Jack & Jill (1999)

This WB drama is named after two of the six main characters, each with a name rather suggesting the other gender: Jaqueline 'Jack' 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.