I stood in a drafty living room covered in beer cans, overflowing ashtrays, and suspicious stains. The most striking aspect was one wall: a slurred mess of paint and drawings created by a mind obviously working from a different dimension—a cracked-out dimension.

But at the moment, this was my best bet; a party house wedged between a noisy intersection and a McDonald's. I, like so many other frustrated temporary homeless, was on a search to rent a room in Portland.

Who knew it could be this tough?

London Calling

Last summer, I moved back to Portland from London, where I lived for half a year. By the time I arrived back in Portland, I considered myself a "flat" search veteran, because nowhere else, except for perhaps the Gaza Strip, do they pack people in more tightly. Getting a room in London was also tricky because once a room was posted on the internet, it was usually snatched up by the next day.

It took about two weeks of hard searching to find a room. During my hunt, I ended up in dodgy corners of East London, and once found myself trudging across a field near a highway, cursing myself for thinking Greenwich looked "close enough" to central London on the map.

Since most Londoners are from out of town, they're willing to put up with crappy living conditions. I thought I'd seen the worst when I met a jumpy Asian apartment owner in a stinking alley in Camden Town, a hip neighborhood in North London. He opened a door wedged between two shops and led me up to the flat. It seemed like a bomb filled with spoiled food and dishes had exploded in the kitchen. Inexplicably forgotten among the mess sat a whole raw chicken. Six Brazilian men were sleeping in bunk beds in what at one time might have been the parlor. Though a room overflowing with handsome Brazilians was tempting, I decided the chicken was just too much, and eventually found a different flat.

So while finding a room in London was difficult—it's a snap compared to Portland.

Just Four Walls and a Roof

Rooms in London were snatched up so quickly because London flatmates want someone decent (i.e., not a serial killer) and they want the person now—as in "can you move in tonight?" In comparison, Portlanders are a bunch of fussy aunts who want to know if your particular style and personality will fit perfectly with their carefully constructed social Feng Shui.

To do this, they write lengthy ads describing themselves and their ideal roommate in detail. Portlanders ask you to fill out a questionnaire rivaling those for prospective Secret Service agents. One ad asked a total of 39 questions, including: Pet peeves? Single or not? Sleepovers? Light sleeper? Favorite holiday? Do you have much stuff? Can you talk superheroes? Are you willing to accept the fact you will probably step on a Lego or toy car at some point and see some small child using the potty with the door open? The ad also included this cheery addition: "feel free to add more [information]... no BS and no faking it... this is meant to be enjoyable."

Well, to answer your questions, I never fake it and I know this is meant to be enjoyable, but I am indeed a light sleeper and would not appreciate a sleepover with you. And my pet peeve is people who want you to answer almost 40 questions before even talking with you in person. And I'm not babysitting your goddamn kid so it doesn't matter if I can "talk superheroes."

Another ad I found on craigslist was priceless. A "dyke Wiccan permaculturalist" was looking for another dyke Wiccan permaculturalist to share her farmhouse. One of the ad's many house rules was, "If it's yellow, let it mellow." There would also be Wiccan rituals performed on the grounds. And BDS&M.

I think there are probably two other dyke Wiccan permaculturalists in Portland, and they're already dating.

I decided to give Portland's temporarily homeless a chance to vent about the difficulty of finding a room to rent, and placed my own ad on craigslist. This is what Larry Graham had to say: "Some people will only rent out to vegans... others, you have to be a liberal or conservative, or you have to be a Christian and you can't drink. I mean, all I'm trying to do is look for a room to rent. I'm not looking for new parents!"

One of the most frustrating signs of pickiness is that craigslist is a cyberspace black hole—sucking in your replies and yielding no returns.

T'chaka Sikelianos, a 3-D animator for a media company, has only been looking for a few weeks, but is already frustrated.

"Although the market seems to be flooded with room rentals," he said, "it's like getting blood from a stone. I think I've sent out 15 inquiries and not one, not one, person has gotten back to me."

"I've been on craigslist for about three months now and have emailed probably 100 people. I've gotten one reply," wrote Usana Tron, a 29-year-old bricklayer and musician. "I realize it's a tough market, but this is ridiculous."

If you manage to get a response, after sending out your required 100 or so emails, it's time to turn on the charm.

"I went through a search that lasted a couple months," said Stephen Judkins. "When I did find a place I liked, it felt like I was in an audition to see who'll be the coolest roommate."

That's hitting the nail on the head—to get a place, it's no longer important to be just a cool person... but the coolest goddamn hipster in Portland!

Which brings me back to the gritty party house next to McDonald's. Having finally received a response, I knew it was time to be so dazzlingly hip I would outshine everyone else grappling for this cheap room. Yes, beer cans covered every surface, the place stank like old cigarettes, and was painted by tweakers—but hey, I'd seen worse. And I'd been looking for two months.

Meeting the housemates felt a bit like a networking cocktail party, except everybody was in black and had at least one piercing. Three of the five housemates were there, and we were all getting along fine, laughing, name-dropping. That is, until the last two housemates showed up. One of them, let's call her Blair, would win the prize for über-hipster. She had a black mullet and a dozen tattoos. She gave me one snide look and said I looked too "straightedge," even though I was wearing jeans and a corduroy jacket, not a periwinkle sweater set.

"We do hard drugs here on a regular basis—like heroin," she said, as if she was accusing me of something.

I visualized junkies stealing my boots, needles in the couch, and cop raids in the middle of the night. Could I jump from a second-story window onto the roof of McDonald's? Maybe I was too straightedge.

It was weeks before I had my next offer. A lesbian, a stripper, and her four-year-old daughter had a room open in their house. Was I kid-and-kink friendly? You bet. Was I a feminist? Definitely.

"Do you have an STD?" was the first question Sarah asked when I showed up at her door. "It's my experience that housemates usually end up sleeping with each other." She laughed manically and offered me a bowl of soup.

Yes, the house was on a freeway onramp, but the soup and homey atmosphere were perfect and we all got along. The kid was cute and well behaved. They asked me to move in.

Victorious, I visualized living there for years. Hey, I wouldn't even mind watching the kid once in a while. Maybe I'd teach her rummy.

One evening, a few weeks after I moved in, Sarah off-handedly said she should really get around to calling the owner of the house to ask if I could move in.

"Ask?" I'd already moved in.

"He likes to be asked."

She made the call. He said no, he wanted a family in that house and not another single person. He wouldn't even meet me. Now, technically, this was illegal—an owner can't discriminate against someone for not having yet procreated—but I didn't want to throw a fit and have everyone kicked out. Cringing, I once again joined the losers trawling craigslist.

I made more calls, met more assholes, and saw a room where the only entrance was through the bathroom.

Finally (miracle of miracles), I answered the ad of an actual reasonable guy named Mike. This was his list of demands: He wanted someone who would pay the rent and wouldn't cause drama.

I moved in the next day.

Thank you, Mike, for providing two requirements I could finally handle. I've learned my lesson, and I will never, ever leave.