Guest Stars Anna Chlumsky as Josie Lee Tergesen as Clint Constance Zimmer as Hallie Julie Hagerty as Liv Colton James as Marshall Annabelle Gurwitch as Manday Co Starring Gillian Zinser as Beatnik Sexpot Jordan Hayes as 16-Year-Old Boxer Paul Urcioli as Ronni Steve Greenstein as Father No. 2 Greg McFadden as Jack David Lavine as Meek Man Kari Swenson Riely as Conservative Woman Eric Saiet as Mr. Roberts Susie Stewart Rubio as Skyler Gayle Samuels as Fortysomething Woman Juan Luis Acevedo as Father No. 1 Brian McCormack as Bully's Dad Angelo Massagli as Bully Gideon Banner as Liberal Man John R. Tigonis as Hector Natalie Douglas as Mother No. 1 Leona Cyphers as Mother No. 2