Long Winters songs can instill the listener with strong feelings of longing—what frontman John Roderick calls the "temperature of regret." He gracefully evokes the feelings of slowly losing something once held intimately close. Of moments where, as he sings on "The Commander Thinks Aloud" (off the excellent new Ultimatum EP), "the crew compartment's breaking up"—a metaphor for watching love slowly implode with great intensity. Or on the title track, when our narrator exclaims, "My arms miss you, my hands miss you... I hope I can keep seeing you/As long as you don't say you're/falling in love."

Since it's an annual tradition at The Stranger to end the year with regrets, I took a subject-specific trip with Roderick—who not only writes soaring pop songs of love and lament, but who is also something of a local historian. His family has lived in Seattle since the 1870s; his relatives were city fathers who worked as lawyers and justices of the peace, and who helped found the first Seattle Public Library. Their histories are inextricable from Seattle's in the same way that Roderick's lyrics are inextricable from the human condition of trying—and failing and trying again—to connect to something bigger.

On a recent rainy afternoon, Roderick and I toured Seattle as he mapped an interlocking collection of regrets, from relatives with "great-great" in their relations to a flophouse where roaches got the best of our hero. My one regret about the experience: that I don't have space to relay how Roderick walked across Europe—from Amsterdam to Istanbul—when he turned 30. His one regret from that experience: "I had really shitty boots at the time and I didn't have the brains to get rid of them."

Place: Pier 48

Date: 1886

Regrettable Incident: Great-great-granduncle Junius Rochester attempts to run the Chinese out of town

In the wee hours of February 7, Junius Rochester, a lawyer, led a violent anti-Chinese mob here to try and scare immigrants into hopping ship to San Francisco. "This torch-carrying mob woke people up in the middle of the night and said, 'Get what you can carry because you're getting on a boat,'" Roderick says as we stare out at a near-empty pier. "And then there was another mob of anti-vigilantes who came down here and they had it out. People were running up to the courthouse and filing injunctions on behalf of the Chinese and opposed to the Chinese. They were standing on soapboxes and getting in shoving matches. Shots were fired. My great-great-granduncle was a first-class bad guy in this story," he adds.

Place: Japantown

Date: Early 1942

Regrettable Incident: Straw-hatted old lady disapproves of Japanese friends

Roderick's father, David Roderick, went to Broadway High School, which in the early 1940s had a fairly substantial Japanese population. When the Japanese bombed Pearl Harbor in 1941, some of David's closest friends were suddenly considered "enemy combatants." Roderick's father remembers walking with Japanese friends when an old lady stopped him on the street because he was "consorting with the enemy." "America oscillates between two poles of 'Hey it's a prosperous time, live and let live' and 'There's a perceived threat that makes us all scared, so we'll scapegoat some people,'" says Roderick. "My dad has mixed feelings about that whole time... he joined the navy and was sent to the South Pacific to fight the Japanese."

Place: Capitol Hill, across from Volunteer Park

Date: 1972

Regrettable Incident: A conflicted sense of home

In the '70s, "hippies and druggies" were overtaking the elegance of Capitol Hill, but Roderick's grandmother, Mary Louise Roderick, remained in her childhood home with her grand piano and worn Oriental carpets. Her sisters believed the neighborhood was turning "bad," and pressured her into selling her house. Before the ink dried, though, Mary Louise died. "She went from healthy and vibrant to dead in two weeks," says Roderick. "All that remains of the house my great-great-grandfather built on that site in 1902 is the fire hydrant out front." The rest was torn down in the '70s to make room for "the monolithic brick Gulag that stands there now."

Place: Capitol Hill, Harvard Street

Date: 1993

Regrettable Incident: A pistol and awork-release roommate

Over three years of what Roderick calls "increasing drug use in a real shithole apartment," the Long Winters frontman remembers failed attempts at turning his passion for history into relevant songwriting. "I didn't own a guitar, but I filled 20 spiral-bound notebooks with what I thought were really smart indictments of Western civilization." His roommate situation was loveless, to say the least. "Every time I came home my roommate would be there with like six other guys who I'd never seen before, and they'd be like, 'What the fuck do you want?' And I'd be like, 'This is my apartment, I live here.' And they'd ask my roommate if I was 'cool.' There was a constant feeling of unwelcomeness."

That vibe continued when one housemate borrowed the gun Roderick kept in his closet. "My roommate was smoking crack one weekend and someone insulted him on Broadway—so he took my pistol and found the guy and made him kneel in front of him. The cops came. He was on work release and was supposed to be in the jail when he wasn't at work."

Place: Capitol Hill, near the Wing Dome

Date: 1996

Regrettable Incident: A Rat and his God

As we pull up to the narrow wedge of the Belvedere apartments, Roderick takes a puff on another cigarette and says, "This is a truly disappointing episode of my life." A year of trying to write songs that were more "emotionally true" at this flatiron ended after Roderick's cohabitants included too many rats and cockroaches. He complained to his Hindu apartment manager, who responded, "Why do you complain to me? I did not make the rat. I did not make the roach. If you have a problem you should talk to God." Roderick adds, "He was dead serious; he meant it philosophically. When I moved out a few months later, I took all the light bulbs with me. God stayed out of it."

Place: Washington Mutual

Date: A couple years ago

Regrettable Incident: Conversational machines

Listen to Ultimatum's "Everything Is Talking" and it might sound like the song's about technology pulling people apart. But Roderick admits that his impetus in writing it was much more specific. As I drop him back at his Central District abode at the end of the day, he explains. "That song is basically about the cash machines at Washington Mutual. I went to the ATM and the machine addressed me in what I considered to be a language too familiar. It was like, 'Hey, what language should we go with, English or Spanish?' 'Cool, what kind of cash would you like, yo.' I was so offended that someone had programmed this cash machine to speak to me so familiarly. I wanted it to call me 'sir.' It's symptomatic of our whole culture moving toward a place where the idea of what's classy is just the trashiest trash. I'm waiting for the bank to put semicolon smiley faces at the end of my statements. The day my bank tells me to LOL I'll withdraw all my money from the bank and just keep it in a pillowcase."