Guest Stars Pico Alexander as Josh Caleb Lowell as Tyler Kosha Patel as Sunita Sule Thelwell as Desmond Matthew Risch as Greg / Mr. Decorator Matthew Lawler as Todd / Tyler's Dad Terralon Walker as Bery / Babysitter Bryan Terrell Clark as Paul / Dr. Dermatologist Co Starring Melissa Juliet Lawson as Olivia / Other Girl Joshuah Melnick as Wes / Hacky Sack Tricia Paoluccio as Jamie / Darien Mom Amy Gordon as Holly / Hyper-Fit Woman Brandiss Lashai Seward as Ms. Vincia Maury Ginsberg as Brett / Darien Dad Amir Henderson as Young Edwin Merionne Toussaint as Stephen / Manager Zani Jones Mbayise as Young Sara Lycott Amanda Morris Hunt as Edwin's Sister Judah Edwards as Young Gogo Chance Smith as Young Desmond Constance Zaytoun as Dr. Norton Kiana Lynn as Young Bery