Grace brings Will for support when she goes home to celebrate her deceased mother's birthday. Jack's faith in love is crushed after breaking up with Drew and uncovering a secret in Karen's marriage.

Grace's father and Will's mother end up making a surprising and upsetting connection. Jack rebounds from his breakup with a new love. Karen must decide between her husband and her lover.

Will, Grace and Jack are upset when they discover they’ve been too preoccupied with the changes in their own lives: Will teaching law at Columbia, Grace running for president of the New York Interior Designers Society and Jack’s new relationship with Estefan to even notice Karen has not been seen in days – ever since her husband found out about her affair with Malcolm.

Malcolm enlists Grace to help him win back Karen's affections. Will's flirtation at work lands him in an ethical dilemma. Jack's passion for performing is reignited by a chance encounter with Zusanna, the sister of his former acting teacher.