Will, Grace, Jack and Karen attend the wedding of Will's ex-boyfriend, Vince. Karen steps in to bail out Jack, but then needs Jack to bail her out. On Jack's first day as a Lyft driver, he hits his wacky neighbor Val. Will and Grace's old friend Larry decides he's in love with Will. 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. When Karen has trouble dealing with a personal tragedy, Will, Grace, and Jack try to intervene.

Meanwhile, Will is surprised at his reaction to making Senior Partner Beverley Leslie giving his secret to Karen and Jack owns half of a winning lottery ticket. 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. Furthermore, Skip needs the kind of help only Will and Jack can provide. Jack is stunned to learn that his estranged son, Elliot has a son of his own, Skip. Karen befriends a 12-year-old girl in the Bronx, despite her best efforts. Jack takes on a new job he never expected to love. 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. Will and Jack try to date younger guys but find it challenging. 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.

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