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Grace tries to keep the peace between her slovenly boyfriend and a resentful Will; Jack plans to meet his father for the first time.

Grace tries to keep the peace between her slovenly boyfriend and a resentful Will; Jack plans to meet his father for the first time.

Will and Grace (Eric McCormack, Debra Messing) resume their chummy relationship, leaving Nathan (guest star Woody Harrelson) feeling left out in the cold; Jack (Sean Hayes) and his son go school shopping.

Will suffers flashbacks when a childhood bully (Adam Goldberg) is hired by his law firm.

Jack coerces Grace into posing as his son Elliot's date to a school dance.

When Stan is arrested for tax evasion, Grace moves into Karen's apartment to help her worried friend.

Jack sets up unsuspecting Will on a date with a smitten supervisor; Grace and Nathan swap sexual histories.

Nathan's marriage proposal doesn't fulfill Grace's childhood fantasy, and she finds it dispiriting.

Will, Jack and Karen try and rouse a devastated and bed-ridden Grace after she loses her boyfriend, Nathan.

Will and Grace back different candidates for the upcoming mayoral election.

Will, Grace, Jack and Karen make a day of it as they head to Thanksgiving get-togethers at the houses of their respective families.

Will, Grace, Jack and Karen make a day of it as they head to Thanksgiving get-togethers at the houses of their respective families.

At the gym, Will sees a man (Patrick Breen) who seems familiar, while Jack tries to popularize a new saying.

Grace is hired to decorate the windows at Barney's; Will meets a ballet dancer and is too embarrassed to introduce his friends.

Grace schemes to hook up the mistress (Lesley Ann Warren) of Will's father with another man in order to break up the relationship.

After rediscovering a handsome high-school friend who's doing time, Grace dreams of their life together outside the Big House.

Grace reveals her ex-boyfriend's faults to his bride at the wedding rehearsal; Elliot's mother (Rosie O'Donnell) demands that Jack never see him again.

Jack uses Grace as bait to expose a rival (Matt Damon) as heterosexual in order to secure a spot in a gay men's chorus.

Will and Grace try to find more expansive digs despite the efforts of Sandra Bernhard; Jack stumbles across Karen's lowlife mother (guest star Suzanne Pleshette).

Moving into their new dream apartment makes Will and Grace homesick; Jack tries to reconcile Karen with her grifter mom (guest star Suzanne Pleshette).

Will presents his newly reconciled parents (Sydney Pollack, Blythe Danner) with a cruise for their anniversary, but their individual secrets ruin his hopes.

Will salvages a cherished garden gnome in the aftermath of his parent's divorce; Jack's afraid of being typecast as a straight man.

When Jack works instead of taking his son to a basketball tournament, he learns from Will that he missed his son's first kiss with a girl.

When the bride-to-be gets sick, Will persuades Grace to help plan the wedding for his visiting friends.

A detective (Michael Douglas) helps Will search for his stolen computer; a crazy neighbor (Molly Shannon) opens a business and prospers by stealing Grace's ideas.

Will takes Grace to have her picture taken after he wins a sitting with an eccentric celebrity photographer.

Will wants Grace to be the mother of his baby; Jack and Karen are inspired to pursue their own goals.

Will and Grace vacillate on artificial or natural means of conceiving a baby; Jack receives career advice from his show-business idol, Cher.

Will and Grace vacillate on artificial or natural means of conceiving a baby; Jack receives career advice from his show-business idol, Cher.

A dashing doctor (Harry Connick Jr.) on horseback rescues Grace; Karen debates cheating on her imprisoned husband with hot-blooded suitor Lionel (Rip Torn).

Stalking Kevin Bacon (guest starring as himself) pays off for Jack when he is hired as the actor's personal assistant; Will and Grace pursue parenthood. Harry Connick Jr. and Rip Torn also guest star.

Smitten with the handsome doctor (Harry Connick Jr.), Grace stalls for time to reconsider having a baby with Will.

Karen and Jack hatch a plan to end Will and Grace's ongoing feud by tricking them into attending the same child's birthday party.

Leo (guest star Harry Connick Jr.) drags Grace on a scary cycling trip in the autumn countryside. Jason Marsden also guest stars.

Will's aggressive new boss (Gene Wilder) orders him to fire his friend; Grace and Jack discover Karen is living out of her limousine.

Grace uses indecorous language when meeting Leo's parents; Jack's acting coach (Eileen Brennan) disparages his meager talent.

Grace begins to have cold feet as her relatives start arriving for her wedding, while Will tries to overcome his mixed emotions.

Will is uneasy about the whole idea of Grace marrying Leo (guest star Harry Connick Jr.). Debbie Reynolds and Katie Couric also guest star.

Will invites Karen to move in with him after she is kicked out of the Plaza Hotel; Elton John is an all-seeing arbiter of gay style.

Grace has only two tickets to "The Nutcracker" and cannot decide whether to take Will or Leo. Mary McDonough guest stars.

Jack convinces Will to join a gay soccer team; Karen is giddy in anticipation of her date with a handsome restaurateur (Andy Garcia).

Grace is puzzled by her new neighbor -- a bizarre bohemian woman.

Will and Jack coach Karen's cousin (Dan Futterman) on his new gay lifestyle, reminding Will of his own experience of coming out in 1986.

Karen's rival (Minnie Driver) attempts to manipulate Jack; Will and Grace revitalize their friendship with a night of board games.

Jack encounters his former babysitter (guest star Demi Moore) and lapses into childlike behavior. Rosanna Arquette and Leigh-Allyn Baker also guest star.

Will and Jack's transformation of Karen's cousin Barry is complete; Karen duels with Beverly during a silent auction for charity.

Jealous Will spots Barry (Dan Futterman) disappearing with Jack; Karen trades places with Rosario to woo a handsome handyman (Bruno Campos).

Will forms an anti-romance club with Karen and his boss (Gene Wilder).

Will attempts to surprise Grace for her birthday by sneaking Leo back from Africa; Jack and Karen take their mission to keep Leo's return secret too seriously.