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.
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; Beverley Leslie discloses his secret to Karen; and Jack owns half of a winning lottery ticket.
Will (Eric McCormack), Grace (Debra Messing), Karen (Megan Mullally), and Jack (Sean Hayes) 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.