Guest Stars Derek Mio as Wade Matthews Alan Ruck as Dean Bowman Anna Osceola as Robin Wylie Co Starring Zack Lively as Heath Adam Crosby as Pickle Steffany Huckaby as Beth Marisa Lauren as Brenda Henry Dittman as Sports Analyst Danièle Watts as Girl Ryan Rottman as Jess Uncredited Kristopher Hatfield as Jeremy