The Best Friend is Bowler’s unnamed closest friend. She is a recurrent figure throughout the memoir, as Bowler incorporates consistent anecdotes from their shared experience and life together. The Best Friend is a constant in Bowler’s life: The two met in college and have remained close ever since. While the Best Friend consistently shows vulnerability—as displayed in her ongoing challenges with her male friend—she is also a source of strength for Bowler. Bowler relies on the Best Friend, who often acts as a sounding board, for support and companionship.

Bowler frequently conveys her ideas and questions to the Best Friend to make sense of her internal struggles. The narrative repeatedly depicts them taking long walks together or engaging in lengthy phone calls or esoteric discourses. Bowler also depicts the Best Friend sitting by her side in the emergency room, talking to her bluntly about her journey with cancer, and waking her in the middle of the night to sneak out and bless her old house. Such anecdotes add texture to Bowler’s overarching narrative, while illustrating the Best Friend’s ability to help Bowler engage in reality. The steady nature of the Best Friend’s presence throughout the memoir is significant, given Bowler’s heavy incorporation of other male thinkers, professionals, and acquaintances. The Best Friend’s presence offers a raw, emotional counterpoint to the memoir’s other more rigid, fact-based presences. Recurrent images of Bowler in conversation or interaction with the Best Friend also serve to humanize Bowler to the audience.

Toban and Zach are Bowler’s husband and son. Like the Best Friend, they are also recurrent figures and offer personal and vulnerable insight into Bowler’s private life. Throughout the memoir, Bowler expresses blatant frustrations with her husband or details befuddling interactions with her son. Such moments illustrate who Bowler is as a person, depicting her in the more grounded moments of daily life. Anecdotes surrounding her and her son’s bedtime rituals or her and her husband’s arguments about packing or Pickleball present Bowler beyond her credentials. She is a wife and a mother, as well as a thinker, historian, theologian, professor, and author.

Ronald Rolheiser is a Canadian Roman Catholic priest, theologian, and author on Christian spirituality. As a longtime columnist and former president of the Oblate School of Theology, he is a significant voice in translating academic theology into pastoral guidance for contemporary life. In Joyful, Anyway, Bowler incorporates Rolheiser’s theological insight into her own explorations; his ideas offer a framework that allows Bowler to move from resisting her grief to embracing it as a necessary spiritual practice. He gives her a vocabulary to understand longing not as a personal failure but as a sacred part of the human condition.

Rolheiser’s primary contribution is to reframe “the ache” as a “divine fire” (72) or a “holy longing” (72). This concept transforms a source of private shame into a shared, spiritual reality. He argues that this perpetual disquiet is not a mistake to be fixed but the very energy that points toward God. His most pivotal advice gives the book its essential pastoral direction: “But if you can mourn it, you can live with it” (76). This simple statement unlocks Bowler’s argument surrounding The Necessity of Processing Grief and Pain, suggesting that acknowledgment is the path to living with unfulfilled hopes. He anchors this wisdom in a broader Christian theological tradition, citing thinkers like Karl Rahner to affirm that in this life, there is “no finished symphony” (74).

Bowler’s interview with Rolheiser marks a significant turning point in the memoir’s overarching arguments. His teachings provide Bowler with the intellectual and spiritual permission for her to shift her focus from seeking a cure for suffering to developing practices for mourning. This interaction validates her move toward a more realistic, ritual-centered spirituality that makes space for both sorrow and the eventual return of joy.

Jerry Sittser is an American theologian and professor emeritus whose work on grief is grounded in catastrophic personal loss. In 1991, a drunk driver caused a collision that killed his mother, his wife, and his young daughter. His subsequent book, A Grace Disguised (1996), has become a foundational text for modern Christian understandings of suffering and resilience. For Bowler, Sittser’s experiential authority models a form of faithful realism that learns to live within the tension between sorrow and hope.

Sittser’s key insight helps Bowler recalibrate her expectations about recovery and faith. He teaches her that even divine interventions are not permanent fixes, a lesson that directly challenges the miracle-thinking prevalent in American culture. “I mean, Lazarus did die again,” Sittser explains. “And that is the dirty little secret about miracles … they don’t last” (230). His perspective encourages a shift from seeking a single, transformative event to cultivating durable, everyday practices that can sustain a person through ongoing loss. He provides Bowler with a way to hold hope and sorrow together without letting one cancel out the other.

Sittser contributes the metaphor of an “aperture” to describe this dynamic. He explains that after loss, the aperture of the soul opens and closes to the light, and wisdom lies in attuning to this natural oscillation. This image gives Bowler a way to frame joy not as something that arrives intermittently, even amid pain and constraint. Sittser’s testimony, shared in an interview with Bowler, enriches her critique of a culture that often demands a swift and complete recovery from grief.

Granville Oral Roberts was a pioneering American televangelist and a central figure in the mid-20th-century Charismatic movement. As the founder of a massive faith-healing ministry and Oral Roberts University, he was an architect of a religious culture that linked faith directly to tangible blessings like health and prosperity. In Joyful, Anyway, Roberts functions as the historical embodiment of the miracle-thinking that Bowler critiques.

His famous exhortation, “Expect a miracle” (227), encapsulates the ethos of guaranteed outcomes that Bowler identifies as a form of toxic positivity. This mindset suggests that faith can and should override the natural order, promising believers a cure for every ailment and a solution to every problem. Bowler presents his unwavering promises as the antithesis of a faith that makes room for grief, uncertainty, and unfulfilled longings. The controversies surrounding his fundraising and claims of divine intervention further serve to highlight the spiritual and emotional risks of a belief system that frames hope as a predictable payoff for faith.

Jack London, the celebrated American author of classics like The Call of the Wild (1903), serves as a cultural case study in Joyful, Anyway. An icon of rugged individualism and relentless adventure, London’s life represents the American myth of boundless striving and self-invention. Bowler uses him to critique the “go, go, go” (43) ethos that equates a meaningful life with an ever-expanding list of experiences.

A visit to London’s former ranch, now a state park, sparks Bowler’s reflection on his famous credo: “I would rather be ashes than dust!” (42). While acknowledging its inspirational power, she reads this philosophy against the quiet obligations and duties he left behind, particularly his first wife and two daughters. London’s life of adventure maximalism is contrasted with Bowler’s developing ethics of limits, mourning, and commitment to place. He becomes a symbol of a totalizing pursuit of personal fulfillment that often comes at a high cost to others, allowing Bowler to clarify her argument for a different, more grounded vision of a good life.