Mona Simpson's 'Casebook,' Will Shoot You Back to Childhood With Nuance, Grace, and Humor

Remember what it was like to be nine years old? For most, we were too busy daydreaming of our first crushes to know just how crazy we were driving our parents. But we were also just starting to make deeper attempts at understanding the enigma of adult relationships.

With her latest novel, Casebook (Knopf), award-winning author Mona Simpson shoots us back to this naïve enlightenment, exploring modern childhood through the complex psyche of an adolescent boy grappling with a dismantled family and his own sense of alienation in the aftermath of divorce. Bringing that same emotional electricity she established with her stunning debut Anywhere But Here, Simpson once again delivers an eloquent portrait of fraught parent-child relationships, crafting a story that is both tenderly comical and deeply moving.

Casebook, which adopts a story-within-a-story framework with a first-person, diary-like format, spans the length of Miles Adler-Hart's pre-teen to college-age years. The novel opens with 9-year-old Miles hiding beneath the dusty box spring of his parents’ bed. He's hoping to eavesdrop on a conversation about Survivor, the über-popular reality show he isn’t allowed to watch. Instead of an episode recap, however, he overhears an intimate confession: His parents admit that they have fallen out of love. For Miles, the startling news sets in motion a marathon of epic sleuthing as he attempts to gather clues — eavesdropping on conversations behind closed doors, listening in on phone calls via a rigged extension, spying on his mother’s therapy sessions through secret crawl spaces, and rummaging through private drawers — in order to piece together the mystery of his parents’ failed marriage and their new post-separation romances.

While the novel takes off a bit clumsily and it takes a few chapters for the young narrator's voice to sound authentic, Simpson eventually finds her narrative footing and succeeds at crafting a genuine adolescent protagonist, sensitive and vulnerable. Miles's keen observations, internal revelations, and comical musings are delivered in a voice that poignantly fluctuates between childlike naivety and adolescent precociousness as he attempts to navigate the social clumsiness of middle and high school life alongside the rocky emotional terrain of a disintegrating family.

“We had what we’d had before, but less of it,” Miles says when his father comes over for their first post-separation Christmas dinner. “We were still working out our new life. Our family couldn’t reassemble; even I understood that whatever held people was fragile and, once broken, couldn’t be put together again. But we weren’t something else yet.”

At the heart of the novel is Miles's relationship with his mother, a brilliant mathematician whom he affectionately calls “the Mims.” “I’d woken up at odd times in the night to her crying. I never told that I heard,” he says of the Mims. “A measure of her despair was the fear that she was failing us.”

As Miles watches his mother’s emotional strength weaken in the midst of marital failure, he becomes increasing protective of her. His true sleuthing begins when he becomes leery of her clingy, yet elusive new love interest, Eli Lee, “the dork guy.” With the help of his best friend Hector, Miles advances his spying techniques, purchasing wiretaps at a local spy shop, hacking into the Mims’ emails, and eventually enlisting the aid of a celebrity private investigator whose ad Hector discovers in the classifieds.

Charming scenes of upper middle class domestic life and candid teenage antics add humor and color to Simpson’s affecting coming-of-age story. The family attends holiday vacations in the mountains, multi-family picnics at the beach, and weekly neighborhood dinner gatherings, while Miles and his friends establish Friday night sleepover traditions, host clandestine viewings of rated-R movies, concoct revenge plots targeted at deceitful boyfriends, and devise money-making schemes selling soup during school lunch hour.

Miles's relationship with various father figures, too, contribute to the novel’s emotional pulse, each affecting Miles in different ways. Feeling increasingly distanced from his father, who seems increasingly preoccupied with his social life, Miles quickly discovers an adult confidant and mentor in Ben. When their investigation finally leads to the unmasking of Eli's true character, Miles is heartbroken alongside his mother; the emotional effects of such deception leads to personal revelation by all characters involved.

“All of a sudden love seemed like a flimsy thing,” Miles says at one point, and then at another: “Love ruined people’s lives, the way our parents said drugs could.”

With her seasoned pen, Simpson is a master at capturing the nuances of teenage psyches and fraught family relationships, spinning their intricate emotional fabrics into elegant prose. While she is mining time-worn topics, her impressive ability to articulate adolescent angst makes Simpson's work sing. Casebook is a moving portrait of domestic dysfunction and the anxieties that beset the modern child — one that pays tribute to the emotional complexity and strength of children and the ways in which our families, as tangled and flawed as they often are, shape and define us.