Guest Stars Jane Seymour as Colleen Bash John Ratzenberger as Judge Elliott Reid James Remar as Cliff Kevin McKidd as Duke Albert Daughtery Diora Baird as Cindy Maloney Aaron Hendry as Ian Jack Plotnick as Tony Philbin Katrina Norman as Emilia Case Tyne Stecklein as Date #2 Melissa Molinaro as Date #1 Holly Hyman as Tia