Special Guest Stars Jane Seymour as Madelyn Don Lemon as Himself Guest Stars Graham Rogers as Jude Jenna Lyng Adams as Darshani Melissa Tang as Margaret Chen Casey Thomas Brown as Lane Emily Osment as Theresa Ashleigh LaThrop as Breana Susan Sullivan as Eileen Newlander Adam William Zastrow as Marcus Rebekah Graf as Ricki David James Elliott as William Co Starring Kevin Stidham as Waiter Nick Toth as Dennis Maurice Webster as Workman Pamela Clay as First Wife