The Hottie & The Nottie (2008)

Nate moves to L.A. to track down Cristabel, the woman he’s been in love with since childhood, only to discover that his plan to woo her only has one hurdle to overcome: what to do with June, Cristabel’s ever-present, not-so-hot best friend? What’s even more complicating is Nate’s growing feelings for June, whose true beauty starts to emerge.
Tom Putnam, John Lind, Nila Neukum, Michael D. Gillis
Paris Hilton, Joel David Moore, Christine Lakin, Johann Urb, Adam Kulbersh, Greg Romero Wilson, Marianne Muellerleile, Kathryn Fiore, Morgan Rusler
tt0804492