4 Lessons Learned Infiltrating a Homeless Community

So, in one of his typical attempts to get me out of the office disguised as an article request, Cracked.com's Editor-in-Chief sent me out into the world on assignment to learn from the homeless.
4 Lessons Learned Infiltrating a Homeless Community

As of this writing, homelessness in America is at an all time high. We, as a society, are largely not OK with this, I've learned. So, in one of his typical attempts to get me out of the office disguised as an article request, Cracked.com's Editor-in-Chief sent me out into the world on assignment to learn from the homeless.

It wasn't hard to find homeless folks in Santa Monica, California. There was, in fact, a small, slightly organized community of wandering beggars just a few blocks from my office. I smoothly earned my way into their trust by offering them gifts.

"I have toilet paper," I said to the two gentlemen who were nearest to me. "Talk to me for 20 minutes and it's yours."

4 Lessons Learned Infiltrating a Homeless Community

"You a cop?" the first man asked.

"I guess you can say I police words. Or you could say I'm a journalist. You know what? Yeah, just say that, it's a lot clearer. You guys seem pretty homeless."

"That's fair to say."

"Great. I'm hoping to borrow some of your time for an article I'm writing about homelessness in America or, if this turns out to be a bust, dinosaurs in hats."

"Well," the first man said, "I'm Ernest, and this is Carl. You keep that toilet paper flowing and we'll tell you whatever you want to know."

"Or you can put sombreros on us and we'll pretend to be velociraptors," Carl chimed in.

"Yeah, either way."

This was going to be a piece of cake.

4 Lessons Learned Infiltrating a Homeless Community
Look at you, being fancy. Where you goin'?

Homeless Sexonomics

If the no research I had done to prepare for my stay in Homeless Country was any indication, the homeless, as a people, are a lot more animal-like in their sexually indiscriminate nature than their human counterparts. There is no complicated courtship process, no formal lines drawn regarding who belongs to whom, and no need for wooing anyone of the opposing gender. Sex just degenerates into a primal act designed to provide pleasure and whatever it is that women are supposed to get from sex. The dating scene at Great Mount Homeless should be a total orgiastic free-for-all, like sloppy, cursing, unshaven Olympic Village.

"So what's the dating pool like here, Ernest? Is it good or what? Feels like it would be pretty good."

"I'm actually married," Ernest said. "Few kids, too. My family stays at a shelter in Venice. The wife, she can't work becau-"

"So what's the dating pool like here, Ernest? Is it good or what?"

"...You should probably talk to Carl."

Dammit. I wasn't excited to talk to Carl. His shifty eyes and sly grin gave him an air of unreliability that he wore like a cape (which he also wore).

4 Lessons Learned Infiltrating a Homeless Community

While there was something deeply earnest about Ernest, Carl gave off a vibe of mischief, like he was holding onto a dark secret about you. Something personal that cut deep into your core, he kept it locked behind his cold dark eyes. I also I felt like I could taste poo just whenever I looked at him.

"Gimme straight-talk, Carl. If I'm going to be homeless for a while, what can I expect as far as ass-gettery goes? We talkin' 'loads' or what?"

"What? Right now?" Carl said. "In the middle of the day? Sure, I guess, how much you got?" He started unzipping his and, much more troublingly, my pants.

"Oh, no no no, there's been some terrible, Carl-shaped mistake. I just meant, like, what's the romantic scene like out here? Is everyone spoken for, or is it mostly dudes or is- Can you just focus on something that isn't my dick for a few minutes?"

"...I can promise to split my focus between your dick and this conversation. About 60:40."

"That is both agreeable and completely understandable."

"Living out here," Carl began, his focus still very junk-centric, "there's not a lot of room for relationships or casual sex or whatever. Everyone's always trying to make something in exchange for something else. No homeless chick is going to give up sex for free. Everything's got a price here."

"Huh," I said. "I really thought homelessness was going to be a step up from the general California dating scene."

"Oh, no, I'm just talking about sex in the homeless community. Being homeless is great when it comes to snagging non-homeless chicks. Any chick who wants to piss off her dad or get back at their boyfriend, they come straight here. This is, like, the peak of 'slumming it.'" And I thought my near-constant spitting and my perpetual lack of available T-shirts without armpit stains put me at the peak of slumming it.

4 Lessons Learned Infiltrating a Homeless Community
"Surprise! You're extinct."

"But with all of this anonymous sexing, aren't you worried about pregnancies?"

"Are you serious? What chick would admit to getting pregnant by a homeless guy?"

"Yeah, but still, even if you didn't have to raise the kid, wouldn't you be scared she'd sue you for alimony?" Carl blinked at me. "That sentence was stupid before I even thought it. You take care, Carl!"

Homeless Foodonomics

I was actually pretty excited about the dietary aspects of Homeless living. From what I could gather through daily observations, their food pyramid was largely alcohol and food-found-in-dumpsters-based. Alcohol and I are old friends, and as someone who often has trouble deciding what to order in restaurants, I looked forward to the "Every Meal's a Surprise" aspect of dumpster-diving.

"I guess coffee is really the only luxury I'll allow myself. Just something to help get me through the day," Ernest explained. "Mostly, we get food from soup kitchens and churches. We also, you know, make money panhandling. We can use that to buy the same food you buy."

"I can't believe we're not giving you shittier food... This is awful."

"Yeah, life must be pretty tough for you. We also occasionally get free food when bakeries are finished for the night. Krispy Kreme's pretty good about giving us leftover donuts when they close. It's either that or they toss 'em out."

"Unwanted. Despised and discarded. Like the baked goods version of you people."


4 Lessons Learned Infiltrating a Homeless Community
A stegosaurus cowboy? Now I've seen everything!

"Yeah. Hey, wait a second, shouldn't you be drunk right now? What gives? I thought you guys were supposed to be bums. When are we gonna start drinking our damn faces off?"

"I don't- You clearly haven't waited to start drinking."

"How do you mean?"

"You smell like booze, you're wobbly, you've been slurring your speech. You're holding a half-empty bottle of whiskey, currently, while we're talking, right now. Three-quarters-empty. Jesus Christ, man."

"Ah ha, now we're fucking homeless! Blaow!"

Homeless Moneyonomics

The Homeless Economy, as I suspected, was based on trading and begging. Homeless folks trade and sell what they have with other homeless folks and beg for money from non-homeless folks (or, "folks"). Ernest did fairly well in the trading community thanks to years of sales experience in his non-homeless life. By my estimation, he'd gotten a little rusty, his sellable items probably being the limiting factor.

"Come on, O'Brien, buy my pee."

"In a minute, Ernest. My boss sent me here for work, and if I come back with another jar of urine instead of a story again, he's not going to be too pleased. Tell me more about this homeless-bartering system you have."

Ernest sighed.

"It's just 'bartering system.' You don't have to qualify everything with 'homeless,' it's insulting," Ernest said, his homeless emotions pouring out, transient tears forming in his pale, bummy, crack-addicty eyes. "There are never any even trades exactly. It's tough to assign value when you're mostly dealing with meaningless scraps of garbage."

"Isn't that what money really is, Ernest?"

"No. Look, do you want to buy my pee, or what?"

"Is it clean?"

"Mostly no, but there's a lot of it." Born a salesman, die a salesman. I traded Ernest a necklace made of used Handy Snack sticks for a jar and a half of chartreuse urine. "It was a pleasure doing business with you, Ernest."

"I'm gonna flip these sticks in 45 minutes and you're going to feel like an asshole."

"I do not like them, Sam-I-Am. Rawr, roar, argh, eating-you-now!"

As happy as Ernest seemed to be with his stick bling, I couldn't help but feel sorry for him. Those sticks couldn't honestly feed his family; it's just not really a stick-buyer's market right now. And he did say that the bulk of his money came from panhandling but that's, what, a few quarters here and there? I was determined to straighten his life out.

"Why don't you just get a job? Something manual that requires little skill, I'm sure you can find something. I used to wash dishes for a living. It wasn't exactly glamorous but at least it's legit and, hell, it can't be any more depressing than begging, you know? And I think you'll find honest work to be really rewarding."

"I make upwards of $300 a day panhandling," Ernest said flatly. "And I'm not the only one."

"Oh, simple Ernest. Look, I know $300 a day may seem like a lot of money but holy fucking shit it totally is."

"Well I mean that's the biggest misconception. People see us and they think we're lazy, or unskilled, or too dumb to work or whatever. But we see you guys in suits, worrying about being late, filling out forms, like that's so much better. I don't know. I make good money just standing here asking for it. Sure there are some compromises, but isn't that true of every job and lifestyle choice? You look down on me for having to beg, that's fine. I look down on you for making less than me and having to pay taxes on it."

"Wait, there's... just give me... I'm sure there's a reason I'm in a better... Because I wouldn't be doing this job if..."

Quitting My Job and Becoming Leader of the Homeless Menonomics

OK, enough of this bullshit.

"Ernest," I said, tearing my clothes and pouring my recently purchased urine all over myself to get more of an authentic homeless vibe, "point me towards your homeless leader. Who's in charge, here?"

"In charge? Uh, I guess... Yeah, I guess King Steven would probably be it," Ernest said, indicating an older gentleman in the distance.

"Why is he your leader? Was there an election, like in that movie, or is there some kind of fight club thing going on, like how they make Prime Ministers?" Ernest shrugged.

"We just sort of collectively decided we needed a leader and, I don't know, Steve seemed to still have most of his shirt at the time." I looked to Steve's shirt.

4 Lessons Learned Infiltrating a Homeless Community

With one full sleeve, a urine stain and only a few burn holes, it did stand out from the rags the other homeless citizens were wearing; Ernest's shirt cut off around mid-man-titty and there was a giant hole in the back, and Carl's shirt was basically just a collar. "I mean, you can't tell now, but a year ago he had both sleeves, and the bird that currently lives in his back pocket hadn't quite settled in yet. I think it's a sparrow. This might all seem arbitrary to you, but-"

"No no, I can see how a second sleeve would command a lot of respect in your community. That's basically how we decide Congress back in the real world, if I'm remembering that correctly."

"It really bothers me that you're allowed to live in a house."

"I get that a lot. Listen, Ernest, you've been great, but I'm gonna go ahead and regicide the eff out of your boss over there."

I marched over to the one they called Steven, with a hard, throbbing confidence that could not be thwarted.

"Steven," I shouted fiercely. "It's me, Daniel," I added, less fiercely. Helpfully, even. In response, he simultaneously made a whistle and farting noise, which is either a really neat vocal trick or gross.

"Are you the one they call 'Steven'? The McMurphy to this Cuckoo's Nest of vagabonds?"

"Everyone is snakes," he yelled back.

"Couldn't agree more. I was wondering if I could bend your ear right quick."

Steven approached me with a mix of skepticism and peeing-himself. The live sparrow he clenched in his fist seemed annoyed. Or intrigued. Or fucking bird-like, I don't know, I can't read bird emotions. Steve spoke up.

"The government wants to harvest your droppings."

"I can see that. Sort of a legend in the bathroom. How long have you been doing this 'homeless' thing?"

Steve consulted the sparrow before speaking again.

"There's a button on my face that makes you feel my thoughts but I can't reach it."

"Isn't that always the way? So anyway I was thinking about challenging you for the throne. Thoughts on that?"If I could only get that sparrow away from him...

"You look like you'd make a fat president. Everybody bomb!" Steve was either crazy or freestyling at me. (Have you heard modern rap lately? It's really hard to tell anymore.) Either way, I was offended.

"Sir, your vicious insult on my character/sick, nasty rhymes will not stand. I shall defend my honor and win your crown/spit vicious word-dicks and rape your ear-ginas." Maybe he was playing crazy the whole time, or maybe I was finally speaking his language, but for the first time, Steve stood up and looked me in the eyes like what I'd said actually registered with him.

"So you've come for my crown."

"I have. That bird, too, if we're negotiating."

"Youthful ego. You didn't see me in my peak, you know."

"I heard about the sleeves."

"What makes you think you can handle my kingdom?"

I shrugged.

"I don't know. I'm usually pretty good at stuff I guess and got shit else to do. It's less about me knowing I can handle it and more just me wanting it. Plus your kingdom's, like, two blocks long."

Steve was shocked.

"You want this life?"

"Sure. You guys get free garbage donuts, you make money doing nothing, you get to poop wherever you want-"

"Is this the list of pros?"

"-you get to hang out with stray dogs and fly-ass sparrows all day. It's bullshit. Homelessness beats Capitalism every day of the week."

"What? Being homeless isn't better than Capitalism. The fact that we can survive off the excesses of Capitalism proves that the system works. And while there are a few surprising perks to this lifestyle, it is a tragedy. If you really wanted to be the 'king of the homeless,' you'd help us by doing something about this problem."

"I get a crown for that?"

"For eradicating homelessness? Yes, probably, I'm sure we could whip something up."

"Still kind of feels like a lot of work..."

"Yeah," King Steven said. "Well, that's what it takes."

"Huh. No deal," I said, loosening my pants. "I'm really digging this whole 'total freedom' thing you guys have going on, I think I'm gonna love it here."

"Just because you're homeless doesn't mean public masturbation is legal."


As I sit here in my pleasantly air conditioned, Southern Californian apartment, I'm reminded of just how cold this world can sometimes be to its own inhabitants. Discarding what it doesn't want without a second thought. People take pride when they perfect the art of stoically ignoring beggars they pass on the street, like it's a badge of honor to not have your gait disrupted even when someone tearfully pleads for whatever change you can spare. Well, just because we can't see them, doesn't mean they're gone...

4 Lessons Learned Infiltrating a Homeless Community
Never forget.

Scroll down for the next article
Forgot Password?