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Harold Reynolds (Spencer Breslin) is a 13-year-old boy with early male pattern baldness. Harold seems to cope all right in his hometown, Douglasburg, until his mom, Maureen (Ally Sheedy), announces that they are moving to a new house in a new town. Harold panics because he had somewhat fit in with everyone at his old school, despite his baldness.When he arrives in his new house, he is met by an elderly new neighbor, Maude (Suzanne Shepherd), who assumes Harold is older because of his baldness, and starts flirting with him. Harold starts at his new school, and because he initially wore a hat into class, he was seemingly accepted, especially by a girl, Evelyn (Elizabeth Gillies), who he briefly flirts with. When the teacher, Ms. Vicki Norris (Rachel Dratch), notices him wearing a hat, he is forced to take it off, thus revealing that he is bald. Instantly he is ostracized by the other students, including Evelyn.Harold's older sister, Shelley (Stella Maeve), has started High School in the new town as an immensely popular and flirty cheerleader. She meets a boy named Patrick (Robert Gorry) and they quickly start dating, which leads Patrick assuming that Harold is Shelley's father. Patrick asks Harold to buy some beer for him and his friends, which works multiple times.Harold is being bullied relentlessly by students. One of the few nice people is Cromer Styles (Cuba Gooding, Jr), the school janitor. While in gym class, the bullying rears its ugly head and the Coach (Chris Parnell) joins in. Cromer comes to the rescue when he announces Harold is wanted in the office. That was just a decoy - Cromer and Harold watch TV in the janitor's room.Harold returns home, angry and upset, and decides to go back to his old home, where everyone liked him. He leaves late at night so that his Mom and sister won't get suspicious. He only makes it as far as a strip bar. Harold thinks that because he looks older, he may pass for legal age, but Cromer is there as well, and he takes Harold home. He gives Harold words of encouragement, and then drops him off at home.The next day in gym class, Harold is asked to take his shirt off as part of the Skins and Shirts team. He has a big strip of hair on his back, and everyone starts laughing at him. He talks to Cromer, and they decide to pull a prank on the coach, turning off the hot water when the coach is in the shower.