AS AN ADULT, I can't bring myself to reread some of the books I loved best as a teenager. The Perks of Being a Wallflower is mortifying. Francesca Lia Block's Weetzie Bat series gives me a deep down, pit-of-the-stomach cringe. (I collected feathers and dyed my hair pink because of those books. ::shudder::)

The debut novel from Portland writer Lidia Yuknavitch—who wrote the great 2011 memoir The Chronology of Water—inspired similar feelings of discomfort. But it took me a while to parse whether Dora: A Headcase was making me cringe because its perspective is so nakedly, self-seriously adolescent, or because in writing from that perspective, Yuknavitch's prose strains for a youthfulness it never achieves. The answer is a little bit of both.

Dora is a fictionalized retelling of one of Sigmund Freud's case studies, about a girl—pseudonym Dora—who fielded the sexual advances made by her father's friend ("Mr. K"), while her father had an affair with the man's wife ("Mrs. K"). Yuknavitch re-pots Dora in contemporary Seattle, where she emerges a foul-mouthed, pill-popping 17-year-old who runs with a wild posse of teenaged art-fag miscreants. But the recontextualization only goes so far: Dora's psychiatrist is named Sigmund Freud, AKA "Siggy," and his dialogue is lifted straight from Freud's writings ("Your inability to admit your jealousy of your father's lover creates a crisis in consciousness."). There's even an appearance by Carl Jung as Freud's more magnetic counterpart.

Dora's narrative is crammed with references to pills and video art, cell phones and laptops—all the trappings of contemporary teenagerdom. But much of the action takes place in a sort of psychosexual liminal state, where every crack in the ceiling represents a vagina. In the novel's most loaded scene, Dora laces Siggy's tea with Viagra; when he checks himself into the hospital because his erection won't subside, she secretly films the ensuing surgery and watches the footage with rapt, sexual avidity: "When they stick the needle into his cock his face seizes up like his penis might blow fire. I suck in air and clench my hands between my legs..." and so on. Soon, shady media interests begin conspiring to buy footage of Siggy's surgery—and when Dora's love interest (a Native American girl who calls herself "Obsidian") is institutionalized, a weird caper ensues to bust her out. Amid all the symbolic penis-puncturing and high-wire plot hijinks, what's lost is character: Dora's friends are thinly sketched oddball clichés, and Dora's own narration strains credulity. ("By the way, I've taken Viagra, and though it's true if you are a girl it will drop your blood pressure to faint on the floor if you aren't paying attention, it can make your cum job do loop de loops. They don't like to tell women that. Typical.")

Where the novel breaks new ground is in its frank descriptions of Dora's sexuality—has a novel ever featured a teenaged girl explaining that she can almost get off on taking a giant piss? It also captures the electric, rattling-at-the-cages energy of being an unhappy kid: "I hate my twat. I hate my voice. I hate feeling anything about myself. I sprint my ass up to Nordstrom's." But this very real energy gets mired in Yuknavitch's convoluted, Freud-busting conceit.

The book's jacket calls Dora a "chick Fight Club." But the Portland author the novel really calls to mind is not Chuck Palahniuk—who wrote Dora's intro—but Tom Spanbauer. Dora shares a poetic, outsider-art intensity with Spanbauer's great In the City of Shy Hunters; both books are about sexual ambivalence, about creating your own family, about the transformative potential of art. (Also, being best friends with a giant black drag queen.) But Spanbauer's characters are grounded in a way that Yuknavitch's aren't, and his novel of transgressive outsiders finding themselves demonstrates a subtley and control that Yuknavitch's fiction debut never achieves.