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