Guest Stars Lynsey Bartilson as Megan Damien Leake as Principal Alburton Noah Segan as Robby Bennett Harry S. Murphy as Mr. Bennett Christopher Miranda as Tommy Billy Gallo as Stitch Krystin Moore as Julie Bert L. Cook as Delivery Man Brad Parker as Refreshment Guy Jessica Smith as Jenny Matt Zusser as Donald Uncredited Meghan Markle as Student Sitting on Stage