Wedding Daze (2006)

After losing the woman of his dreams, Anderson is convinced he'll never fall in love again. But at the urging of his best friend, he spontaneously proposes to a dissatisfied waitress named Katie and an innocent dare evolves into the kind of love that both have been looking for all along.

Director:

Michael Ian Black

Stars:

Jason Biggs (Anderson), Isla Fisher (Katie), Michael Weston (Ted), Ebon Moss-Bachrach (Matador), Joe Pantoliano (Smitty), Heather Goldenhersh (Jane)