Will and Grace both falter when their political beliefs are put to the test; and Jack and Karen help them hide their secret shame from each other, but the truth finally comes out.

Will and Jack try to date younger guys but find it challenging. Grace and Karen experience a crisis that reveals Grace's true feelings about Karen.

Grace is shocked to find that the emergency contact called by her doctor's office is ex-husband Leo, not Will. Jack takes on a new job he never expected to love. Karen befriends a 12-year-old girl in the Bronx, despite her best efforts.

Jack is stunned to learn that his estranged son, Elliot has a son of his own, Skip. Moreover, Skip needs the kind of help only Will and Jack can provide. Grace and Karen behave badly with the hot new guy at work.

Grace tries for her biggest job yet: decorating a string of boutique hotels for an obnoxious mogul. Meanwhile, Will is surprised at his reaction to making Senior Partner; Beverly Leslie discloses his secret to Karen; and Jack owns half of a winning lottery ticket.

When Karen's has trouble dealing with a personal tragedy, Will, Grace, and Jack's try to intervene. Will and Grace's new business relationship begins to show signs of stress.

Will, Grace, Karen, and Jack wish they could have experienced Christmas in old New York City, but realize the past was not quite as romantic - or open to diversity - as they pictured it.

Will and Grace try to convince themselves they are okay with dating the same man; Jack and Karen get an annoying commercial jingle stuck in their heads and must seek medical attention.

Will and Grace's old friend Larry decides he's in love with Will. On Jack's first day as a Lyft driver, he hits his wacky neighbor Val. Karen steps in to bail out Jack, but then needs Jack to bail her out.

Will, Grace, Jack and Karen attend the wedding of Will's ex-boyfriend, Vince. While Grace tries to keep Will from making a scene, Jack learns that his wedding hookup has many strings attached.

Jack's intimacy issues are challenged by a closeted boyfriend; Will and Grace sell their new line of bedding on live television.

Grace is horrified to realize that she's dated three men from the same family; Will and Karen get on each other's nerves at the office until they bond over watching - and producing - their own little telenovela.

A baby shower makes Grace and Will question their life choices; Karen and Jack find a way to combine child labor with musical theater.

Against Jack's advice, Will rekindles a relationship with his first love; Grace reluctantly fights for Karen's civil rights when a bakery refuses to make a cake she wants.

Grace brings Will for support when she goes home to celebrate her deceased mother's birthday; Jack's faith in love is crushed after a breakup; a secret in Karen's marriage is uncovered.

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.