Kaitlin Olson Mickey Actor Sofia Black-D'Elia Sabrina Actor Thomas Barbusca Chip Actor Jack Stanton Ben Actor Carla Jimenez Alba Actor Scott MacArthur Jimmy Actor Paul Ben-Victor Jerry Berlin Guest Star Jason Kravits Barry Guest Star Sam Pancake Oliver Fishburn Guest Star Avery Wada Dai Yamaguchi Guest Star Toshiya Agata Jun Yamaguchi Guest Star Thomas Crawford Club President Guest Star Kaylin Hayman Kid 1 Guest Star Kevin Reich Waiter Guest Star Corey Mendell Parker Golfer 1 Guest Star Jeff Witzke Golfer 2 Guest Star John Chernin Executive Producer Dave Chernin Executive Producer Nick Frenkel Executive Producer Oliver Obst Executive Producer Randall Einhorn Executive Producer