In 1961, 11-year-old Beverly "Bev" Donofrio rides alongside her father, Leonard, who is a police officer in Wallingford, Connecticut. Eager to attract a boy's attention, she requests a bra for Christmas, but he responds that she is too young and should prioritize her studies.
By 1965, the bright yet innocent Bev aspires to attend college in New York City to pursue her dream of becoming a writer. At a party with her friends, Fay and Tina, she finds herself in an awkward situation when Bobby, Fay's older boyfriend, is set to be deployed to Vietnam. Heartbroken, she delivers a love letter to the popular boy, Sky, who cruelly reads it aloud, prompting her to take refuge in the bathroom. It's there that she meets Ray, a stranger who defends her honor in a fight against Sky.
Bev and Ray, along with Fay and Bobby, escape the party to a lookout point where the couples share intimate moments. Bev is charmed by Ray's kindness, leading them to cross a line of innocence. They are caught by Leonard during a police patrol, yet Bev cleverly insists that they merely shared a kiss.
The situation becomes more complicated when Bev informs Ray of her pregnancy; initially reluctant to marry, she eventually agrees to a hurried wedding to appease her parents. At the reception, she feels isolated as her friends and family avoid her. In a surprising turn, Fay announces her own pregnancy, leading to a shift in their futures as they both contemplate the trials and triumphs of impending motherhood.
Despite the celebrations, they mourn the loss of their adolescent dreams, including prom and education. When Bev gives birth to a son, Jason, she struggles with her feelings as she had initially hoped for a daughter. Nevertheless, she continues her studies, balancing motherhood with her ambitions. However, a college scholarship interview proves challenging as she navigates her responsibilities with a young child in tow.
As the years pass, Bev finds herself grappling with new challenges. When Jason almost drowns at a friend's birthday party, she resolves to be more attentive, yearning to reclaim the childhood experiences she missed out on. Eventually, news of Fay's divorce hits hard, leaving both women in a precarious state as they consider their futures.
Years later, Jason's birthday party brings former classmates together, igniting old flames and aspirations as his friends, like Tina, move on with their lives. An unexpected suggestion from Tommy gives Bev hope about moving to California for her education, but complications arise when Ray reveals he has become a heroin addict, squandering their savings. After a tumultuous realization, Bev opts to end their relationship and focuses on being a supportive mother.
Two years later, with the help of Fay, the resourceful mothers attempt to make ends meet, but their troubles mount when their actions lead to their arrest. Blaming Jason for their predicament adds strain to their already fragile relationship.
In 1986, Bev embarks on a journey to reconcile with Ray, now hoping to get him to sign off on her memoir. Yet, amidst the unveiling truths about their past and her ambitions, Jason reveals his wish to transfer schools to join his girlfriend, Amelia. This revelation sends Bev down a spiraling path of self-realization and guilt.
After a heated exchange where Jason calls her selfish, she is stirred by his words and recognizes her sacrifices. The warmth of their shared bond leads her to express pride in him, ultimately leading to a pivotal moment where she gives him her car to help support his dreams in Indiana.
In the end, as Bev drives away with her father, she reflects on her relationship with Jason and the weight of her choices. Singing together, they navigate through their shared heartbreak, acknowledging not just the past but also the promise of new beginnings.
