Jack Sheridan, a cheeky charmer, was Prue Halliwell's unorthodox rival in the arts trade but gets employed in Rex Buckland's Auction House and becomes her partner, clearly into her but finding her extremely hard to get, yet succeeds becoming her boyfriend for a short period of time in season 2. He and his twin brother, Jeff, play a game whenever they find interest in a girl, checking out the female merchandize . He and Prue date separate for good when she quits her job at Bucklands.