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 Brian Austin Green Chris Guest Star Stephen Guarino Derrick Guest Star Nate Smith Eric Guest Star Larry Wilmore Mr. Forristal Guest Star Daniel Rhyder Pitchy Pete Guest Star Michael Rubenstone Hugh Guest Star Richard John Reliford Jeff Guest Star John C. Moskoff Uncle Jerry Guest Star Jamie Tarses Executive Producer Jonathan Groff Executive Producer Anthony Russo Executive Producer Joe Russo Executive Producer Josh Bycel Writer Leila Strachan Writer Rob Greenberg Director