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 Stephanie March Brooke Guest Star James Lesure Elliot Guest Star Julie Hagerty Mrs. Kerkovich Guest Star Sally Ann Brooks Cousin Ann Guest Star Suanne Spoke Cousin Sherry Guest Star Christopher Darga Cousin Terry Guest Star Hugh B. Holub Reverend Guest Star Jamie Tarses Executive Producer Jonathan Groff Executive Producer Anthony Russo Executive Producer Joe Russo Executive Producer Josh Bycel Writer Leila Strachan Writer Rebecca Asher Director