Eliza Coupe Jane Actor Elisha Cuthbert Alex Actor Zachary Knighton Dave Actor Adam Pally Max Actor Damon Wayans Jr. Brad Actor Casey Wilson Penny Actor Meagen Fay Barbara Guest Star Cade Dundish Boy Guest Star Heather Fox Ellen Guest Star Bre Blair Kim Guest Star Clint Culp Paul Guest Star Gina Rodriguez Rita Guest Star Isabella Crovetti Young Alex Guest Star Daisy Stoneman Young Jane Guest Star Jamie Tarses Executive Producer Jonathan Groff Executive Producer Anthony Russo Executive Producer Joe Russo Executive Producer Prentice Penny Writer Lee Shallat Chemel Director