Ninety-five percent of Thanksgiving do-gooders have been entirely digital this year, asking me for wish lists or straight up donating money for homeless operations, but a few wanted practical street outreach experience and one lady got more than she bargained for.

I always take first-timers to the gnarlier neighborhoods, both as a crucible to see if they'll become a repeat volunteer and because those neighborhoods need all the services they can get. The volunteers who come back either lived rough when they were young and empathize, or are so cushioned by the cozy love of a middle class upbringing that they enjoy the work without the dread that they could be staring at their own future. Some don't come back, but at least leave with a deeper understanding of why the work is necessary.

But sometimes you get a complete washout. A well-heeled white couple reached out after hearing me speak at a neighborhood meeting and wanted to shadow me close to their condo, blocks from the concrete nexus of misery that was the jail, the Greyhound station, the subway bridge, and a strip club. I told them I'd arrive with a tub of prepackaged hygiene kits, protein bars, and bottled water, and they could watch me engage with homeless while they passed out goodies.

It didn't occur to me to warn them how to dress for street outreach (this happened before with city officials who entered tent cities in bespoke suits and Gucci watches), and I ignored their business casual until the husband started peppering me with questions about why the homeless lady on his doormat wouldn't trust him.

I looked up (I am 5'5). "Well, next time you may want to dress down. T-shirt and jeans. And also" further craning my neck to this stork of a man "you need to squat beside her. If I was a poor black lady sleeping on the sidewalk and a tall white dude in an Izod shirt was looming over me, I'd keep my mouth shut too."

I couldn't register his expression, clearly he didn't expect that answer, but I kept it friendly and suggested he be patient and offer the lady food or clean shirts whenever he saw her in order to build trust. He switched questions. "I hear about these public feeding laws, do you think feeding homeless in parks has any benefit or is it just making things worse?"

By this point we were in the thick of it. Everything reeked of urine and crack smoke and diesel fumes, the pandemic hollowing out downtown until the only people outside were the most crippled who couldn't climb into top bunk beds at the shelters. A female vet missing a foot crushed her beer can and tried, unsuccessfully, to throw herself out of her wheelchair into the non-existent traffic.

"You have to feed people," I said, angry at the question but mostly at the street that wouldn't improve with a tub full of free hotel soaps, "If you don't eat, you get depressed, and things can really spiral from there. I had four clients die this month. Food is cheap. You have. To feed. People."

This was all getting to the couple, but we were almost done and I wanted them to stay curious, when a young hooker spotted me across the street and rushed toward us.

She had been referred to a women's shelter the other day but never got directions, could we help? I mentally rubbed my hands, thinking what a great opportunity this would be to draw the volunteers into the process.

I pulled the volunteer woman aside. "This lady has a bed reserved. I'm going to call the shelter to confirm curfew times, but it might be a few minutes. She's clearly upset, can you stick by her and make small talk so she doesn't drift away?"

I take a few steps back to start the call, but not so far that I can't hear the white lady ask, "So why are you homeless?"

Boy she's lucky she didn't get punched.

Hooker: "Well, the dealers gave me crack rock when I stepped off the Greyhound bus two years ago and I've been sucking dick behind the courthouse ever since."

The white lady didn't really have a response for that besides "oh." and the hooker took it as a cue to keep going.

"Oh yeah," she said, not meaning to shock anyone, just telling her story, "I was living in a whorehouse down the street, the dealers set you up with six guys at a time and they pass you around like a bag of chips. They keep the supply coming, you never wanna leave. I lost my kids to DFCS, grandma got a restraining order on me, and I haven't slept all weekend cuz these psychos under the bridge wait for you to fall asleep."

I half-listened while futzing with the social worker on the other end of the line, horrified at her story and at the same time knowing that she didn't have to invent any of it.

I pocketed my phone. "Your bed was given away last night, but I have a sleeping bag, food, and I can drive you to a wooded camp where you can hide for a while."

She liked this idea, and while we searched for scrap paper to exchange phone numbers the white lady tapped my shoulder, visibly aged, and said, "I'm going home."  I never heard from her or her husband again.

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