Guest Stars Pico Alexander as Josh Caleb Lowell as Tyler Kosha Patel as Sunita Sule Thelwell as Desmond Matthew Lawler as Todd / Tyler's Dad Matthew Risch as Greg / Mr. Decorator Bryan Terrell Clark as Paul / Dr. Dermatologist 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 Maury Ginsberg as Brett / Darien Dad Carter Burney as Young Edwin Emma Aurora Antun Castillo as Kaia / Darien Girl Hermann Brandt Hoffmann as Finn / Darien Boy Maria Cerdeiros as Gina / Movie Star's Girlfriend Ozzie Stewart as Grandmother Moïse Regis as Valet Ah'Mani Chance as Toddler Ederson Clot as Bartender Wesli Spencer as Homeless Man PrinceYarcadova Lewinson as Young Clive John Brugal as Trev Farrah Cine as Teacher Federico Parra as Young Dad Colin Kilkenny as Driver Johnny Sanchez as Clerk