The Hottie & the Nottie (2008)

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 short, unattractive brunette girl whom Nate also knew in elementary school, June Phigg.

Nate reintroduces himself to Cristabel and they 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. One day at the Santa Monica Pier, Johann Wulrich, an attractive dentist who works as a part-time model, appears in their lives. He seems to want to do a makeover on June when he apparently sees her inner beauty. However, Nate believes that Johann is a threat to his shot for Cristabel, since Johann is almost perfect. Eventually, with June dating Johann, Cristabel finally begins dating Nate, per his original plan.

Over the next few weeks, as Nate and June become friends and she emerges from her cocoon, with her face and appearance transforming into that of an attractive woman whose beauty begins to compare with Cristabel, Nate slowly realizes that June may be the girl of his dreams. Nate tells this to Cristabel, who is happy for June. Nate then tries to find June, and finds her, telling her how he feels.