Guest Stars David Magidoff as Teddy Reed Jamie Chung as Molly Park Katy Sullivan as Esther Gizel Jimenez as Tess Alton Fitzgerald White as Morris Cooper Co Starring Andrew Fama as Scott Oscar Wahlberg as Zach Skyler Wright as Chloe Benjamin Breault as Adam Kallie Tabor as Winnie Luke Crory as Boyfriend Mitch Fortier as Coach Mitch Michael Carroll as Referee Devlin Carroll as Jeremy Patrick Vincent Curran as Bartender