Madeline Key as "Now" Jane in "The Oregon Trail" by Flying V. (Ryan Maxwell Photography)

Bekah Brunstetter is a terrific catch for Bethesda’s small Flying V Theatre. The Los Angeles-based writer enjoys steady work on a cable series (“Switched at Birth”) and has a premiere slated this season at one of California’s top companies, South Coast Repertory. Yet Flying V has landed the premiere of Brunstetter’s “The Oregon Trail” as part of D.C.’s sweeping Women’s Voices Theatre Festival , and it’s putting on an appropriately playful, thoughtful show.

The play is a breezy fantasy about a sad girl named Jane who loses herself in the quaint video game “The Oregon Trail.” Jane’s a slouchy, cranky schoolgirl when we meet her (it’s the 1990s — you can tell by the floppy disk she slips into the computer lab’s massive desktop). Actually, Brunstetter calls this character “Now Jane,” because inside the game there’s “Then Jane,” a 13-year-old being uprooted from 1848 Missouri as her family makes the 2,000-mile trek west to Oregon.

Brunstetter draws you in with puckish humor as the touchingly written Now Jane, played with carefree patter and a careworn soul by Madeline Key, withdraws from life and sinks into the game. “What’s your choice?” the computer (amusingly voiced by Zachary Fernebok) asks Jane. A crisp sequence catapults Now Jane into adulthood via game-voiced “choices” that land her on her sister’s couch, directionless and gloomy in her 20s.

Meanwhile, in the 1800s, Then Jane (Kelsey Meiklejohn, plucky and serious) slogs across the country with her taciturn dad and older sister. They tote a load of grief in their covered wagon: Then Jane’s mother has died. The play toggles smoothly between centuries as the Janes’ shared subject emerges, and Brunstetter establishes distinct linguistic patterns yet lets her imagination run free as 1990s pop hits somehow get sung in the 19th century.

This is frisky writing, and director Amber Jackson’s modest production is at ease with tones that shift from punch-line funny to cripplingly depressing The acting is laid back — too understated at times, although Key is always right in tune and unfailingly likable — and Kathryn Kawecki’s efficient set is basically a school interior with a prairie mural that makes it easy to swing between periods. In the school, for example, Key’s Now Jane shares an aching, delicate encounter with her older-boy crush Billy (Will Hayes). On the frontier, Then Jane, her father (Ryan Tumulty) and her sister (Julia Klavans, the sister in both eras) endure an action-packed and smartly executed scene trying to cross a swollen river.

It’s a tricky play, to be sure, and you can see the hazards — although the script’s strong upside landed it on “The List” put out for the first time last year by the Kilroys, the L.A. group dedicated, like the D.C. festival, to addressing the ingrained gender imbalance in American theater. (Brunstetter is a founding member of the Kilroys.) The life-as-game gambit could skew too cute, although it certainly doesn’t here — and yes, Now Jane is bright but an inert mess. But that prickly personality and its discontents ring awfully true, and Brunstetter uses the game frame to her wry advantage, switching it off at will. Even some over-explaining in the final steps doesn’t erase the pleasure of this quest.

(Footnote: “Oregon Trail” and Kathleen Akerley’s “Night Falls on the Blue Planet” at Theatre Alliance opened this past weekend, the third and fourth of the four dozen or so shows in the Women’s Voice’s Theatre Festival’s two months of premieres by female playwrights. The festival’s big launch event is Tuesday night.)

“The Oregon Trail,” by Bekah Brunstetter. Part of the Women’s Voices Theater Festival. Directed by Amber Jackson. Costume designer, Kathryn Kawecki; sound design, Neil McFadden; lights, Kristin A. Thompson. About 100 minutes. Through Sept. 20 at the Writer’s Center, 4508 Walsh St., Bethesda. Tickets $15. Visit www.flyingvtheatre.
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