During his fifth-grade year, ten-year-old Josh Beal [Joseph Cross] Beal begins a personal search to understand life and death — a journey sparked by the passing of his beloved grandfather Robert Loggia. He attends Waldron Mercy Academy, a private Catholic boys' school in Philadelphia, where the routine of uniforms and strict rules makes him feel small and sometimes overlooked; he often finds himself bullied because he is small for his age. His best friend Dave [Denis Leary] becomes a constant companion in mischief, always looking for a way to cut class, while Josh quietly navigates the ache of losing his grandfather and the sense that he’s not entirely in safe hands.
Motivated by grief, Josh launches a personal mission to find God and meaning in a world that now feels fragile and uncertain. Along the way, he finds unlikely guidance from two sources: Dave and a Philadelphia Phillies–loving nun Rosie O'Donnell who teaches at Waldron. Dave even engineers a distraction that allows Josh to slip into the girls’ school to meet a cardinal, hoping this encounter might illuminate his faith; but standing face-to-face with the cardinal reveals to Josh the human frailty that even revered figures carry.
Josh also pursues a dream he believes could bring him closer to understanding the divine: he asks his family to travel to Rome during the winter break, a proposal his parents see as part of his faith quest and quickly reject. In the midst of this earnest search, a girl named Hope Julia Stiles enters his world, becoming his first crush and a source of gentle light amid his trials. They cross paths again at a boy’s birthday party, and Josh musters the courage to share his feelings. Later, at a ceremony where the girls’ school offers flowers to the Virgin, Hope gives Josh a rose, a small yet meaningful symbol for his quest.
As the school year unfolds, a string of incidents among Josh’s classmates tests his resolve and sense of justice. One student unexpectedly kidnaps the school’s framed portrait of the pope, a startling act that unsettles everyone. The bully at Waldron faces consequences and is forced to leave the school due to financial issues, highlighting the precariousness of adolescence and the fragility of reputations. After an awkward moment where he finds himself stuck in a turnstile with a boy named Frank, the bully agrees to spend more time with Josh and Dave, underscoring the slow process of friendship and empathy. And throughout it all, Josh’s dream of faith, doubt, and understanding continues to evolve, with Dave facing a serious personal health challenge when he is diagnosed with epilepsy.
