Guest Stars Ben Rappaport as Max Horowitz Heidi Armbruster as Michelle Noah Robbins as Bryce Reiger Krysta Rodriguez as Kim Co Starring Anastasia Barzee as Claire Polly Lee as Leslie Khoa Nguyen as Guy #3 Dana Cuomo as Joanne Libby George as June Branden Wellington as Guy #2 Jennifer Simard as Sherry Darren Cerullo as Helicopter Ground Crew Tim McKiernan as Guy #5 Mike Heslin as Guy #1 Jon Sprik as Guy #6 David Windmiller as Ryan (Pilot)