Guest Stars Mark Derwin as George Juergens Molly Ringwald as Anne Juergens Matthew Levinson as John Joseph Levinson as John Jennifer Coolidge as Betty Anne Ramsay as Nora Renee Olstead as Madison Cooperstein Tricia O'Kelley as Camille Boykewich Tom Virtue as Reverend Stone Josie Bissett as Kathleen Bowman Kristin Bauer van Straten as Jack's Mom L. Scott Caldwell as Margaret Coby Ryan McLaughlin as Pimp Kathy Kinney as Bunny Ana Lucasey as Dillion Ben Weber as David Johnson Marielle Jaffe as Clementine Camille Winbush as Lauren Treacy DeVaughn Nixon as Omar Luke Zimmerman as Tom Bowman Michelle Marks as Tammy Allen Evangelista as Henry Miller Cian McGrath as Robie Logan McGrath as Robie Amy Rider as Alice Valko