She is surprised when Ray dances freestyle to Neal singing "Molly Smiles", a classic written by her father when she was a child. Molly arrives to Ray's recital late and is pleased to see Ray is wearing the tutu Molly designed for her earlier. She promises to stay friends with Ray and enrolls in design school after realizing her talent for fashion. She and Ingrid also make up and Molly finds Ray to apologize as well.
At the wake for Ray's father, Molly meets other musicians who ask her to design their clothes after seeing Neal's jacket in his video. Molly, deciding to take charge of her own life, takes Ray's advice to auction off her late father's guitar collection to an unknown buyer this enables her to afford her own place. At first, Ray tries to be angry with Molly for raising her hopes but then she collapses into Molly's arms, crying, finally coming to terms with her grief. Molly finds Ray at Coney Island, riding in the tea cups. Ray runs away from home and Roma begs Molly to find her. Molly turns him down and coldly tells him that he is selfish and only cares about her when she can give him something. As she leaves, Molly bumps into Neal, who begs to get back together as she was his whole inspiration. In Roma's office, Molly calls Roma out for never paying attention to her daughter. However, Ray's father dies the next day, and Ray tells Roma to fire Molly. She encourages Ray to talk to her father, even though he is in a coma and promises that it will help him improve. The budding friendship between Molly and Ray continues to develop when Molly takes Ray to Coney Island and explains that when her parents died, she ran away to Coney Island and rode the tea cups.
However, after a fight, Ingrid kicks Molly out to live with Huey. Disgusted, Molly agrees to Ingrid's suggestions to sell off her possession so she can prove that she is growing up. Soon after, he gets a record deal with Roma and has a hit music video with a song that Molly inspired him to write, all while wearing the jacket Molly made. She redesigns it to fix the damage but Neal breaks up with Molly when he sees it, claiming he has to pursue his music career and does not have time for her flightiness. After a baking accident, Molly causes a fire that damages Neal's jacket. Molly continues to pursue Neal and holds onto his lucky jacket in hopes of seeing him again.
Although she enjoys ballet, she refuses to freestyle and often quotes Mikhail Baryshnikov: "Fundamentals are the building blocks of fun." Molly attempts to show her how to have fun, which at first causes much conflict between them, but eventually Ray opens up to let Molly in. Ray's father is in a coma and is being treated at home by a private nurse which causes Ray to stifle her emotions to maintain order. Molly begins work as a nanny of an eight-year-old hypochondriac and neat freak named Lorraine "Ray" Schleine ( Dakota Fanning) who is the daughter of Roma Schleine ( Heather Locklear), a music executive who is too busy to notice Ray. She moves in with her best friend, Ingrid who tells her that in order to stay with her, she must find a job. Adding to Molly's misfortune, she finds out that her father's accountant embezzled her money, so she is left penniless and homeless. They have a night of passion but he leaves in the morning, saying that he can't stay in Molly's carefree life. Molly falls for singer Neal Fox ( Jesse Spencer) when he plays at her birthday party thrown by her best friends, Huey ( Donald Faison) and Ingrid ( Marley Shelton). Molly Gunn ( Brittany Murphy) is a carefree and fun-spirited girl, living off the ample trust fund of her late rock legend father, Tommy Gunn.