Will starts dating a 23 year-old. Jack is worried about getting old and decides to try something new. Grace and Karen solve their differences about work in an automatic shower.
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; Will is surprised to making Senior Partner; Beverley discloses his secret to Karen; Jack owns half of a winning lottery ticket.
Karen 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 as they pictured it.