: Grace attempts to assert independence by moving into the apartment across the hall from Will, though they remain heavily codependent. Her dating life is a central focus, particularly her relationship with Josh and the season-ending introduction of Ben.

: Jack's storyline involves his sham marriage to Rosario to help her stay in the country, leading to them moving in together. He also explores diverse career paths and briefly falls for the leader of an organization for "ex-gays".

The second season of the American sitcom Will & Grace consists of 24 episodes that originally aired on NBC from September 21, 1999, to May 23, 2000. Often regarded by critics as one of the series' strongest years, this season balances the introduction of key narrative arcs with the solidified chemistry of the core ensemble.