Karen is unaware that her presumed-dead spouse---the never seen Stan---is actually alive. Her friends are reluctant to tell her because she's now involved with the enigmatic Malcolm (Alec Baldwin).

Stan's return rattles Karen, who feels lied to. Will offers solace---sort of. Meanwhile, Grace gets a rep as a homophobe on Jack's TV talk show, thanks to injudicious editing that she seeks to set straight in no uncertain terms.

Andy Richter guest stars as Grace's blind date, a cheery though clueless goof who's an old pal of Karen's tempestuous beau Malcolm. Elsewhere, Will takes swimming lessons---from Jack.

Richard Chamberlain appears as a sarcastic, reclusive buttinsky who figures in Grace's 10th annual trivia game. In other events, Stan reappears---sort of---in a very steamy steam room, where he's confronted by Malcolm, Karen's new love.

Jason Biggs plays Jack's new flame, a flighty egotist who had 15 minutes of TV fame as a preteen when he fell into a hole. Now he's a participant in Jack's corny carnival, where Grace is a reluctant date for Malcolm.

Harry Connick Jr. reappears as Leo, Grace's itinerant ex, whom she beguiles anew on a plane trip. Meanwhile, Karen's captivated by her new maid, a shrewd British matron (Millicent Martin) who takes an instant disliking to Jack.

Will is thrilled to help Jack look for another apartment, but after getting involved in an effort to help two gay penguins stay together at the zoo, he has second thoughts about his friend's move.

After another visit with her domineering mom, a frazzled Grace gets advice from Jack on how to deal with her. Meanwhile, on the first day of his new job, Will chases after a slumlord: Karen.

During a Christmas celebration at Marilyn Truman's house, Will, Grace, Jack and Karen debate about whether Will's "artistic" young nephew is gay. Also, Grace tries to comfort Will's brother (Steven Weber), whose divorce was just finalized.

Grace dresses like Maria for a sing-along screening of The Sound of Music, but Will, her Capt. Von Trapp, winds up at the wrong theater, where he meets a cute stranger (Taye Diggs). Meanwhile, the gang wonders how to solve a problem like Karen after she gets herself into trouble with theater management.