The best novels about teenage sentimentality

As a debut novelist, I face this nagging sense of obligation to prove myself to the world as a Serious Writer And Thinker, and thus I was initially a bit sheepish about recommending a young adult title here.

It’s in the service of the very unabashed earnestness this list commemorates that I’m forcing myself to get over it and say the following: there are few elegies to the wistfulness of adolescence more poignant or haunting than The Perks of Being A Wallflower.

I read it for the first time as a seventh grader in 2006 and probably six more times in as many years thereafter, each time bewitched by its narrator (a sad, quiet ninth grader named Charlie), its conceit (a series of letters from Charlie to a nameless stranger), and of course its story.

Following Charlie through his first year of high school, we intimately witness the shattering of his innocence—the novel is unsparing in its depictions of sex, drug use, and many genres of violence—and see that there is beauty to be found in the mosaic made from its shards.

“Sentimental” is maybe the last word you’d use to describe Ellis’ fiction, but Less Than Zero is an elegant proof that form needn’t follow function.

For all the sparseness of its language and pitilessness of its characters, there is a profound empathy for its narrator Clay, a pensive college freshman who’s returned home to California for Christmas break. Clay expends no outward moral judgment on the depravity of those who populate his very Gothic Los Angeles, but we come to intuitively understand his reticence as less a disposition than a defense.

It is precisely in how he understates his pain that we feel just how total it is.

This is another novel written expressly for teenagers, and all the better for it.

Inflected by the author’s own autobiographical experiences—like Craig, the novel’s narrator, Vizzini spent a week in a psychiatric hospital as a teenager—It’s Kind of a Funny Story was the first work of fiction I’d read that articulated the adolescent experience through the language of mental health. It was here that I learned “depression” isn’t an abstracted emotion but the very real neurochemical imbalance that impels Craig to call the suicide hotline after abandoning his SSRIs.

There’s an uncanny familiarity to the circumstances of Craig’s breakdown—namely in how he struggles to remain above water at a famously rigorous college preparatory high school—and a fundamental earnestness to his story’s confessions that gilds even its grimmest moments with a fifteen-year-old's sense of impressionable wonder.

I’d normally abstain from the pompous sin of quoting one’s own fiction, but I’m doing it here only to contextualize this recommendation.

“Adolescence is an exercise in coveting what exists just beyond our grasp,” my book’s narrator tells us in his preamble to his telling of Foster’s story. “It is this inaccessibility that sustains its magic.” To be fifteen is to be a voyeur looking wistfully in on the poignancy of others’ lives: this is the idea I tried to operationalize through the narrator’s project, with full knowledge that I’d never do it as lyrically as The Virgin Suicides. 

Nominally, the main characters of Eugenides’ debut are the five titular Lisbon sisters, who successively take their own lives, but we encounter them chiefly as figments of a collective imagination: in the captivated minds of a faceless group of teenage boys who witness the tragedies from afar.

As a sort of Greek chorus, these boys together reconstruct the Lisbons’ story, but it’s less the story of these girls’ deaths than of the boys’ own fascination, which refracts truth into mythology. 

I tried to avoid boarding school novels while writing my book, fearing the sort of subliminal influence that would subject my own book to accusations of being derivative, but about a month ago I returned to A Separate Peace for the first time since maybe ninth grade.

I was struck by a lot that I’d missed then—namely the undercurrent of bristling homoerotic tension between Gene and Finny—but more pointedly, I felt a new sense of solidarity with Gene, who narrates the events of one summer at boarding school from the comparatively distant vantage of early adulthood. I recall Gene the narrator seeming impossibly old when I read the book in high school, but at thirty I saw a colleague: not only in the facts of his present but in his relationship with the past.

Those of us who came of age in the enclosed ecosystems of boarding school all have stories like Gene’s about Finny: stories of peers who seemed somehow radiantly superhuman; of happenings and events that assumed the weight of tragedy in our minds.