S.P. Miskowski's new play Emerald City is, to quote the program, "inspired by real places and people but... a work of fiction." Miskowski, a 20-year Seattle resident (and editor of The Stranger in 1993), moved to Southern California a few years ago. West of Lenin describes the play as her "love letter/break-up note to Seattle." Just like real love letters and break-up notes, it can be awkward for someone who wasn't in the relationship to endure.

Our protagonist Scarlett (Jennifer Pratt) is a writer who moved away from Seattle and is forced to return for a freelance assignment that her agent assures her is a career-saver. Having lost a job, house, and lover in the city, the prospect of returning has her on edge, snapping at or ignoring her girlfriend while calling and pleading with her agent to get her out of the deal.

The girlfriend, Lillian (Megan Ahiers), is an airhead who dotes on Scarlett but obviously feels mistreated. Their first interaction goes like this:

Scarlett: Listen to this.

Lillian: Dinner soon.

Scarlett: I know. Listen.

Lillian: Is this going to make me sad?

Scarlett: You should read the news.

Lillian: I don't like it. It makes me sad.

Scarlett: Okay. I'll tell this one like a fairy tale, how's that?

Refreshingly, this all-woman play passes the "Bechdel test" (which requires that a story have at least two named women discuss something besides a man), but characters like Scarlett and Lillian don't exactly make me feel like I'm supporting awesome feminist theater. Scarlett flies off and stays with her college roommate Tina (Morgan Rowe), a Seattle version of Lillian: a hippie airhead without a shred of self-awareness. In one conversation, Tina talks to another character about moving to Seattle from Tucson. She says with utmost drama that her pottery teacher in Seattle told her she should "'look inside her heart.' You know, that's code here," she continues. "It means: Your pottery sucks. In Tucson we just say, 'Your pottery sucks.' In fact, a lot of people in Tucson told me that."

There are only five characters in Emerald City; two of them are dumb as rocks, which is less than entertaining. While those two are annoying, watching Scarlett talk down to them is even worse; she's so bitter we have trouble empathizing. "I like to start the morning by getting in touch with my sense of wonderment," Tina tells her. "You mean wonder?" Scarlett asks. "Wonderment," Tina answers. "Wonder doesn't express how truly amazing life is." Who wouldn't want to laugh in her face? But watching Scarlett do just that is uncomfortable.

Scarlett is working on an article for the Los Angeles Times about Dot (Gretchen Douma), a woman who won't sell her family's old Ballard Craftsman to developers. (The set is based on the Ballard home of Edith Macefield, an elderly woman who made headlines in 2006 by refusing a $1 million offer from developers who then built a huge gray building surrounding her home on three sides.) Scarlett's interviews with Dot are also uncomfortable—she forgets to turn on the tape recorder, she falls asleep, she can be oddly accusatory and combative. Dot is a wacky old-lady caricature who might have wisdom to offer if only Scarlett were capable of listening.

Between endless monologues about Seattle history from Dot and Tina and an improbable subplot in which Lillian flies to Seattle without telling Scarlett—she drinks tons of coffee, goes on every walking tour, and gets a tattoo of Chief Sealth's daughter, and generally falls in love with the city—Emerald City feels too long by half.

Pratt, Ahiers, Rowe, Douma, and Shawnmarie Stanton, who plays Scarlett's bitchy agent, are all talented actors and they're not exactly failing here. Ahiers cracks up the audience by pulling faces and Pratt renders the exasperated, anxious Scarlett with a tight-faced frustration that feels real. But they're working with material that seems very personal to the playwright, and a script that feels unfinished and under-edited. This mash note/breakup letter needed a lot more polishing on its trip between Miskowski's raw experience and the stage.