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Where there's a Will there's a Grace.
Will Truman and Grace Adler are best friends living in New York, and when Grace's engagement falls apart, she moves in with Will. Together, along with their friends, they go through the trials of dating, sex, relationships and their careers, butting heads at times but ultimately supporting one another while exchanging plenty of witty banter along the way.
Grace contemplates having an affair with a married man. Elsewhere, Jack begins new career as a host of his new talk show "Jack Talk." Will gets some advice from Malcolm and tries to hide from Karen the fact that Stan is alive.
Karen feels rattled by Stan's return and Will steps in to help her. Meanwhile Grace is labeled homophobic after her comments on Jack's talk show are misconstrued by gay men from all over New York.
When Jack learns that Will never learned how to swim, Jack insists that he teach Will how. Meanwhile, Karen sets Grace up on a blind date with one of Malcolm's friends.
Karen is finally forced to come to terms with her feelings for her presumed-dead husband when Jack surprisingly tells her he thinks she belongs with Stanley, not Malcolm.
The day before Will's charity auction and carnival, Jack meets and begins dating Baby Glenn, who is still riding his fifteen minutes of fame from when he got trapped in a hole for three days in the eighties.
While en route to London, Will and Grace spot Grace's ex-husband Leo on their flight. Will charms a pair of gay flight attendants, who also happen to be dating, so he can smuggle Grace into first class to talk to Leo.
When Jack decides on a whim to move, Will is excited at the thought of helping him look for a place. While attending Beverley's wife's memorial "celebration," Karen and Grace experience a wardrobe malfunction, which they must try to conceal.
Grace finds it impossible to put up with her mother Bobbi's constant nitpicking, so Jack takes it upon himself to help her because, according to him, no one knows how to be a good daughter better than a gay son.
While spending the holidays at Will's mother Marilyn's house, Grace gets cozy with Will's brother and old flame Sam. Sam's adopted daughter finds a fan in Karen, who is intrigued by the little girl.
The "Sound of Music Sing-Along" has come to town and no one is more excited than Grace. She plans for her and Will to attend the musical in character-like style by dressing up in costumes.
Karen celebrates her birthday with some of New York's crème de la crème, but the festivities turn sour when she ends up crammed in the bathroom with Grace, Will and Jack, who have all embarrassed themselves at the party.
Grace is concerned and confused when Will so adamantly insists that she turn down her job offer from his former boss Margot, who has asked Grace to redecorate the law firm.
Will and Grace dread a dinner date with married friends Rob and Ellen who likely called the meeting to announce Ellen is pregnant yet again, but when the couple reveals that they are separated and loving it, Grace gets depressed.
Will, Karen, and a star struck Grace travel to Los Angeles to support Jack as he accepts a HAPI award for Best Local Cable Gay Talk Show Host. Coincidently, Will runs into James while in LA, but to his surprise James is Canadian and in jeopardy of being deported.
The big day has finally arrived - Grace and James are getting ready for their green card wedding. To Grace's dismay, Karen takes it upon herself to ignore her wish for a low-key wedding ceremony and decides to arrange including hiring Hall & Oates.
A nervous but optimistic Grace decides it's finally time to tell Leo she is pregnant with his child, but when she finally works up enough courage to actually meet her ex-husband she receives some unexpected news.
An ecstatic Jack coerces Will into coming out with him to a gay cowboy bar to meet his new boyfriend Travis. Will soon discovers that Travis is not as perfect as he seems and steps up to defend Jack's honor, which eventually leads to a bar fight.
After a large corporation takes over OutTV, Jack's talk show "JackTalk" is completely revamped. An immediate change comes when the new conservative owners hire Amber-Louise as "JackTalk's" new co-host.
After losing his job as the host of "JackTalk," Jack vows never to return to acting. An unrelenting Karen, however, will not let Jack give up on his passion and decides to do whatever it takes to get Jack to an audition.
Friends and family gather for the funeral of Will's father. At the reception everyone shares with Will fond last memories of his father, while Will's last memory of his father is not as pleasant. Marilyn helps him realize the changes needed in his life.
