Season 5

SeasonEpisodeAirdateEpisode TitleStory Line
05.019309/26/2002...And the Horse He Rode In OnA dashing doctor on horseback rescues Grace; Karen debates cheating on her imprisoned husband with hot-blooded suitor Lionel.
05.029410/03/2002Bacon and EggsJack stalks Kevin Bacon, who unwittingly hires him as his personal assistant, and then orders him to find his persistent pursuer. Grace gets a visit from a handsome doctor.
05.039510/10/2002The Kid Stays Out of the PictureA feud ensues between Will and Grace, whose second thoughts about having his baby are triggered by an infatuation with Leo.
05.049610/17/2002Humongous GrowthA plot hatched by Karen and Jack to reunite the estranged Will and Grace unfolds amid pandemonium at a child's birthday party.
05.059710/31/2002It's the Gay Pumpkin, Charlie BrownA bicycling adventure tests Will and Grace while up in the Catskills with Leo and his pal in a quest for Halloween pumpkins.
05.069811/07/2002Boardroom and a Parked PlaceMr. Stein, the long-absent senior partner of Will's firm, who shows up unexpectedly to reassume command. Meanwhile, Grace and Jack are shocked to discover that Karen is now living in her limo.
05.079911/14/2002The Needle and the Omelet's DoneGrace accompanies Leo to dinner with his parents. Meanwhile, Jack continues acting classes with Zandra; Will and Karen get Botox injections.
05.0810011/21/2002Marry Me a LittleAfter Grace impulsively accepts a marriage proposal from Leo, there seem to be a million roadblocks between her and an actual wedding (Part 1).
05.0910111/21/2002Marry Me a Little MoreAfter Grace impulsively accepts a marriage proposal from Leo, there seem to be a million roadblocks between her and an actual wedding (Part 2).
05.1010212/05/2002The Honeymoon's OverNeat-freak Will's new roomie is sloppy Karen, who moves in and makes herself cozy while Grace honeymoons; Meanwhile, Jack poses incognito out of fear that the "Gay Mafia" has it out for him.
05.1110312/12/2002All About Christmas EveChristmas Eve merriment turns sour for Will, riled by Grace's capricious requests that keep him from partying with Jack and Karen.
05.1210401/09/2003Field of QueensWhen Jack convinces Will to join him on a gay soccer team, Will's inept play leaves him warming the bench. Meanwhile, Grace is delighted that Karen is giddy in anticipation of her date with a handsome restaurant owner.
05.1310501/16/2003Fagmalion Part One: Gay It ForwardWill and Jack help Karen's cousin who recently decided to come out of the closet at age 35. Grace is puzzled over what to make of her strange bohemian neighbor when she moves into Leo's Brooklyn digs.
05.1410601/30/2003Fagmalion Part Two: Attack of the ClonesWill and Jack continue their campaign to adapt Karen's awkward cousin Barry to his new lifestyle. Meanwhile, Grace feels abandoned by Leo when he leaves to offer his medical services to the needy in Africa.
05.1510702/06/2003HomojoKaren is livid when Stan's new girlfriend befriends Jack. Meanwhile, Will and Grace try to re-connect their lagging friendship with a competitive night of board games with their friends.
05.1610802/13/2003Women and Children FirstGrace has a girl's night in Brooklyn with Karen, Rosario, Ellen and new neighbor Julie. Meanwhile, Jack reconnects with his childhood babysitter and falls back into childhood patterns, befuddling Will.
05.1710902/20/2003Fagmalion Part Three: Bye Bye BeardyA made-over Barry makes a big splash at a chic fund-raiser, where he also unwittingly arouses Will's romantic interest. Meanwhile, Karen duels with her flamboyant rival Beverley Leslie in a war of wills during a silent auction for charity.
05.1811003/13/2003Fagmalion Part Four: The Guy Who Loved MeThe pursuit of Barry pits Jack vs Will; lust for a hotel maintenance man consumes Karen, who poses as a maid to lure her prey.
05.1911104/03/2003Sex, Losers and VideotapeWill forms a gin-soaked anti-romance club with other lovelorn losers -- his cuckoo boss, Mr. Stein, and Karen. Desperate to learn the tricks of being seductive, Grace enrolls in Jack's acting class.
05.2011204/17/2003Leo UnwrappedWill attempts to surprise Grace for her birthday by sneaking Leo back from Africa.
05.2111304/24/2003Dolls and DollsKaren searches for a roommate and finds a high-maintenance individual who shares many of her eccentricities; Grace and Jack must intervene when Will uses painkillers as a crutch.
05.2211405/01/2003May Divorce Be With YouKaren hires a seemingly immature attorney to argue against Will in her divorce. Meanwhile, a wealthy client comes between Grace and Jack's friendship.
05.2311505/08/200323Stan's sudden death roils Karen, who confronts his mistress at his funeral, and demands that the will be read then and there.
05.2411605/15/200324Karen and the gang sets sail on her yacht to scatter Stanley's ashes in the Caribbean.