Het seizoen 1 van Jack & Jill werd uitgezonden op The WB van dimanche 26 septembre 1999 tot dimanche 19 mars 2000. Het bestaat uit 19 afleveringen, de eerste heet "These Are the Days (a.k.a Pilot)" en de laatste "Starstruck".
JACK & JILL was a romantic drama about life and loves of young people in New York, Jacqueline "Jack" Barrett and David "Jill" Jillefsky, and their friends, Mikey Russo, Barto Zane, Elisa Cronkite and Audrey Hriffin. The show follows their lifes after college, as they are trying to reach over to the adult life, forgetting about their childhood, exploring their sexuality, and finding the difference between a fairy tale and real life.