The Thing About Being Homeless


I’ve been homeless for about two weeks now. The thing about being homeless is that it’s dehumanizing. Okay, wait. That’s a really dumb and obvious way to start this essay. …The thing about being homeless is that it’s dehumanizing, but you still retain the core of your essential personality, which is weird.

I remember, after I had been homeless for about a week, the first time that I stared through the window of a restaurant, looking jealously at people who were eating; people on dates, single men or groups of friends eating hamburgers and appetizers – all these delicious things that I couldn’t have. I stared through the window in a pressed-nose sort of way. At that moment, I felt like a cartoon of myself. “…Wait,” I said to myself. “Am I actually staring through the window of a restaurant, looking on jealously?” I felt like a joke. Like a joke version of myself. Specifically, I felt like a 1940s Warner Brothers cartoon caricature of a hobo — which is exactly the problem. Because I started to laugh at myself then. But being able to craft an obscure-funny-hipster reference in your brain is not of particular use when you’re homeless.

In fact, I’m terrible at being homeless. I keep being like, “So am I just supposed to sleep outside now? …Wha?” My brain actually goes “Wha?” This is also the problem. I am disassociated from my homelessness. I’m not owning it. I’m not accepting it.


How did I end up in this situation? Well, it’s a little hard to explain, but basically, some things went wrong. I currently live (illegally) in the basement of an international youth hostel on Amsterdam Avenue and 103rd street. I could be kicked out at any time, if someone actually notices me. This is trouble. This is not good. The week before this, I slept in the hallway of an apartment building. (My ex-girlfriend’s apartment building, unfortunately. This was not a good idea, but I didn’t want to do it. I had only just become homeless, and I was confused. I was like, “What am I supposed to do again now?” And after my ex kicked me out, the hallway was fairly conveniently located.)

I have some regrets.

For one thing, I regret majoring in English Literature. In my current travail, my ability to hold a stimulating conversation about, say, “Beowulf” is not as useful as my professors promised it would be. I should have majored in something else. For example, I could have majored in How to Sell Drugs, which I now suggest should be a course offering at all major universities. Selling Drugs, as far as I can tell, is how my fellow homeless people make slightly more money as homeless people than I manage to do. I don’t know how to Sell Drugs, and I wouldn’t even know how to Get Drugs, and Getting Drugs is really the necessary part of the equation, before you can sell them.

…I mean, if someone came up to me right now, and held a gun to my head, and said: “Get me drugs in 24 hours, Oliver, or you’re dead, do you understand me? …YOU’RE FUCKING DEAD.” — well, if that happened, I still wouldn’t know what to do. I guess I would hang out in the park, or go to a bar, and be like, “Does anyone anywhere know where any drugs are at?

I have no idea how to do any of these things.

So, that’s a regret.

I also regret getting in a fight with my ex-girlfriend, “Allison.” Yes, she was crazy. She was a crazy girl who would scream at me, say, for trying to IM my boss about my job. She was a crazy girl who went through my phone and my emails. She was a crazy girl who would scream and block the door when I tried to go to A.A. at night. …On the other hand, she was cute. Also, she had an apartment, which was really kind of crucial to me being quasi-homeless, instead of actually homeless.

So yes, I guess I shouldn’t have reacted to what she did. I really shouldn’t have said: “…You went through my phone?!! What the fuck is wrong with you?” What I should have said was: “Oh, ha ha. Going through my phone and reading all my emails again, I see. Well, we all have our little foibles, right? I mean, I never do that, but hey. You just never know in this crazy world, now do you? And you’re being so concerned and attentive! …By reading every private message that is ever sent to me like that. You deserve a reward, really. Take a load off. Can I massage your feet? How ’bout I bake us up a nice delicious apple pie?”

But I didn’t say that. Instead, I got mad at her. Whoops.


Another thing that I regret is my current choice of outfit. Really, if I could have chosen any outfit, it would not be the one that I’m currently wearing. But I didn’t know that my ex-girlfriend would kick me out, and I originally had more clothes in a backpack, but right now, they’re locked up in a locker, which will cost $5 to re-open, and I currently only have $16. Whoops. I had not planned on my current attire being my outfit forever, but now, it has to be.

But if I could do it all over again, I definitely wouldn’t go with the brown shirt with the tan scarf with the black hoodie combo that I have going on. Because the overall effect is… not flattering. It’s not good.


My ex-girlfriend still calls me — like nine times a day — but I’m confused as to why. She calls me up to moan about her job as a marketing executive, and she’s like: “So Sophia did this today, blah blah blah.” And then I’m all confused. I’m like, “But wait. Aren’t I homeless already? Can we focus on that? Sophia who? Do you realize that I slept on a bench last night? …WHAT IS HAPPENING HERE?”

The thing about being homeless is that it makes you very monomaniacal. You can only really focus on one thing; the inevitability of your current homelessness. Everything else is extraneous.  It’s like being in unrequited love for the first time when you’re sixteen; you can only focus on one thing. You can only drive around at night, thinking about your loved one and playing the same mix-tape over and over again. Except that, in this analogy, I don’t actually have a car, or a home, or a mix-tape.


The thing is, I’m just not very good at being homeless. But I’m getting slightly better at it. Instead of sleeping in the basement of the international youth hostel, I’m planning on locking myself in one of the shower stalls tonight. That way, I’ll actually have a door that closes, and I won’t be woken up by screaming hordes of German children at 5am, like I inevitably am when I sleep in the basement. …See?  I’m getting cleverer. You’d be proud of me.


This morning, I went outside and stood on the lawn of the international youth hostel on Amsterdam and 103rd Street, and I saw a bird. …And after this happened, I realized that I’m not just dumb about being homeless; I might just be dumb about everything.

There was a bird. It was on the ground. It was a brown bird; a sparrow, I guess. And it was rooting in the ground, and plucking up bunches of grass, and then it grabbed a random piece of string that was on the ground, and held all of this stuff in its beak.

I had never seen an avian creature do this before. And I was like, “What the fuck is wrong with this bird? Has it gone rabid or something? …The fuck?” And then it came to me… it was collecting pieces of grass to build a nest.

How can I pretend to be a writer; or even pretend to be anything, when I can’t even understand what is going on right in front of me?

It’s spring. The bird was building a nest.

It was a moment too obvious and dumb for metaphor; too obvious to be put down in writing, really. It was just another reminder that life is actually too dumb for irony.

The bird gathered itself on the ground for a second, and tensed its wings, then flew up, heading to wherever it lived so that it could build its new home.

And I thought: “I wish I could do that.”  Thought Catalog Logo Mark

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