The Reciprocity of Haight Street

[Note: This was a submission made to Longshot Magazine, a publication that gives writers 24 hours to write on one theme; in this case it was “debt”. It was quite the mad rush of interviewing and writing. Here is a PDF version if you’d prefer to read it that way.]

“It’s all in the approach.” That’s what I think to myself as I walk up Haight Street. You can ask anybody just about any question if you approach it the right way. I’ve been blessed (or damned) with a dry, baritone voice so my questions always come across as slightly more direct than intended. That, and the almost inescapably poignant nature of the question, will be working against me. I have the habit of getting into friendly but boisterous debates with random people, like cab drivers, but have learned to smother the poignancy of a debate, like questioning their union’s motives, without drawing anger.

So why shouldn’t I be able to have a conversation on a tense subject with a homeless person? My curiosity is honest. I really want to know the answer.

I do my best to remember this as I pass throngs of tourists. They’ve come to the famed ground zero of San Francisco’s Summer of Love, the hippie movement and Haight-Ashbury; a woman walks out of a store with a $30 tie-die shirt folded over her arm. Soon, through the crowd, I see a man with a clipboard moving from passerby to passerby. He approaches each person with a limp and his head low.

I slow my gait.

“ ‘Scuse me young man, can you spare some change for the homeless?”

“Sure. You mind if I ask a few questions too?” I ask.

“Of course,” he says, almost stately.

His name is Mark. I notice that Mark’s left eye doesn’t open. There are other scars across his face, but no swelling or open wounds. Just divots from a tough life. I ask him about the program outlined on his clipboard; he gives me the breakdown of how my five dollars just funded a week’s worth of meals for someone; not to mention, it netted him $1.20. I ask him how long he’s been homeless and he proudly tells me that he’s been “on the street” for three years now.

“Do you drink?” I ask.

“Sure I like a drink now and then; I won’t lie. What, you don’t?” Mark doesn’t get angry, but he’s certainly heard the question before.

We talk about his shelter and donations, and finally I wind around to my question. “So, in your own words, Mark”—I’d decided on this preamble to soften the directness— “Why should people give you their money?”

A moment passes.

Through one eye, Mark sizes me up and decides I’ve asked a simple question. He taps his clipboard. “You helping someone, man. Why you think?” He nods across the street. Three rosy-cheeked teenagers sit on the sidewalk; one smokes a joint as another asks a passerby for spare change. “Them boys, like that, they ruin it for the rest of us. Ruin it. I’m trying to make something happen. I wear a tie every day. I don’t know what they doin’.”

We talk a moment longer and soon I say goodbye; almost before we’re done shaking hands Mark shows a Japanese couple his clipboard and asks if they can spare change for the homeless. They decline. I realize that I didn’t think to ask how many five-dollar donations he gets in a day; and in turn, how many $1.20 commissions he pockets.


When I’d left for Haight Street that evening, my girlfriend had told me to “be careful.” Though, I wasn’t worried. Haight Street is crawling with policemen and most of the homeless, unless they are too far out, keep the peace. They occasionally yell something obscene but usually just ask passerbys for money. That’s really it.

But the fact that the question of “why should I”—without “Get a job!” underneath—should induce a tense moment, perturbs me. Most anyone I know would look at me tentatively if I told them what I was doing. A trap seems to ensnare us into believing discussing homelessness is inherently haughty. If you live a reasonably comfortable life, how you can you ask questions of, in any way, someone sleeping in an ally without coming off as judgmental—even if you are truly curios? We’ve instituted a standard where you’re supposed to fork over the money, if you so choose, and keep moving. But someone is asking for money; why shouldn’t I request honest reasoning? Asking “why” is the one question we should always be allowed to pose; it’s the root of getting a handle on what’s around us.

I go less than a block before coming upon a girl sitting against a stoop. A big bull terrier, reminiscent of Spud McKenzie, lays next to here.

“Spare change,” she asks me.

She takes my dollar with a hand inked in letters of a strange alphabet; I can see the end of a tattoo sleeve on her right arm. With the deftness of a magician, she makes the bill disappear within the folds of her jacket.

“Mind if I ask you something?” I say.

She shrugs and asks, “spare change?” of someone behind me.

Her name is Maggie and her dog is Chance; Maggie took ownership of her about a year ago. I wonder, to myself, if the United States is the only country so wealthy that homeless people can often care for dogs.

“How long you been here?”


“On the—”

“Spare change?” she asks a passerby over my shoulder. “On the streets? Three years.”

A passing suspicion warns me that this is a standard reply, but I chalk it up to coincidence. “What were you doing before you—”

“Hi Paul,” Maggie says sweetly; girlie echoes drift through the weeds of her smoky voice.

Paul cannot weigh more than a hundred pounds. His denim jacket and pants are covered in buttons with ironic slogans. “H-hi, hi M-Maggie,” he says and they discuss an upcoming festival nearby and the free food. Paul shifts as he talks, as if he had bad blisters on both feet. His jaw is soft, if not deteriorating. He takes no interest in me.

“He local as well?” I ask after he moves on.

“Yeah, he usually stays just— Spare change?” The passerby gestures helplessly at his pockets and keeps walking and Maggie asks someone else.

“How many people pass by in a day?” I ask, nodding with a little friendly contempt at the guy who’d claimed empty pockets.

“I dunno. Lots.”

“Let me ask you, in your own words, why should people—”

“Hi Seven Trees! Long time no see, man!” The girlie echoes are back in her voice. Seven Trees has the shakes in both hands and struggles to steady a backpack. I decide I’ve worn out my welcome and say goodbye to Maggie. She doesn’t look at me as I leave. Part of me wonders if Mark would claim Maggie is ruining it for him too.


I try to talk to a few more people: Eye contact hinges on the financial request; I donate a dollar; then my timer counts down from ten seconds before I’m being ignored. Money is my icebreaker, but it doesn’t get me anything after. My hopes of an honest, non-contemptuous approach to gain mileage and a few moments of honest discourse begin to seem hollow.

Appropriately, ironically, at the next block I meet Be Serious. (He got tired of “the name the government gave” him.) His just arrived in San Francisco from Seattle and tells me further questions cost a dollar. I donate enough that I’m given leniency to ask a few extras. He is older and with the leather face of man that’s slept on a lot of sidewalks.

“So let me ask you, Be Serious,” I say when I think I’m on my last question before having to pay again. “Why should people give you money?”

He doesn’t flinch; Be Serious is raising money to buy a bag of pot for a dying friend. “Man’s never had a good joint in his life!” The reason he made his way down to the Bay Area is for the San Francisco Homeward Bound Program. Provided they have some proof of friends or family at the destination, the program provides the homeless with a bus ticket out of town. Be Serious plans to visit his childhood friend in Philadelphia and deliver the green goods. Then he plans to “put two crystals on my parent’s graves.” Why crystals? “Just because. One on each.”

I give him a couple extra dollars, shake his hand and decide I don’t care if he’s lying. I’m unsure what Mark would think about Be Serious’s story.


A kid in broken jeans and a black hoodie whispers, “Nuggets, shrooms, LSD,” as he passes me. I don’t acknowledge. The crowds, as I reach the west end of Haight Street near Golden Gate Park are starting to thicken and such clandestine narcotic offers are coming more frequently.

I duck into one of my favorite bookstores for a quick break, browsing blurbs and scanning chapters. I eventually notice Andrew Moore’s coffee table book in the corner, Detroit Disassembled.

Rich photographs of broken warehouses, abandoned gymnasiums, collapsing factories and displaced residents of Highland Park and Detroit’s East Side in front of their boarded homes fill the pages. I turn the book over: $50 even.


I need to break a ten if I’m going to keep talking to people. I walk a block, past a man laying on the sidewalk listening to the Giants game on a handheld radio, and into an empty convenience store. Wheel of Fortune is on an old 14-inch television overhead as I approach the register. “Can’t access the cash unless you buy something,” the counterman says. I know this isn’t true, but grab a Cadbury egg and pay. As I’m putting my change away, the man with the Giants game on the handheld, who’d been laying on the sidewalk, sets a drink on the counter.

“I’ll get his too,” I say, hoping for an opportunity to strike up a conversation. He glances at me, then he turns away.

The counterman looks at him with disdain. “This nice man bought your drink. And you will not say anything—Jamie?” As the counterman bags the can, what I thought was just an energy drink displays “12 ABV” near the rim.

“Last week…we had a bag and it had nine thousand in it…and nine thousand,” Jamie says, his hand shaking as he grabs the drink. He limps past me with his radio and continues muttering “nine thousand.” Sounds like the Giants are going into extra innings.

I exit behind Jamie and start wondering what frustrates me more; that I just purchased alcohol for a derelict; that I won’t get a coherent moment to talk to him; or that, all in all, my question of “Why should someone give you money?” is starting to seem stupidly “N/A.” The thought of no tangible answer to “why” begins to gnaw at me; there must be something, a general feeling. Even people like Mark, who are working to make their money, and those like Maggie who are simply asking for it, must have some cohesive thread to their reasoning. Their day consists of extracting a perceived societal debt; what ties it together?

In my head, I see two parallel planes. They slide past one another with a single contact point; the coefficient of friction is “sure, here you go” or a helpless shrug towards the pockets. That’s it. The interaction is binary and the reasoning, on either side of the plane is irrelevant; “why” is irrelevant, both for receiving—and giving. The transaction just happens or it doesn’t—and as often happens when something is boiled to the bones, it takes on the aura, not of hippies and homeless, but something far more brutally survivalist.


The end of Haight Street, perhaps perfectly, is capped with a Whole Foods and a McDonalds on either side. A woman with a cashmere sweater and knee-high leather boots, walks her German Sheppard into the Whole Foods parking lot. She ties him up near a sign that advertises Coho salmon at $8.99 per pound and heads inside. I debate getting something myself, but instead cross over to McDonalds’ side of the street.

The questions from those sitting on the ground has changed now, noticeably. What had been a low rumbling of drug offers is now a full symphony. They make it abundantly clear exactly why people should give them their money.

“Buds, Nuggets, Shrooms, LSD, Medication?”

Everyone is making eye contact. Everyone is up front, in your face, not shy. Young girls, who look they’re breaking daddy’s heart, stand nearby watching the exchanges. I overhear one aggravated dealer say to another, “Come to San Francisco and see it all. If they don’t like it, they can go back where they fucking came from!”

I’ve strayed from where I want to be, the areas not crowded with drug dealers, and begin back down Haight Street.

“Find what you’re looking for, man?”

I realize that the aggravated dealer, with his nuanced anti-tourist stance, was talking about me; now he’s talking to me.

“Yeah, thank you,” I say.

“Okay, have a nice evening.” His tone says fuck you.

I wish him a nice evening as well.


I see Maggie again; she’s moved, likely having been told to vacate the stoop she was in front of. A second dog has come over to play with Chance and Maggie is feeding it. “Hey Maggie,” I say.

She stares back at me without a hint of recognition. I smile, and still nothing from Maggie.

I soon see Jamie, still with Giants on the radio and my drink in hand. He paces back and forth, aimlessly, in front of a store that sells t-shirts advertising “Darth Vader for President” and other such ironic slogans.

I send my eyes downward and begin walking swiftly, avoiding any and all interactions.

“Excuse me, do you have a moment for Planned Parenthood?” a girl with a clipboard asks sweetly.

I look up, startled, “Sure” and ask reactively, “Why should people give you money?”

She flinches at my directness. “We’re out to raise money, because the Congress is passing new laws that will shut down clinics. So we want to stop it. Minnesota has had twenty-seven of twenty-eight…”

I listen to her blankly until she finishes. “So how do I donate?” I ask.

She folds over the pamphlets on her clipboard and reveals a gigantic payment form with home address, email and credit card information. “You’d start by filling—”

“Can I just give you some money?”

“Sorry, we can’t accept cash.”


“No. We need to capture your information with this form.”

“I’ll do it online when I get home.”

“Okay, have a nice day.”

3 Responses to The Reciprocity of Haight Street

  1. Nancy says:

    Such an interesting and compelling blog.

  2. Gyan says:

    Thanks for writing about this Caleb. I’ve asked that question once or twice over the years and never received much of an answer either. Really enjoying these posts…keep ’em comin’!

  3. John says:

    That was great, Caleb – interesting, engaging, and colorful. Nice job!

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