Guest Stars Anthony Edwards as Alan Reed Gabriel Sloyer as Gabriel Calatrava Ben Rappaport as Billy McFarland India Ennenga as Julia Reed K.K. Moggie as Banker Tracy Pollan as Sherry Reed James Waterston as Squash Partner Co Starring Chris Cafero as David Morrison Jason Schuchman as Lavin Winslow Bright as Jenny Whitley Richie Herschenfeld as Richie Notar Niraj Arjan as Gavin Peterson Austin Ku as Michael Xufu Huang Lawrence Ballard as Jaffe Nicholas Calhoun as Reggie Walsh Esco Jouléy as Kehinde Ben Beckley as Male Suit Amelia Hammer Harris as Sade Migs Govea as Yakub Matthews Max Chernin as Hipster Mary Jo Mecca as Housekeeper Tony Neil Butler as Squash Attendant Justin Ariola as Security Guard Cristala Carter as Female Suit Michael Zegarski as Attendant Usama Siddiquee as Ron Wheaton Alex Bartner as Mark Nurit Monacelli as Lawyer Nikka Graff Lanzarone as Blaine Desi Domo as Alison Nick Ong as Admin Alex Weisman as Alan's Assistant