Molly Gunn, portrayed by Brittany Murphy, lives a seemingly charmed life, embodying the spirit of a fairytale princess. Her carefree existence is rooted in a tragic past; her rock-and-roll father died in a plane crash alongside her mother when Molly was just a child. On her birthday, in a bustling nightclub, she encounters Larraine "Ray" Schleine, played by Dakota Fanning, a well-organized yet anxious young girl who struggles with hypochondria. Ray is the daughter of Roma Schleine, a prominent record label owner portrayed by Heather Locklear.
At the nightclub, Molly also crosses paths with Neal, an ambitious Australian singer played by Jesse Spencer, who hopes to land a record deal with Roma. Captivated by Neal, Molly invites him back to her home after the party. As she reveals her late father's impressive guitar collection, Neal's interest quickly wanes due to Molly's quirky personality, which includes a pet pig named Mu and her unexpected love for Pez. His disinterest leads him to choose his musical pursuits over his feelings for Molly, leaving her heartbroken but determined to win him back.
Soon after, a financial blow strikes: Molly's accountant absconds with her $100 million inheritance. Faced with overwhelming debts, she realizes she must seek employment despite her lack of experience or skills. She temporarily relocates to live with her supportive best friend, Ingrid, played by Marley Shelton, who insists she find a job to stay in her apartment. Ultimately, Molly gets hired as Ray's babysitter, stepping into Ray's extravagant life, where she navigates a stark contrast to her own outlook.
Initially, Ray’s stoic demeanor and disdain for Molly's playful attitude create friction between them. During a dish-washing incident, their conflict escalates, highlighted by the tense exchange: "When you work for me, you leave when I say you can leave." When Molly quips that she works for Ray's mother, Ray counters that due to her mother's constant absence, Molly is effectively under her jurisdiction. In a fit of frustration, Molly attempts to quit, giving herself a bloody nose as she storms out.
While Ray clings to rigid routines in an attempt to cope with her father's coma, quoting, "Fundamentals are the building blocks of fun," she struggles to balance her need for control and her passion for ballet. After their heated confrontation, Molly reconciles with Ray at ballet class, presenting her pig Mu as a peace offering. Though their dynamic is rocky, they venture to Coney Island, only to find it closed for the season.
As they journey home on the subway, Molly opens up about the tragic loss of her parents, highlighting vulnerable moments that deepen their bond. However, the next morning reveals a stunning betrayal when Molly discovers Neal, the man she fell for, is entangled with Roma in pursuit of his career ambitions. After learning of Ray's father's passing, Molly attempts to support her friend, yet is met with Ray's unsettling indifference toward her grief.
When Molly confronts Roma about her lack of genuine involvement in Ray's life, she expresses frustration at Roma’s superficial parenting. Acknowledging the dire financial situation, Molly sells her father's cherished guitar collection to make ends meet.
In a twist of fate, Molly is eventually contacted by Roma regarding Ray's disappearance. After a desperate search, she finds Ray in an amusement park, and they share an emotional reunion that begins their path to healing. Molly’s compassion draws Ray out of her shell, leading to a significant turning point.
Attending the funeral of Ray's father, Molly witnesses a noticeable change in Roma as she begins to take more interest in her daughter. On a hopeful note, Ray confides in Molly about their newly forged friendship, dismissing the notion that adults and children can’t be friends. Meanwhile, Molly pursues her dreams by applying to the Fashion Institute of Technology, receiving promising responses.
As Ray's ballet recital nears, she adorns the tutu crafted by Molly, while Neal makes a surprise appearance, performing "Molly Smiles," a song penned by her late father. The recital culminates in a display of joy as Ray embraces freestyle dancing, leaving Molly in the audience beaming with pride. The poignant moment is encapsulated in Ray’s reflective words: > "Every story has an end. But in life, every ending is just a new beginning."
