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.

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 Jack visit Jack’s grandson, Skip, in Texas to watch him perform at his church’s talent show. But when Jack learns Skip plans on singing “Diamonds Are a Girl’s Best Friend,” he becomes afraid for his grandson’s safety. Karen tags along to check out the portion of the border wall she sponsored, only to discover that Beverley Leslie has claimed it as his own. Grace and Noah try to figure out if something is wrong in their relationship because their attempts to have sex have failed.

Will claims living with Grace is like Ricky living with Lucy; when Karen and Jack hear this, they each claim that they are the Lucy of the group; Grace, Karen and Jack each imagine themselves as Lucy, with Will as the Ricky to all of them.