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.
Will and Grace attempt to convince themselves it's okay to sleep with the same man; Jack and Karen get an annoying commercial jingle stuck in their heads.
Will and Grace's old friend Larry believes he's in love with Will; Val the clingy stalker is back, and she really wants Karen and Jack to be her friends.
Grace discovers she's dated three men from the same family. Meanwhile, Will and Karen develop their very own telenovela plot in the office while watching Karen's staff on her Home surveillance feed.
Grace brings Will for support when she goes home to celebrate her deceased mother's birthday; Jack's faith in love is crushed after a breakup; a secret in Karen's marriage is uncovered.
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.
