It’s 11 p.m. in Downtown Crossing last Wednesday night— a night so cold it punishes every bit of exposed skin. Boston Mayor Marty Walsh leans down to speak to a woman huddled in a corner outside a store.

“Why don’t you come in? It’s too cold tonight.” A few blocks away, she can find shelter at the New England Center and Home for Veterans.

The woman looks at the mayor with large frightened eyes — she says she doesn’t want to lose her freedom. Walsh tries to reassure her: “You’re gonna have your freedom tomorrow — come in tonight.”

The woman declines again, and the mayor instead offers her some blankets.

This reluctance to accept help presents a common predicament for the 300 or so volunteers who are part of the city’s census of homeless people, which has taken place annually for the last 39 years.

Jim Greene, the city’s point person on homelessness, has been doing the census for more than three decades. The night’s count, he says, was far and away the highest count he’s experienced.

That night, as he approaches people, Greene tells those who are reluctant that six people died the night before on the streets of Chicago.

“It’s gonna be 30 below,” he warns one person, adding that volunteers can take the person to a shelter in a van.

Persistence is key, Greene says — just keep offering to help more times than the person rejects your offers.

Greene stands outside the 7-Eleven, where several people struggling with homelessness walk in and out.

“We are fully covering the area. That was six or seven people emerging, and the priority was, let’s get people into shelter,” he says. “So far, five out of the seven took a ride to shelter. Somebody’s going to an ATM machine around the corner, and the other gentleman went to an ATM machine up the way. At least those are heated locations, but we’ll have vans out throughout the night checking on people.”

Last year, the city reported 163 people were living without shelter — 23 fewer than the year before.

Those individuals are just part of the more than 6,000 people dealing with homelessness in Boston. They’re either living on the streets, or in shelters and transitional housing. 

This segment aired on WBUR 90.9FM on January 31. The Reporter and WBUR have a partnership and share stories and resources.