“A year from now, where do you want to be?”

It was an earnest question. The man posing it was Reed Sandridge, a 36-year-old nonprofit exec who’d grown up in southern Pennsylvania. He sat across the table from Anthony Crawford, a Washington, D.C. native in his mid-50s who’d spent the last decade and a half sleeping on the streets.

Reed had first spotted Anthony two and half years earlier on a frigid February afternoon in 2010, bundled up in a layer of coats, hawking the Street Sense Media newspaper at the corner of 18th & M in downtown D.C. Reed, who’d been recently laid off from his job at the height of the economic crisis, approached Anthony and struck up a conversation. He learned that the money Anthony made from selling the newspaper was his only source of income; that Anthony had cycled through the prison system for most of his life before ending up homeless.

The conversation sparked an unlikely friendship and the pair began having lunch together every Tuesday. Reed accompanied Anthony to his numerous doctor’s appointments and helped manage a dizzying list of medications. Anthony began naming Reed as his next of kin on medical forms.

But two and half years after that first encounter, as the pair sat down at Au Bon Pain for their weekly lunch, Anthony was still sleeping on the streets.

“Where do you want to be a year from now?” Reed asked again, careful not to come off as preachy.

Anthony mulled the question for a bit, then raised his head and peered at his friend through the thick lenses of his glasses. Reed noticed a spark in his eyes.

“I want to be in an apartment,” Anthony responded. “My own apartment.”

That answer would launch the two men on a journey to get Anthony into housing that would test their friendship and forever bind them together.

All the while, Reed tracked their journey on a blog, AnthonyandMe.com. The following excerpts, which have been lightly edited for concision, tell their story.

November 27, 2012
This morning was our first meeting. We met for a couple of hours, started mapping out what we needed to accomplish to reach our goal and then setting up some basic working parameters for our project and defining some SMART goals (I can’t help it—I’m a businessman at the core) for each of us over the next year to help keep us on track. We agreed to meet every other Tuesday to review each other’s work.

 

January 29th, 2013
Friday I met up with Anthony and accompanied him on his visit to the doctor. He’s got some serious health challenges… The physician was alarmed at Anthony’s blood pressure readings. I know of at least two other occasions last year that they admitted him on the spot to the hospital. It saddens me to write this but I am afraid that without permanent housing he will not be able to make the kind of changes to his health and diet that he desperately needs and will not live much longer. “Doctor, I want to live another ten years,” he said with conviction as we sat in small examining room at George Washington Hospital. That would make Anthony 65, two years older than my mother when she died of heart disease.

February 4th, 2013
[After Reed encountered Anthony sleeping on the street on a particularly cold night.]

I got home, shed my many layers and climbed into my warm bed topped with a soft white feather down comforter. I struggled falling asleep… I lay in bed questioning whether I could really do anything to help Anthony. I felt like a hypocrite saying that I am trying to help him and yet I left him out in the cold last night. If a friend of mine would call me and say that he needed a place to stay for awhile, I would not hesitate a second to offer up my couch. But I feel like that is a line that I cannot cross with Anthony. And while I may be wrong on this, I feel he needs to have motivation to get him off the streets and if I put him up in my place then I am scared he won’t work as hard to change his situation.

I’m starting to discover how little I really do know about the problem of homelessness.

February 26th, 2013
I spoke to Anthony yesterday. He has two meetings set up now with two different organizations which hopefully can help him with housing and employment. This is good news—but I am hesitant to get overly enthusiastic until we have some real progress. And I am not sure what Anthony really wants deep down inside. I’m concerned that he has fallen accustomed to his life on the streets. It’s not easy, but it’s familiar.

March 12, 2013
It was shortly after 11 a.m. when I got the call. Anthony cancelled again. “Maybe next week,” he said, sounding sluggish and melancholy. “It’s nasty out there this morning and I’m just going to stay here at the Au Bon Pain and wait it out and maybe try to get some sleep.” I offered to meet him there at the french bakery, but he insisted that today was not a good day.

This is the first time since we have been working together that he has cancelled twice in a row. I offered to change my schedule and meet with him on Thursday but he preferred to wait until next week.

Something doesn’t seem right.

May 21, 2013
So there are several items to update you on. First, Anthony is doing well. We got some amazing news recently. He was approved to receive a small amount of government assistance to help him as we prepare to move him into housing. What? Housing for Anthony?!?! Well, while I have been away there have been some people who have been very busy trying to find housing for Anthony. And with this small supplemental income, I think it will put him in a great position to get into some low-income housing.

June 18, 2013
Anthony and our superstar outreach worker from Pathways to Housing went to meet with Catholic Charities. They operate a house that offers single room apartments. “I’d have keys to my own apartment, can come and go as I want. I’ll have my own bed!” His face twitched a bit and he shook his head in disbelief. “And, the room has a small refrigerator and a lamp.”

July 28, 2013

Anthony was so excited to finally get the keys to his own place. While his arms were tiring from carrying his housewarming gifts, he never mentioned it. He just smiled and laughed the entire way back to his new home. I helped him carry the items up the stairs and into his apartment. I had a meeting that I needed to get to but still had a few minutes left. I helped him make his bed and thought it must feel strange, but wonderful, for him to be tucking the sheet corners neatly under his mattress. He placed the pillow carefully in its case and laid it on the bed. I watched quietly as he stood there holding his hand on the pillow. I didn’t ask what he was thinking. I didn’t need to.

***

Reed’s blog posts don’t end there. He continued documenting the shared moments in his and Anthony’s lives: attending Anthony’s first hockey game (“Too much jumping around,” Anthony remembers with a laugh, “I was afraid someone was gonna knock me over”); sharing recipes (Reed: “I’ve never met anyone who puts honey on nachos”); hosting Anthony’s first ever birthday party (Anthony: “I had tears in my eyes”).

Anthony still sells the Street Sense Media newspaper at the same corner he first met Reed: 18th & M St. NW. Reed says it’s the type of connection he formed with Anthony that convinced him to eventually join the organization’s board of directors.

“It’s that bridging concept that’s so fascinating with what Street Sense Media is doing,” Reed says. “If you are a shelter or a soup kitchen, those rarely result in relationships being formed. What other organizations do you know that give people that gift? It’s really unique.”

Reed and Anthony still meet up for lunch every other week.