On Long Island in 1961, the story centers around a young girl named Alice Bloom, played by Eliza Dushku, who is just 10 years old but already harboring a strong fascination with her older neighbor, Sheryl O'Connor, portrayed by Juliette Lewis. Sheryl, a 17-year-old girl, lives across the street from Alice, and their worlds are vastly different yet intertwined through a mixture of admiration and longing. Alice frequently spends her time watching Sheryl from her bedroom window, becoming obsessed with every detail of her life — from her perfume to the records she listens to — eager to emulate everything about her.
Sheryl appears to live a life of youthful independence, often showing affection that Alice yearns to understand. Alice admires the love and attention that Sheryl's father gives her, a stark contrast to her own relationship with her own father, played by Michael Stephen Costello, which is more distant and cold. Alice’s infatuation grows as she copies Sheryl's mannerisms, clothing, and even her choice of music, which shows her deep desire to be connected to her.
One day, Alice encounters a rougher reality when her friends at the local bowling alley tease her — a painful moment that underscores her loneliness and vulnerability. That same day, she witnesses Sheryl walking into the alley with a group of guys, trying to attract their attention and win their approval. Despite her innocent and moral stance, Sheryl is courted by Rick, a charming young man played by [C. Thomas Howell], who works as a counter boy at the alley. Their mutual attraction sparkles early on, setting the stage for a complex relationship.
While Alice continues to observe Sheryl and Rick’s interactions, she remains firmly on the sidelines, her admiration turning into a secret fascination. During one encounter, Rick pages Sheryl to return to the alley’s desk, only for an officer to inform her that her father has tragically died. Sheryl is visibly upset during the funeral, mourning her loss and the complicated emotions that come with it.
That evening, as Sheryl returns her bowling shoes, she breaks down in tears over her father's passing. Soon after, Rick walks her home, and their connection culminates in their first kiss, which Alice witnesses with a mixture of innocence and longing. Their budding romance intensifies when Rick and his friends take Sheryl to the beach, where they spend hours sharing oysters and tequila, and Sheryl pours her heart out over her father’s death and her own feelings of loss and confusion. The day turns into a full-night adventure, reinforcing their deepening bond.
However, the relationship faces obstacles when Sheryl's mother, portrayed by Helen Shaver, disapproves of her daughter’s relationship with Rick. Despite her mother’s objections and societal gossip, Sheryl refuses to back down and continues to see Rick in secret. During this time, Sheryl and Alice develop a close friendship, with Sheryl offering Alice advice about boys and life. Alice, eager to help, even plans to assist Sheryl in sneaking out to meet Rick, leading them into a series of secret, sometimes seedy adventures—visits to dive bars and nights under the boardwalk, which Alice captures in a recording booth as a memento of their escapades.
As Sheryl's pregnancy becomes evident, her mother swiftly sends her away to an unwed mother’s home, located 300 miles from Long Island. Rick, determined to stay connected, calls her repeatedly, but her mother dismisses his calls. In a passionate effort, Rick and his gang drive to Sheryl’s house, only to be turned away by her mother. This confrontation turns violent when Rick pushes past her to get inside, causing neighbors to intervene in a brawl that results in Rick spending a week in jail.
The upheaval causes Alice to feel increasingly withdrawn. Motivated by her concern, she decides to run away. Rick finds her under the boardwalk and they have an emotional conversation, during which Rick agrees to travel upstate with Alice to find Sheryl at the unwed mother’s home. Eventually, Alice successfully persuades Sheryl to sneak out at midnight to meet Rick once more. Although Sheryl has made the difficult decision to put her baby up for adoption because she feels she cannot build a future with Rick and their child due to their limited resources, Rick offers her a pawned engagement ring, symbolizing their love and hope for the future.
In a heartfelt discussion, Sheryl confides in Alice, telling her that true love isn’t always simple or easy. Despite her young age, Alice understands the gravity of what’s happening. She still dreams of a life where they can escape their troubled circumstances. However, Sheryl insists she must stay with her family, even as her bus departs for Long Island. She watches Rick and Sheryl embrace at the bus station, knowing that their paths are diverging but hopeful about their future.
When Alice returns home, her parents are relieved to see her safe again. She reflects on the gossip surrounding her friend and the challenges girls face in her community but finds solace in receiving a postcard from Sheryl — one that confirms she and Rick are traveling westward, beginning anew and doing well. This story, filled with youthful innocence, love, heartbreak, and the enduring bonds of friendship, paints a vivid picture of teenage life and the undeniable power of hope amid difficult circumstances.
