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. Will is surprised at his reaction to making Senior Partner. Beverly Leslie discloses his secret to Karen. Jack owns half of a winning lottery ticket.

When Karen's has trouble dealing with a personal tragedy, Will, Grace, and Jack 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.

Jack's first day as a Lyft driver goes south when he rear-ends a wacky neighbor. An old friend decides he's in love with Will. Tim Bagley and Molly Shannon guest star.

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 TV.

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. Jennifer Lopez will pull double duty guest-starring as both herself and her "Shades of Blue" character, Det. Harlee Santos.

Will rekindles a relationship with his first love against Jack's advice. 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 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.