Sometimes, against my better judgment, I’ll type some rankling concern into Google. “Sleeping hip pain?” “Sad always on Wednesday?” “Laptop way too hot?” Most of the time, autofill assures me that a chorus of other users have shared this predicament; it is neither unfixable nor unique. But for the occasional search, even an algorithmic process as vast and powerful as autofill can’t predict how my question should resolve itself. Worse than a WebMD cancer diagnosis or the graphic advice in an obscure Reddit thread is an endless list of results that don’t quite see what I’m getting at. In “Ask Me Again,” her debut novel, Clare Sestanovich dwells in that ambiguity, seeking community in shared questions that may not have answers.

“Ask Me Again” opens with a morbid meet-cute: Eva, a middle-class Brooklyn high school student, encounters Jamie, a wealthy Manhattan private schoolboy, at a hospital where she is visiting her grandmother and he his alcoholic brother (illness and death trample over class lines). Eva’s grandmother, Adele, has just attempted suicide. Though Adele has been devoutly Catholic her whole life, she is now widowed, incontinent and alone: God has betrayed her. The doctors try to explain away her misery with brain tangles or plaque, but Adele insists that “she was not confused – she was furious.”

The void awaiting Adele at the end of her life becomes the engine of Eva and Jamie’s friendship and their search to determine what their lives are really all about. In the nascent days of friendship, which can feel like falling in love, Eva and Jamie develop a fascination with trees: “Crown shyness,” Jamie explains to Eva, is when trees “grow and grow and then, just when they’re about to converge, they stop.” Eva and Jamie keep in touch over the ensuing years – sometimes intensely, sometimes more distantly – their friendship occasionally bending toward romance (“We’ve both at least considered the possibility of seeing each other naked,” Jamie observes to Eva when they’re seniors in high school) but never quite crossing over. Their friendship inclines more toward existential conversation than physical desire as they join different institutions that sometimes pass for community: Eva attends a prestigious university and falls in love with an aspiring politician, while Jamie joins an Occupy Wall Street-like encampment before devoting himself to a church. (Sestanovich frequently writes about modern phenomena like Occupy without ever naming them, a common technique among contemporary novelists.)

How do you find meaning in modern life?, Sestanovich asks. Can love materialize from the e-commerce interfaces of dating apps? Do virtual sermons still get the message across? Her chapters are titled with similar queries that might sound rhetorical but are in fact quite profound: “What’s it worth?” “What do you mean?” “Is that all?” Sestanovich, an editor at the Drift whose fiction has been published in the New Yorker, is also the author of “Objects of Desire” (2021), a stunning collection of short stories that features mostly young, female protagonists grappling with what it is they actually want. (In the title story, one listless woman’s ex-boyfriend has just been elected to Congress, and, like Eva, she is envious, if skeptical, of the politician’s capacity to hold a clearly outlined ideology.) In “Ask Me Again,” Sestanovich shakes the Magic 8 Ball over and over, probing for answers but finding more questions.

Preachers, parents, professors, newspaper advice columnists – “Ask Me Again” isn’t short on people who seem to have answers. Eva studies philosophy and, after graduating, finds a job at a newspaper as a researcher and then as an editor for the paper’s Wellness section, where the gospel is dispersed in articles about seven- and nine-minute workouts. Jamie, with more financial latitude, is wholly committed to embodying his principles: He drops out of college and disowns his 1-percenter parents, starts working at a church and discovers God. Eva befriends an AOC-inspired political candidate who is always reckoning with how to execute her vision without compromising it, a predicament that is almost enviable to Eva: How can she defend her principles when she’s not even sure what they are?

The internet offers fleeting moments of connection, but it also distorts the institutions where people have traditionally turned for solace, like one of those former churches subdivided into condominiums that proliferate on Zillow, with stained-glass windows above laminate flooring. When Eva’s grandmother is hospitalized, her parents consider calling a priest whose “rites could be administered by Skype”; Eva logs on to Jamie’s church for virtual services before turning to her mindfulness app instead. But if the internet renders everything, even scripture, in the same anemic Helvetica typeface, there’s still holiness to be found in the quotidian: “Faith is as mundane as it is profound,” Jamie’s pastor preaches. Sestanovich is critical of long-standing institutions and snake oil salesmen alike, but she’s never cynical about faith and the pursuit of it. Even in the smoggy urban landscapes of New York and Washington, Eva witnesses miracles.

If Sestanovich’s thematic ambitions are broad – the meaning of life, the coherence of identity, the possibility of principles – her language is cuttingly precise. Latin, Eva’s high school teacher observes, is full of “complex histories lurking beneath ordinary language,” and so too is Sestanovich’s prose. She describes the “currency of secrets” as “loose change that could add up to something valuable”; rain is “relentless, monotonous – all form, no content.” Some aphorisms lack the grounding of her best metaphors: “Maybe you can only love someone without knowing you do,” Eva says to the AOC stand-in as if it were a revelation. But she’s more affecting when she’s documenting the granularity of her characters’ surroundings, like “leafless trees strangled by Christmas lights” and a “sidewalk’s overbite,” than in vague meditations on the nature of love. While Sestanovich’s reach sometimes exceeds her grasp, it’s reaching that she’s more curious about anyway.

At the newspaper, Eva starts working with a curmudgeonly advice columnist. “People will tell you that they read advice columns for the advice. … They’re wrong,” she tells Eva. “They care about the questions, not the answers.” Eva, endowed with the knowledge that everyone is really after others with similar problems, starts writing back to some readers when the columnist retires. Sestanovich’s novel, in turn, wants to take us from contemporary culture’s ever-proliferating answers to its relative dearth of worthy questions. The answers don’t necessarily matter, so long as the questions are asked in good faith.

Ariella Garmaise is an assistant editor at the Walrus. Her writing has been published in the Los Angeles Review of Books, LitHub and other publications.

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