I met Olivia Wynkoop, a sophomore at San Francisco State University, on Feb. 3 in a journalism class. I’d been invited to share reporting techniques, and I talked about covering homeless and underprivileged communities in the East Bay.

I told the students that reporting on homelessness must include the voices of the homeless. That means engaging people living on the streets and getting to know their names and stories.

Many of us are so privileged that support — physical, mental or financial — is just a phone call away. Shouldn’t we use our privilege to help the less fortunate?

Wynkoop, 19, took my words to heart.

On Feb. 4, she took a homeless man shopping after meeting him on Muni. But the gesture left her furious, and not because of anything Gabriel did.

She was upset by how the employees and shoppers reacted to seeing her shopping with a homeless person.

“Security came up to ask me if I was OK as if there wasn’t a man beside me who was deprived of the basic needs we often take for granted,” she wrote me in the email the same night. “I would see people avoid him in aisles and gawk at him like he was a spectacle.”

Her words put a lump in my throat. The last time an email similarly affected me was in May 2018, when Barbara Lustig called me out about male entitlement. Lustig and I still keep in touch.

Wynkoop said she was aware of the stigma associated with homelessness, but she didn’t have a sense of what it felt like to be shunned until she walked beside Gabriel.

“I’m so thankful I could use my privilege as a ‘normal’ looking, white, female college student to advocate for what he needed in the store,” she wrote. “Without me next to him, I’m afraid that his needs would be dismissed as a threat.”

I wanted to hear more about her experience, so we met for brunch in the Castro. Wynkoop is from Dixon, a small Solano County city. She said she wants to be a journalist. The incident cemented career plans.

It was around 8 p.m. on Feb. 4 when Gabriel and another homeless man got on Muni at Civic Center. Wynkoop saw Gabriel’s side was bandaged under his T-shirt. She offered her seat, and Gabriel began writing in a notebook.

“The whole time I was really reflecting on what you talked about in class,” said Wynkoop, who often writes when she’s lost in her thoughts on Muni.

Gabriel asked Wynkoop for directions to Target. There’s a Muni stop in front of Stonestown Galleria, where there’s a Target.

Wynkoop said Gabriel told her he was surprised she wasn’t afraid to talk to him. He was with another man, whom he said he’d met only two days before. Wynkoop said she didn’t speak to the other man who sat down inside the store as she and Gabriel shopped.

Gabriel’s T-shirt and sweatpants were filthy. His steps were labored. He was worried security was going to kick him out.

Wynkoop said a security guard and two employees shadowed them even after she made it clear that they were together.

“I feel it’s so easy to criminalize and villainize people just based on the way they look,” Wynkoop said. “People don’t deserve to be treated that way.”

But that’s exactly what we’re conditioned do in this country, whether the status is about race, immigration or housing.

Gabriel selected the cheapest sweatpants he could find, but Wynkoop didn’t think they were thick enough. She chose a more expensive pair. She bought sweatpants, eight pairs of socks and groceries. She spent $60, which includes the $20 she gave Gabriel as they parted ways.

Her mother called. They talked about the experience, and her mother asked how she was feeling. Wynkoop said the question made her cry. As she recounted the conversation, the tears returned.

“It’s just really not fair,” she said. “I just got this incredible feeling of guilt.”

She wondered whether she did enough to help. In her email, she asked whether covering homelessness affects me.

“Can it drain you emotionally and tax your well-being, despite how much good you’re doing in the process?” she wrote. “What advice would you give to help ease this feeling?”

Oh, there isn’t a day that I’m not pained by what I see on our streets. But I didn’t know how to ease Wynkoop’s guilt, so I called Thomas Plante, a professor of psychology at Santa Clara University.

To foster community solidarity, every student at Santa Clara University, regardless of major, has to take what’s called an Experiential Learning for Social Justice course. Plante’s students spend two hours a week at Julian Street Inn, a San Jose shelter that provides emergency and transitional housing for adults coping with homelessness and mental illness.

He told me guilt can be productive.

“We should feel guilty when we’re running around San Francisco and the Bay Area and walking over a person laying on the street in order to get our $5 latte,” he said. “If guilt can help us to continue to humanize folk, that’s a good thing.

“If it motivates us to pressure our politicians or our hyper-rich billionaires in the community to help, that’s a good thing.”

We’ve trained ourselves to look past homelessness until someone gets on public transportation, sets up a place to sleep in our neighborhoods or walks into a store.

“How is it just so much easier to just walk away from someone than finally see people as people and try to help them out?” Wynkoop asked me at lunch.

That’s exactly what I’m trying to figure out.

San Francisco Chronicle columnist Otis R. Taylor Jr. appears Mondays and Thursdays. Email: otaylor@sfchronicle.com Twitter: @otisrtaylorjr