"THE ABSOLUTE WORST that can happen is we'll both be stabbed to death."

We were having a strategy meeting over a plate of spicy beef at the Republic Café in Chinatown, and Patrick Nolen wasn't exactly soothing my fears. It was the Thursday night before I would spend the worst night of the year sleeping on Portland's streets.

Nolen, who works for Sisters of the Road as a homeless advocate (and who was himself homeless for eight years, until 2005), suggested in early January that I join him in sleeping out on the streets—to give our readers more insight into what it's like being homeless in the "City that Works."

"But let's do it in April," he'd said. "It's easier when things get a bit warmer."

Well, nobody calls me a wimp. Sunday, February 10, is known around town as "the worst day of year"—so I knew there was only one night we could do it.

In retrospect, having slept outside for just one night, I know I wouldn't last a week on the streets. Now I know that being homeless in Portland requires a certain kind of strength. There's room elsewhere to debate what needs to be done to help the homeless—but before you go making assumptions about what it's like, or pronouncements on how to solve the "problem," I'd suggest you do what I did, and try being homeless for yourself.

DRESSED FOR SUCCESS

Luckily, the Worst Day of the Year™ was not, in fact, the worst day of the year. Sun peeked through patchy clouds by mid-morning and at one point in the afternoon, the temperature touched 55. Nevertheless, at 5 pm I showed up to meet Nolen in downtown's O'Bryant Square, wearing two pairs of socks, long underwear under thick jeans, and three T-shirts under a hooded sweatshirt underneath my thickest black coat. Also: a beanie hat and thick gloves, for good measure.

Nolen showed up in shorts.

"I half-expected a phone call saying you weren't coming," he grinned.

Never mind that... what the hell was he doing in a pair of shorts?

"It's not that cold," he shrugged.

A repeating refrain of "WIMP" circulated in my brain, as I told him: "Let's just get on with it...."

FREEDOM! (IT AIN'T FREE)

"Homelessness, in many ways, is a very liberating experience," Nolen told me, as we wandered down to the Willamette River. "The only thing that matters is your survival and the ways you achieve it."

With no cash in my pockets and just a water bottle, an empty Tupperware box (for any leftovers), and a heavy blanket filling my backpack, all that mattered now was the basics: finding food, having somewhere to go to the bathroom, locating a sleeping spot, and staying healthy. Fortunately, Nolen had already bummed some pork-fried rice from a benevolent Chinese couple an hour earlier, at Potluck in the Park—a weekly Sunday homeless feed in O'Bryant Square. There were also assorted packets of nuts and a protein bar from LA Weight Loss Center, so dinner was taken care of. However, as the temperature dipped slightly, and an orange Lamborghini drove past us on Naito, I suddenly began to feel not quite as "liberated" as I would like—regardless of what Nolen may have said.

THE SLIPPERY SLOPE

For Nolen, the road to homelessness began in 1992 after dropping out of a business administration program at Clackamas Community College.

"I just realized I didn't want to be there," he said.

Nolen doesn't have much insight into what, exactly, caused his homelessness. Although he did lead what he admits was a fairly rootless childhood with his mother and a series of ex-military stepfathers.

"But I've never been one to blame things on people," he said. "I hold responsibility."

After college, Nolen bounced from "crappy job to crappy job," spending nights living in his car and on friends' couches over the next five years until he burned through most of his favors.

The first night he spent on the streets was outside the Royal Family Ginseng building on NW 4th and Davis—waking up to a junkie who was shooting up "right on top" of him. The second night, he slept underneath the Burnside Bridge, 'til the police moved him along (camping out in Portland remains illegal, even though there's a six- to eight-week waiting list for most of the city's shelters). The third night, Nolen can't remember much—he was too tired. After bouncing in and out of supported housing for another three years, Nolen began his longest stretch of uninterrupted street sleeping in 2000.

"I stopped going to shelters when I saw the guy in front of me in line get stabbed during a fight," he says.

So he slept on the steps outside the Keller Auditorium, opposite the headquarters of the Portland Business Alliance, on the corner of SW 2nd and Market.

For five years.

FILLING THE DAYS

"Being homeless is often a case of 'hurry up and wait,'" Nolen says to me, as we sit on a bench in Waterfront Park. "When I used to eat at the Union Gospel Mission I used to be in line by three, even though they don't start feeding until five o'clock. But what else are you going to do?"

Where most people fill homelessness with drugs or an alcohol addiction, Nolen admits: "I ate."

Prior to graduating from Canby High School in 1989, Nolen was a good wrestler and among the top 10 soccer defenders in Oregon for his age at 16. He weighed 168 pounds at the time. Now, he weighs more than 250. He was diagnosed with type two diabetes six months ago.

Nolen also spent his time reading—about 250 books in the last year he was homeless, everything from military history to politics to religion to science fiction. He would go into Powell's and read one inside. Or borrow books from his father, a retired Teamster, who lives with Nolen's stepmother in a house in Beaver Creek, an hour and 20 minutes southeast of Portland.

In the entire time he was on the streets, Nolan never told his father he was homeless, and they only started talking about it last month.

"There was nothing he could have done about it," Nolen says. "And I didn't want him to worry about it. He could have given me a little money and I'd have stayed in a place for a month or two... but then I'd have been right back on the streets."

NOBODY LOVES YOU (WHEN YOU'RE DOWN AND OUT)

Having no money and no home may be piss boring, but you can't just fall asleep and forget about it.

"If you're asleep before 11 [pm], the cops will roust you," Nolen said to me. "And if you're still asleep after six in the morning, they'll roust you then, too."

Which meant we spent the rest of the evening walking round the city. At 7 pm, we found the public restroom locked at NW Davis and Naito. That would be the same restroom that's supposed to be open, according to the mayor's Street Access for Everyone committee. This is the same committee that made it illegal, last August, to sit or lie on the streets between 7 am and 9 pm, in exchange for offering benches, showers, and restrooms (like the one that was now locked). Still, we both needed the restroom, so we snuck into Backspace on NW 5th instead.

At 9:30 pm, we swung past the Julia West House—a day and night shelter for the homeless—on SW 13th and Alder. A sign on the door read, "Showers closed until further notice"—even though the center is supposed to be offering those as part of the mayor's sit-lie deal, too. Inside, a priest appeared to be delivering a sermon of some kind, which put me off all thoughts of entry—even though it would be warm.

At 10 pm, Nolen showed me a sign outside the First Baptist Church on SW 11th and Taylor, saying the following in bright red letters: "No loitering. Church business only. Police enforced."

Behind the church's locked metal gate—confirming there'd be no sleeping in this doorway—there was also a drinking fountain, with an inscription from the prophet Isaiah, reading: "Ho, everyone that thirsteth, come ye to the waters. And he that hath no money; come... without money, and without price."

Nolen told me such apparent contradictions aren't unusual.

BROKEN SLEEP

Eventually we decided to sleep in Nolen's old spot outside the Keller. For bedding, I laid out flattened cardboard boxes we'd "borrowed" from the recycling bins of a nearby steakhouse. Earlier in their careers, my boxes had contained Chablis and cheesecake—which I tried not to think about... but I couldn't help it. Nolen said that one morning when he'd slept here, he was woken up with a boot in the head, which slammed his skull into the wall, knocking him out again.

"The next thing I remember, I was sitting on my bag about two blocks away," he said, estimating that more than 40 percent of homeless in Portland have experienced concussions as a result of being kicked in the head while sleeping.

Needless to say, I slept with one eye open. Well, actually, I didn't sleep much at all. While Nolen was snoring up a storm within 10 minutes, I tried hard to stop thinking of all the marauding bastards about to kick, beat, or stab me, and woke up every hour.

At two in the morning it was really rather cold, to put it bluntly. So I popped open the two Little Hotties hand warmers Nolen had gotten me from Potluck in the Park, which did the trick. Then a woman woke us both at 4 am, asking: "Do you know how to get to Broadway?"

"Get. The fuck. Out of my bedroom," is what I wanted to say, before finally deciding just to roll over. After all, I didn't want to get arrested for menacing. Having said that, a nice warm holding cell at the cop shop might have been preferable.

BREAKFAST OR CRACK?

We woke at 5:30 am, and tromped over to city hall's warm 24-hour restroom. I didn't really need the toilet; it was enjoyable enough just to feel the blast of hot air from the heater as I entered the front door. Then it was on to NW 4th and Glisan, to line up for breakfast at the Blanchet House.

Blanchet serves breakfast at 6:30 am, and we wanted to get in line early—but on the way down, at 4th and Everett, we passed another line. About 15 people were waiting, nice and patiently, for their dealer to dole out some crack.

"You cool?" the dealer asked us, as we walked past.

"Yes, thank you," I said.

I mean, what else do you say?

"You've probably burned up quite a few calories, sleeping out in the cold," Nolen told me, as I demolished Blanchet's breakfast: oatmeal, half a sausage, some orange juice, hot chocolate, and a bagel slathered in peanut butter. It was divine—there's simply not another word for it.

I have a nice job, a warm home, and I'm happy to say I've dined in some of the best restaurants in the world. But after a night on the streets, this breakfast was up there with the very best I've ever had.