Pineapple is honest to a fault, they said. So when their bosses at HBO in New York City in the late 1990s asked them what they wanted to do after their copy writing internship, they were honest: they wanted to move into video editing.
“They expected me to say, ‘I want to move up in this department here,’ because I’d done an internship with them, and moved up, got hired,” Pineapple said.
And even though Pineapple got what they wanted, and began video editing, they said they could not sustain the New York lifestyle on what was now freelance income.
But they felt out of place on the East Coast anyway. That carried memories of not fitting in at school, helping raise their little brother while their mom worked full-time and went to school full-time post-divorce, and a bout of mononucleosis that kept them from pursuing a music education degree.
They soon decided to come back home to the West Coast, having been born in Lake Stevens, Washington. They settled in Portland, where they have been since 2004.
Upon arrival, Pineapple spent a lot of time in Portland’s vast house show scene. Though currently disconnected from it, they hope to reconnect with the community that originally made Portland feel like home.
“I was doing promo and street team, where we actually walk around and hang posters with staples,” Pineapple said. “Most recently I was a hype girl for different DJs and producers.”
Somewhere between Lake Stevens, New York and Portland, Pineapple found their name at Burning Man.
At the festival, there were several people in their group with the same birth name as Pineapple’s, so the spiky fruit name was purely for utility at first. But it stuck, and Pineapple realized they preferred it over their birth name.
Pineapple said they are the same person around everyone. They don’t think it should be rare to find honest people, but they recognize that honesty can scare people.
“I feel for people that lie, because they have to remember what lies they’ve told and everything,” Pineapple said. “If you’re telling the truth, all you have to remember is what happened. You may forget something sometimes, but you’re not making anything up, or having ‘what I told this person, what I tell that person.’”
Like many others, Pineapple’s life changed drastically when the COVID-19 pandemic hit. They’ve been in and out of housing since 2020, and said they’ve faced housing discrimination for their disability. Pineapple walks with a cane.
“The reason that I’m homeless, and this person’s homeless, are probably totally different,” Pineapple said. “But a lot of people, they may be one disability check away from homelessness, or they may be one paycheck, getting hurt on the job, or getting fired, or whatever, from homelessness.
“I feel like it’s one of those things where, until you experience it, you don’t know what it’s like,” they added. “But I really wish that overall, people could just treat each other with kindness.”
You can find Pineapple selling papers at Ankeny Alley, as well as near the Fred Meyer off Northwest 20th Avenue & Everett Street. You can also support them by sending a tip via Venmo (@StreetRoots). Include their name and badge number (1333) in the memo.
This article appears in June 17, 2026.