Portland Center Stage's attempt to appeal to millennials isn't exactly sly. The plot of the new comedy, The Oregon Trail, relies on nostalgic association with the floppy-disc computer game of the same name that was a staple of middle-school computer labs. Not only does The Oregon Trail feature an HBO-style lack of censorship (including a bare-vagina, bare-butt doggy style sex scene), but there's also a photo booth outside the theater that suggests the play's title for your hashtag.

Given the title of local playwright Bekah Brunstetter's work, it could be easily mistaken for a period drama. And in the loosest sense possible, half of it is. Oscillating between 1848 and 2009, it's a tale of two Janes: one a hopelessly depressed modern-day Oregonian (Sarah Baskin) and Jane's great-great grandmother (Alex Leigh Ramirez), forced to follow the grueling Oregon Trail.

Propelled through time by a narrator (Leif Norby), Now Jane is a broke college grad kicked out of her parents' house, unable to find a job and paralyzed with fear at even having to choose one. In a depressive stupor on the couch of her well-adjusted sister (Emily Yetter), Now Jane sits at her laptop and plays The Oregon Trail, craving distraction but instead gaining insights into her family's history of depression.

But it's never exactly called that. Now Jane is seen on the couch at all hours, promising to clean her space and never doing it, lying to her sister about spending the day searching for jobs, chugging whiskey from a bottle, sleeping all day, watching loud TV all night, neglecting personal hygiene, and talking to herself: "Get up. Get up right now. Now."

When Now Jane meets up for an ill-advised drink with her middle-school crush Billy (Chris Murray) and mentions she's been "sort of depressed," he says, "Like, clinically?" She denies it, panicked and embarrassed.

Other than this brief mention, Now Jane's depression is only referred to as "sadness," "melancholy" or an unnameable "weight" on her chest. Never is there mention of therapy or medication, despite several casual mentions of suicide.

The play's fundamental concern with sadness makes its two central characters less dimensional. Then Jane's rebellious negativity can be easily explained by the deaths of those she's close to; Now Jane's shoulder-slumped helplessness is the defining characteristic of her life. This feeling of flatness was in no way the fault of the actors, though: Baskin brings remarkable complexity to Now Jane's character.

The Oregon Trail's premise is fresh, and some parts are quite funny, but it misses the greatest opportunity it carves out for itself: a chance to really talk about depression. The play's "somebody else had it worse" philosophy does not actually help depressed people—and neither does making light of hopelessness and poor life decisions, which The Oregon Trail does constantly. The play leaves its audience with the vague, unhelpful advice to just "continue on the trail."

SEE IT: The Oregon Trail plays at Portland Center Stage, 128 NW 11th Ave., pcs.org. 7:30 pm Tuesday-Sunday, 2 pm Saturday-Sunday, noon Thursday, through Nov. 20. No 7:30 show Sunday, Nov. 13. $25-$70.