Shawn Grady, 44, lived in a sub-Saharan village in Africa for nearly three years with almost no money, but said it’s more difficult to be homeless in Boston.

Misfortune was anticipated in Africa, Grady said, and he did have a support system of nearby fellow Peace Corps volunteers. But Boston is more confrontational, even with it’s civic-mindedness.

“[Boston’s] sense of charity has to have a certain propriety,” Grady said. “And if the need bleeds out of those parameters, well, they’re kind of stymied.”

Grady’s experience was amplified this winter, after the Long Island Shelter closed in October. In December, the U.S. Conference of Mayors released a report that said Boston has the largest emergency shelter population of 25 major U.S. cities. The city’s resources were then strained further by record-breaking snow. Grady had stayed at Long Island last spring, but that option was suddenly closed off after the bridge connecting the shelter to the mainland was condemned.

“I think this was the Mayor’s first big test,” Grady said. “And I don’t know the political variables of it, but people are miffed that he hasn’t been a little more high profile.”

Didi Gilbert, 29, had never stayed at the Long Island shelter himself, but has become cynical of the ways the city is helping its homeless residents.

“The Bible says to help the poor, because it’s the right thing to do, but governments do not help the poor because it’s noble,” Gilbert said. “They do it because it affects other people. But it will be warm in April, and then people will forget [about the homeless].”

This is Gilbert’s first winter without a home, and though he said that there is “no etiquette to being in destitution,” he tries to be grateful for any help he’s received. He said he’s worked in soup kitchens and group homes before, but now that he’s on the other side of the situation, he realizes he took a lot of things for granted.

“There’s this weird bureaucracy that turns everything into an obstacle course,” Gilbert said of the way homeless care is structured. “You wake up one place, then you have to leave, then you go somewhere to be warm, then somewhere else for food.”

The cold is always expected, both Grady and Gilbert said, but the snow is what makes things difficult. When you can’t lie down in the grass or sit on a park bench, you’re left to continuously wander while carrying all of your possessions.

Then you’re sleep deprived, stressed, and slipping on the ice, Grady said, and self-conscious of how others perceive you.

“Even waking up [in the winter] is not the same experience — you think about how many things you have to do before you can’t do them anymore,” Gilbert said. “It’s getting really hard not to stick out like a sore thumb, and I miss the days when we were invisible.”

Gilbert said no one plans to be in this situation, but it takes time, energy, and resources to get yourself out of it. In this weather, he’s spending all his time and energy dealing with the environment.

Boston Warm offers a reprieve from that onslaught. It’s a day center that runs out of Old South Church and was started by a coalition of local church members who wanted to respond to the Long Island closing.

“In this weather, you don’t have the same spots to go to as the summer,” Grady said. “And [going to Boston Warm] helps chop up the day, because you only feel so agreeable sitting in a hotel lobby for so long.”

Grady has been visiting Boston Warm for the past three weeks, after he met a buddy in the Prudential Center who told him about it. The two aren’t close enough to know each other’s names or where they often stay, but they see each other around. This community aspect is an important way to share resources they’ve learned about, Grady said.

Gilbert stumbled across Boston Warm because he goes to the Boston Public Library often, and the sandwich board that shows the shelter’s hours sits across from the BPL’s entrance on Boylston Street.

“I love to go to libraries in general, and I always have, but it hasn’t been lost on me that libraries tend to be a place to go for those that don’t have anywhere else,” Gilbert said.

Gilbert can tell when he isn’t welcomed, he said. He often gets glares for staying at a cafe too long without buying anything, or “bad vibes” from an over-crowded shelter.

“It comes and goes, and you learn when to be there and for what, so you can minimize the negativity of your environment,” Gilbert said.

Kate Layzer, director of the Boston Warm center at Old South Church, said that the day center has few rules but to ensure respect, in a system where other shelters “don’t always run on empathy.”

“We have just been bursting at the seams,” Layzer said. “And there are always pent-up tensions [in tight spaces], but our thing is about community, and an atmosphere of peace.”

Boston Warm was originally set to operate until March 31, but Layzer said that they are keeping the shelter open until the end of April. By then, she said, the urgency of escaping the cold will be less.

For Gilbert, who said you always hear about how hard times bring out the best in people, Boston Warm and other shelters like Pine Street Inn and St. Francis House have far exceeded his expectations.

“Boston does have options, but you have to be informed, and sometimes I feel sheepish asking for help,” Grady said. “But this is a season, and I refuse to let people pin me for my current situation.”

Appeared on Boston.com