Guest Stars Pico Alexander as Josh Kosha Patel as Sunita Caleb Lowell as Tyler Sule Thelwell as Desmond Matthew Risch as Greg / Mr. Decorator Bryan Terrell Clark as Paul / Dr. Dermatologist Matthew Lawler as Todd / Tyler's Dad Josh Cooke as Ethan / Mr. Dolphin Shorts Hani Furstenberg as Dana / Mrs. Dolphin Shorts Kevin Mambo as Detective Roy John Charles Meyer as Joe / Movie Star 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 Emma Aurora Antun Castillo as Kaia / Darien Girl Merionne Toussaint as Stephen / Manager Hermann Brandt Hoffmann as Finn / Darien Boy Zani Jones Mbayise as Young Sara Lycott Judah Edwards as Young Gogo Brandon Gilpin as Keithley Constance Zaytoun as Dr. Norton Chase Dillon as Young Desmond Maria Cerdeiros as Gina / Movie Star's Girlfriend Richard A. Phillips as Young Keithley Cynthia Paola Guzman Tamares as Counselor