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The most notable and successful of them involve flashbacks to Josie's early high school years as well as a scene set in the present where she unknowingly manages to have the word "loser" printed on her forehead as she walks around her high school much to the delight of the other students.Unfortunately, such moments are few and far between.Beyond Barrymore's fun take, the film's other performances are delivered with mixed results.
They hit it off and Henry think he's finally found the girl of his dreams, until he discovers she has short-term memory loss and forgets him the next day. But then she breaks the most important rule of all: she falls in love with the groom. Josie, who was a frustrated, ridiculed nerd, gets a popular make-over from her drop-out, naturally funny brother Rob Geller. But in Josie's case, it's sensitive bachelor teacher Sam Coulson, who enjoys sophisticated conversation.
Nearly everyone, at some point in their lives, has looked back on their past and thought, "If I only knew then what I know now," particularly relating to their often turbulent high school years.
With such hindsight and a time machine, one could go back and pay more attention and thus get better grades, participate more and definitely be more popular.
It's not until her brother Rob (DAVID ARQUETTE), a guy who works in a packaging store whose life hasn't improved since his school days, reminds her that she was a complete geek in high school and that everyone called her "Josie Grossie." Nonetheless, and trying her best to fit in as a teenage student, Josie enrolls in South Glen South High School.
Her efforts are immediately thwarted, however, by her clueless sense of style that causes other students to pick on her, such as a trio of snobbish girls, Kirsten (JESSICA ALBA), Kristen (MARLEY SHELTON) and Gibby (JORDAN LADD), and the school's resident hunk, Guy Perkins (JEREMY JORDAN), who reminds her of her former, but unreciprocated high school crush.
A washed up singer is given a couple days to compose a chart-topping hit for an aspiring teen sensation.