Steve Pink Director Justin Long Bartleby Gaines Actor Jonah Hill Sherman Actor Blake Lively Monica Actor Maria Thayer Rory Actor Lewis Black Uncle Ben Actor Adam Herschman Glen Actor Anthony Heald Dean Richard Van Horne Actor Columbus Short Hands Actor Travis Van Winkle Hoyt Ambrose Actor Diora Baird Kiki Actor Mark Derwin Jack Gaines Actor Ann Cusack Diane Actor Hannah Marks Lizzie Gaines Actor Kellan Lutz Dwayne Actor Brendan Miller Wayne Actor Robin Taylor Abernathy Actor Mark Perez Writer Adam Cooper Writer Bill Collage Writer Tom Shadyac Producer Michael Bostick Producer Brian Lutz Executive Producer Louis G. Friedman Executive Producer Mark Perez Executive Producer Matthew F. Leonetti Cinematographer Scott Hill Film Editing David Schommer Original Music Rusty Smith Production Design Denise Hudson Art Director Sara Andrews Set Decoration Genevieve Tyrrell Costume Design Joseph Middleton Casting