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.
Despite being furious with Molly for raising her hopes, 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 admonishes him for only caring 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 comatose father, 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. But one night, after fighting with and feeling hurt by Neal again, Molly spends the night with Ray after feeling alone at Huey's apartment and finds Neal one morning, having slept with Roma. However, after a fight, Ingrid kicks Molly out, and Molly goes to live with Huey. Disgusted, Molly agrees to Ingrid's suggestions to sell off her possessions 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.
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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 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 her misfortune, she finds out that her father's accountant embezzled all 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 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 fun-loving and free-spirited woman who lives off the ample trust fund of her late rock legend father, Tommy Gunn.
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