Nate Cooper (Joel David Moore) just can't get it together with women. But he also can't forget his first crush, Cristabel Abbott (Paris Hilton), from their time in elementary school, the first grade. He sets out for the beaches of California and meets up with his geeky best friend, whose mom has an unnatural amount of information about Cristabel, and perhaps an unusual relationship with her son.Cristabel jogs on the beach every day with many suitors trying to catch her eye, including an albino stalker. But she's still single, and there is a reason: Cristabel is still best friends with the same ugly little girl Nate knew from first grade, June Phigg (Christine Lakin).
Nate manages to reintroduce himself to Cristabel and they surprisingly hit it off. However, Cristabel refuses to go on a date with Nate unless June has a date as well. Nate sets out to find a boyfriend for June, but guys recoil at the sight of her. At the Santa Monica Pier, Johann, an attractive dentist who works as a part-time model, appears in their lives. He seems to want to do a makeover on June. As Nate and June become friends and she emerges from her cocoon, Nate slowly realizes that the girl of his dreams may be June.
The story contains flashbacks to Valentines Day first grade when Nate creates a Valentine for Cristabel but ends up giving it to June when he realizes how lonely she is. Finding the Valentine in June's drawer makes him realize that she was the right person for him all along.
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