"Jack" moves to New York, and inadvertently steals the boyfriend office mate's "Jill", who is thinking of taking the next step with her girlfriend. Jack and Jill, romantically involved, face major obstacles in their current relationships.

This WB drama is named after two of the six main characters, each with a name rather suggesting the other gender: Jaqueline 'Jack' Barrett and David 'Jill' Jillefski, who gradually realize they were in love at first sight. The other main characters are brilliant but insecure med student Barto; philosopher-barman Mikey, a natural womanizer who cultivates immaturity and disarming charm; Broadway-actress/dancer Audrey, who becomes Barto's girl; and Elisa Cronkite, Jack's colleague at the TV station.—KGF Vissers