I was in for when I moved to the city.  As I discovered between the lovely months of October through April, The Windy City gives “Sarah Palin’s Alaska” a run for its money.  Because when winter hits, you too will quickly put aside any misgivings you might have about cruelty towards animals, proudly announce, “I love the rabbits.  But I love me more,” and don a ridiculous looking hat that insulates your head via rabbit fur.

In essence, I had my naïve dreams of living in The Big Windy Igloo dashed by winter and a three-day, record-setting blizzard in the no-man’s-land that is Chicago in January.  So, in an irrational case of delusional decision-making, I decided to move back to Florida.  This time, I set my sights on Miami.  Because who doesn’t want to live in Miami?  Or possibly because I’m a fool.

Suffice to say, Miami did not go well and during that glorious summer I lived the life of a “Nip/Tuck” character (I would like to imagine myself as Kimber).  In the span of two months I:

• Consumed an inhuman amount of the $3 bottles of wine available at Whole Foods.  Or, on the rough nights, Four Lokos.

•  Edured countless South Beach nightclubs, often accompanied by bathroom photo-shoots with my cheeky Latin friends.

• Threw a Lady Gaga themed party.  The costumes just made us look asinine.

• Entered and attempted to sabotage a gay club contest in order to win a free trip to New York City to get married to my former best friend and ex-boyfriend (who will from here on out be referred to as Trouble).  To explain, we weren’t really going to get married – obviously, if Rihanna and Chris Brown couldn’t make it work, we couldn’t either – and we came in second place, but only because the two unattractive douches next to us brought all their friends to cheer them on.  The contest was clearly fixed, because how we didn’t win when Trouble bit the garter off my leg and I threw it into the cheering crowd is beyond me.

• Drowned Trouble's white linen jacket in a canal after "a botched threesome."

• Was stalked and harassed in a South Beach parking garage, culminating in a car chase while my friend dialed 911 and I debated whether or not to swing my car into reverse and run the idiot over.

• Nearly broke my face on the ground while soaking wet after leaving a swimming pool at 6:37 in the morning.

• Paid approximately $837 in parking fees.

• Drove approximately 1,384 miles throughout Miami, Boca Raton, Fort Lauderdale and West Palm Beach.

• And had a miserable time as a South Floridian, because the heat is always sweltering, you have to change your clothes about six and half times a day, everything is expensive, and….well, have you ever been to South Florida?

With all of that in mind, suddenly the thought of Chicago didn't seem as bitter cold as the thought of waking up ten years from now in the depravity of South Florida and wondering where both my life and liver had gone.  I put aside my grievances with the Chicago transit, the weather, the fact that a fair percentage of Chicagoans seem to have a stick super-glued into their asses, and looked past the $2,000 my parents had paid to move me from Chicago to Miami.

I readied my baffling sense of entitlement (something that can be found in all gay boys’ DNA), picked up my iPhone, called the parents and I says, “O-hai, Miami isn’t working out.”  Okay, so maybe I pissed myself a little bit too while thinking of what their reaction might be.  To my surprise, they rather excitedly asked, “Does that mean you’re moving back to Chicago?”  I retorted, “Well, yes, but with your money.” (Just to emphasize exactly what a cartoon character I am, I didn’t have a job in Miami and still don’t have a job).

Within two weeks my bags were packed for Chicago and I left behind a group of rather pissed-off close friends from college.  These friends were understandably bewildered by my abrupt departure, and probably wondered exactly who the fuck I am and where I get the money to do such things.

[As a side note:  I don’t know the answer to those questions.  All I know is that I lead my life like a character out of a CW show.  That is not an admirable quality, I realize.  But I do believe I could truly substitute in as a long-lost stepbrother for Serena Van Der Woodsen on Gossip Girl.  Not because I have a trust fund, but because – somewhere in between seeing Cruel Intentions in the sixth grade and repeated viewings of Gossip Girl on my iPod while I worked out at the gym (yes, apparently gay men do watch Gossip Girl at the gym) – I got it into my head that I was a trust fund baby.  My father frequently describing himself as a golden parachute surely did not help matters, either.  I mean, let’s face it, “golden parachute”?  At that point you’re just egging me on to spend like I’m the offspring of Donald Trump and Nicholas Cage.]

When I arrived back in Chicago to enjoy the final two months of summer, my Chicago friends were kind enough to let me crash on their couches, eat their food, and generally annoy the piss out of them while I desperately searched for a place to live.  But because the kindness of my soul couldn’t bear to be an inconvenience (and, really, if you’ve ever seen me stumble home at 3:30 in the morning, you know just how much of an inconvenience it can be) I bounced around from friend to friend.  Kind of like an adult in custody; an adult who neither of the parents really want.

And on that fateful day of August 15, 2011, at 7:25 p.m., after homelessly navigating the mean streets of Michigan Avenue and Lincoln Park (say what you will, but the tourists and hipsters can be rather vicious), I find myself waiting for a friend to get off work so I can make the trek down to his place in Hyde Park.  We are not talking Barack and Michelle’s version of Hyde Park here, either.  That is a fantasy and is not what Hyde Park is like, don’t ever let yourself be duped into believing otherwise.

And that’s when my Facebook chat pops up and I am saved by my fraternity brother.  At least until winter.  Or, in actuality, until the end of August when I will discover and sign for an amazing studio in the Gold Coast with this here pretty view.  You see that, bitches?  That’s MINE.