Boys and Girls (2000)

A friendship is put to the ultimate test when two best friends wind up in bed together.

Director: Robert Iscove

Cast: Freddie Prinze Jr., Claire Forlani, Brendon Ryan Barrett, Gay Thomas Wilson, Raquel Beaudene, David Smigelski, Blake Shields, Alyson Hannigan, Jason Biggs, Amanda Detmer, Sean Maysonet, John X Volaitis, Tsianina Joelson, Kristofer Mickelson, Matt Carmody, Heather Donahue, Richard Hillman, Tim Griffin