We pick up with Will (Eric McCormack), Grace (Debra Messing), Jack (Sean Hayes), and Karen (Megan Mullally) 11 years since we last saw them. Will and Grace both falter when their political beliefs are put to the test. Jack and Karen help Will and Grace hide their secret shame from each other, but the truth finally comes out.

Will (Eric McCormack) and Jack (Sean Hayes) try to date younger guys but find it challenging. Grace (Debra Messing) and Karen (Megan Mullally) experience a crisis that reveals Grace's true feelings about Karen.

Grace (Debra Messing) is shocked to find that the emergency contact called by her doctor's office is ex-husband Leo (special guest star Harry Connick, Jr.), not Will (Eric McCormack). Jack (Sean Hayes) takes on a new job he never expected to love. Karen (Megan Mullally) befriends a 12-year-old girl in the Bronx, despite her best efforts.

Jack (Sean Hayes) is stunned to learn that his estranged son, Elliot (guest star Michael Angarano) has a son of his own, Skip (guest star Jet Jurgensmeyer). Moreover, Skip needs the kind of help only Will (Eric McCormack) and Jack can provide. Grace (Debra Messing) and Karen (Megan Mullally) behave badly with the hot new guy at work.

Grace (Debra Messing) tries for her biggest job yet: decorating a string of boutique hotels for an obnoxious mogul (guest star Max Greenfield). Meanwhile, Will (Eric McCormack) is surprised at his reaction to making Senior Partner; Beverly Leslie (guest star Leslie Jordan) discloses his secret to Karen (Megan Mullally); and Jack (Sean Hayes) owns half of a winning lottery ticket.

When Karen's (Megan Mullally) has trouble dealing with a personal tragedy, Will (Eric McCormack), Grace (Debra Messing), and Jack's (Sean Hayes) try to intervene. Will and Grace's new business relationship begins to show signs of stress.