If you were a child in the ’90s who wore a bonnet for fun, there may be no phrase in the English language more mordantly comforting than: “You have died of dysentery.”

Between the Laura Ingalls Wilder books, pioneer American Girl dolls with tragic backstories, and the alluded to computer game (released on floppy disks for Microsoft DOS in 1992), I was one of those strange eight-year-olds. So when I found out that Portland Center Stage was producing Bekah Brunstetter’s The Oregon Trail, a play about a grown-up ’90s kid rediscovering the joys of traveling the trail, I was sold.

Until I actually saw it.

Brunstetter’s play centers on Jane (Sarah Baskin), an unemployed 25-year-old crashing on her sister’s couch, who plays The Oregon Trail in between avoiding the job search, drinking heavily, and sleeping with inappropriate men. She’s a mess, basically, and probably clinically depressed, although the play kind of dances around this fact.

That’s too bad, because one of Brunstetter’s strengths is her choice to embed sad adult themes within the confines of a beloved children’s computer game. And for a play that’s ostensibly about depression and many forms of survival glimpsed through a deceptively whimsical lens, The Oregon Trail is disappointingly lightweight. The play’s sentimental, tacked-on ending passes off Jane’s depression not as depression at all, but as superficial, early-twenties existential ennui. But there’s a difference between feeling sad and not being able to get out of bed or hold down a job, and it’s annoying to see debilitating depression depicted as something that a little bootstraps ingenuity can solve. I was nearly as irritated by Brunstetter’s dialogue, which can be obnoxiously cute: At times, it sounds more like the idea of how millennials talk than how millennials actually talk.

If you loved The Oregon Trail, there’s probably enough here to keep you entertained. The soothing MS-DOS interface the play opens with (Leif Norby’s wonderfully charming voice-over listing Jane’s options as the game itself), Emily Yetter as Jane’s more well-adjusted sister, and the comfortingly low-tech logo of the MECC educational computer software company written large above the stage. There are some creatively employed songs from the late ’90s and early ’00s (although I can’t say I was psyched to hear Bush’s “Glycerine” almost in its entirety).

But it’s hard to argue that it wouldn’t be more fun to just play The Oregon Trail, which you can now do online, for free—a fact written into the script of this Oregon Trail, just in case you didn’t already know.

(I did.)