Guest Stars Pico Alexander as Josh Caleb Lowell as Tyler Kosha Patel as Sunita Sule Thelwell as Desmond Melissa Juliet Lawson as Olivia / Other Girl Joshuah Melnick as Wes / Hacky Sack Terralon Walker as Bery / Babysitter Amy Gordon as Holly / Hyper-Fit Woman Charlie Bodin as Older Tyler Co Starring Tricia Paoluccio as Jamie / Darien Mom Brandiss Lashai Seward as Ms. Vincia Maury Ginsberg as Brett / Darien Dad Amanda Morris Hunt as Edwin's Sister