Guest Stars Conrad Ricamora as Oliver Hampton Tom Verica as Sam Keating Megan West as Lila Stangard Lenny Platt as Griffin O'Reilly Michael Gaston as Prosecutor Henry Williams Andrea Syglowski as Gina Sadowski Suzanne Savoy as Judge Kathy Powell Co Starring Aaron Benjamin Miller as Nerdy Intellectual Brian Gallagher as Maintenance Worker Allen Williamson as Drunk Dude Susan Wilder as Agnes Kaufman Kara Shoemaker as Bouncy Girl Alan Robert Pratt as Football Coach Robin Rieger as Reporter Olivia Luna as English Accent Girl Leah Lamarr as Mean Girl Kate Kearney-Patch as Linda Tanner Greg Wood as Arthur Kaufman Ellen Haun as Nervous Girl Dave Droxler as Detective Gill Leah Dowdy as Drunk Girl Ian Bedford as Campus Cop Timmy Reifsnyder as Monotone Quiet Guy John McKeever as Drunk Guy Joe Melendez as Lionel Bryant Jennifer Butler as WBQV Reporter Heather Soellner as Law Student Erica Lynne Marszalek as Law Student Uncredited Ashley James as Law Student