Starring in Fault Line Theatre’s production of Bekah Brunsetter’s new play The Oregon Trail, the wonderful Liba Vaynberg brings the show’s humor to life with her portrayal of “now Jane,” a '90s middle schooler with an overbearing older sister (Laura Ramadei), a distinct lack of social grace, and an unrequited crush on Billy (Juan Arturo), her neighbor and bus buddy. Stuck in her school’s computer lab, waiting for her mom to come pick her up, Jane passes the time by playing the titular computer game, while its narrator makes increasingly personal comments (would you like to begin your journey in March, April, or May, “when the sun starts to smolder and your bangs stick to your face no matter what you do, and you are disgusting”).

Guided by the omniscient narrator of the game, the play takes us through Jane’s mediocre college experience, lackluster first job, and subsequent unemployment, a rut that lands her on her successful older sister’s couch. Besieged by a sadness she cannot define, one that’s been inside her since middle school, Jane rediscovers the Oregon Trail, and turns to it escape the hopelessness of her couch-sequestered life.

As Jane plays, both in middle school and adulthood, the play introduces “then Jane” (Emily Louise Perkins), who is reluctantly joining her family on the real Oregon Trail centuries ago. Dragged away from her beloved home by her father and way-too-perfect sister (also played by Laura Ramadei) after the death of her mother, Jane finds herself struggling to survive on a perilous journey where every choice is life-or-death (and you don’t get to press spacebar for a do-over).

Liba Vaynberg sat down with us to share her experiences at the center of a heartfelt exploration of coming-of-age and depression, doused in nostalgia and biting wit. Her experience with the show began with this production, joining cast members who had followed the play through incarnations in workshops and readings. She said of that introduction to the play, “It’s great to jump into the play fresh, but it’s also great to be surrounded by people who have been working in it for a long time, and learn about it from them.” Part of what made it such a wonderful experience was her work with director Geordie Broadwater, whose approach Vaynberg said helped her bring out the nuances in Jane’s character, especially her struggle with a lifelong, inexplicable but all-too-tangible sadness that follows her from adolescence to adulthood. “Bekah’s description of Jane’s sadness is something I think everyone has felt, at some point in their lives,” Vaynberg said. Her character gets her fair share of that sadness, as both she and then-Jane struggle with finding purpose in their lives, and meaning to drive their actions.

Part of the play’s success lies in its structure, a duality that’s a unique find for the stage. As Vaynberg said, “It’s a common structure in film, where you shoot it separately, and put everything together in front of a computer. In a play, it has to be right there in front of you, and you have to find a way to put the two worlds together on the stage.” The Oregon Trail puts its two stories side by side onstage, moving seamlessly between them without letting one distract from the other. Instead, the experiences that forge Jane in each narrative create rich connections between the two storylines.

Within that unique structure, Vaynberg found a whole new depth to her character and the story through the parallel tale of Jane’s ancestor, then-Jane, as her performance evolved to work as a successful counterpart to Emily Louise Perkins. Despite their vastly different situations, both Janes grapple with similar questions, and the parallels in their internal challenges and familial dynamics build common ground between them. As a result, Vaynberg described her performance as both building from similarity and reaching for differences between the two Janes. “Emily and I have a lot in common, and we’ve become close friends,” Vaynberg said. “But we’re not exactly the same. The Janes’ stories aren’t exactly the same, that would be redundant. It’s informed my performance in that way, by finding ways to be her complement. Like looking in a mirror. It’s similar, but it’s the reverse.” The two certainly find this balance well, their performances connecting the two characters while finding fresh nuances within each story to differentiate them.

Unlike the character she plays, Vaynberg didn’t play Oregon Trail – until she was cast, that is. “It was so addictive,” she said. “I think you can definitely zip through it faster as an adult. You can actually get to the end of the game!”  The computer game is part of a larger nostalgia that characterizes Jane’s middle school experience within the play, which Vaynberg says captures the spirit of that point in time: “With her outfit, Jane’s sister could be in Clueless!” Though certain bits in the show certainly bring up nostalgia for audience members who lived through them (as Vaynberg pointed out, “Things like the floppy disc make people in the audience who experienced that laugh, and everyone else laughs along with them”), but Brunsetter’s writing skillfully encapsulates adolescent Jane’s era, creating a portrait of young Jane’s life that transcends nostalgia to resonate with audiences of all ages.

While Jane’s relationship with her ancestor gives the play its thematic weight, it is Jane’s relationship with her perfect older sister that fuels her character arc. Even though a romantic subplot pops up as part of Jane’s journey, Vaynberg describes it as decisively secondary to Jane’s relationship with her sister. As she says, “Sisters never leave.” This fact underlies the play as a source of support, even if at times reluctant, for Jane.  As the oldest sister in her family, Vaynberg might relate most to Jane’s older sister, but rose to the challenge of portraying the needier younger sister beautifully, portraying the struggle that comes with simultaneous love, frustration, a need for guidance, and a desire to please corrupted by an inability to follow through. Put simply, “There’s a reason, when she hits rock bottom, that Jane ends up at her sister’s house.”

Those relationships at the center of Jane’s life bring the play to new heights, and Vaynberg’s performance captures the meaningful connections throughout Jane’s life beautifully, making The Oregon Trail a must-see play for anyone who’s struggled with finding their purpose, or just really misses their floppy disk of computer games.