Smitten with his new boyfriend Vince, Will puts his relationship to the test introducing him to the overly critical Grace for her approval. However, when Grace abruptly cuts the introduction short, Will is convinced of her disapproval of Vince and thus begins to question his own feelings. Meanwhile, Karen drops a bombshell on Jack, revealing that after her upcoming wedding their friendship will be forever changed, forcing him to begin casting calls for her replacement.
The show takes place in New York City and focuses on Will Truman, a gay man and lawyer, and his best friend Grace Adler, a Jewish woman who runs her own interior design firm.
Also featured are their friends Karen Walker, a rich socialite, and Jack McFarland, a struggling actor/singer/dancer who also has had brief careers as an acting teacher, back-up dancer, cater-waiter, talk-show host and student nurse.