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 Lance Briggs Himself Guest Star Bergen Williams Dragga Guest Star Matt Walsh Duckie Blenkinship Guest Star Scott Prendergast Green Monkey Guest Star Seth Morris Scotty Guest Star Billy Merritt Umpire 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 Jackie Clarke Writer Gil Ozeri Writer Gail Lerner Director