Will & Grace

Grace contemplates having an affair with a married man. Elsewhere, Jack begins new career as a host of his new talk show "Jack Talk." Will gets some advice from Malcolm and tries to hide from Karen the fact that Stan is alive.

Will makes it his own personal mission to emotionally heal Karen when he suspects that she is more upset about Stanley being alive than she's actually letting on. Surprisingly for him, he discovers a few areas where he needs some healing of his own. Meanwhile, Grace becomes the target of rage from gay men all over New York when her comments on Jack's (Sean Hayes) talk show are misconstrued during editing.

When Jack learns that Will never learned to swim, Jack insists that he teach Will how. Meanwhile, Karen sets Grace up on a blind date with one of Malcolms friends, but Grace can't stand him or his penchant for bad poetry during their seemingly never-ending nine-course dinner.

Karen is finally forced to come to terms with her feelings for her presumed-dead husband when Jack surprisingly tells her he thinks she belongs with Stanley, not Malcolm. Karen is adamant that she will never forgive Stan and wants nothing to do with him-until Malcolm informs her that Stan has given her to him without a fight. Meanwhile, the new, charitable Will begins doting on the elderly Clyde and invites him to the Tenth Anniversary Game Night Spectacular, much to Grace's (Debra Messing) dislike. He is worried that he will end up like Clyde one day-a lonely old gay, but it turns out that the old man and Will don't have as much in common as originally thought.

The day before Will's (Eric McCormack) charity auction and carnival, Jack meets and begins dating Baby Glenn, who is still riding his fifteen minutes of fame from when he got trapped in a hole for three days in the eighties. The two "celebrities" agree to be auctioned off for charity - Baby Glenn's fans spend over a thousand dollars, but Jack begins to question his own notoriety when no one bids on him. Meanwhile, Karen just can't force herself to break up with Malcolm, so to soften the blow she recruits Grace to be his date to the carnival. But Grace can't stand his weird quirks and clingy personality and finally makes Karen confront him.

While en route to London, Will and Grace spot Grace's ex-husband Leo on their flight. Will charms a pair of gay flight attendants, who also happen to be dating, so he can smuggle Grace into first class to talk to Leo. Back in New York, Jack tries to reunite Karen and Rosario, but this proves difficult when their stubbornness outweighs his good intentions. Also complicating matters is Karen's new manipulative maid Leni, who is not anxious to give up her comfortable new job.

When Jack decides on a whim to move, Will is excited at the thought of helping him look for a place. After becoming involved in a cause to save two gay penguins from being separated at the zoo, Will starts to think closely about his dear friendship with Jack and what it would mean if he no longer lived next door. Meanwhile, during an afternoon of shopping, Karen and Grace bump into pretentious socialite Beverly who invites the two ladies to attend his recently deceased wife's memorial celebration. When Grace decides to try on one of the dead wife's rare dresses before the ceremony, she experiences a wardrobe malfunction, which she must try to conceal.

Grace finds it impossible to put up with her mother Bobbi's (guest star Debbie Reynolds) constant nitpicking, so Jack takes it upon himself to help her because, according to him, no one knows how to be a good daughter better than a gay son. Jack subjects her to a barrage of Bobbi-esque insults until Grace finally learns what her mother really means underneath her harsh words. Meanwhile, Will's (Eric McCormack) first case at the Coalition for Justice is about tenants' rights, and the slumlord turns out to be none other than Karen.

While spending the holidays at Will's (Eric McCormack) mother Marilyn's (guest star Blythe Danner) house, Grace gets cozy with Will's brother and old flame Sam. Sam's adopted daughter finds a fan in Karen, who is intrigued by the little girl. Meanwhile, Jack helps Will's clearly gay ten-year-old nephew organize and perform a Christmas show, which Marilyn is thrilled about. Will is silently fuming, however, as Marilyn is much more tolerant of the young boy than she ever was of her own son.

The "Sound of Music Sing-Along" has come to town and no one is more excited than Grace. She plans for her and Will to attend the musical in character-like style by dressing up in costumes. However, her presumed-to-be fun night turns into a disaster when she ends up babysitting a group of children and Will accidentally goes to the wrong theater becoming further detained by James, a handsome man he meets. Meanwhile, Karen and Jack try to flee when she gets in trouble with the theater's manager, who blocks off the exits, trapping everyone inside and forcing them to plot their escape.

All of New York society attend Karen's birthday party, but Will, Grace and Jack embarrass themselves and get stuck in the bathroom with the birthday girl.

Grace is concerned and confused when Will so adamantly insists that she turn down her job offer from his former boss Margot, who has asked Grace to redecorate the law firm. When she takes the job after telling Will that she wouldn't, Grace learns some startling news that he has been hiding from her. Meanwhile, Jack discovers Karen's softer side when he finally sees what's inside the "forbidden room" at the Walker mansion.

Will and Grace dread a dinner date with married friends Rob and Ellen who likely called the meeting to announce Ellen is pregnant yet again, but when the couple reveals that they are separated and loving it, Grace gets depressed. She's quickly distracted however when Will's cop ex-boyfriend, Vince, approaches their table as their server. Ignoring Rob and Ellen's big news, Will and Grace discuss how Vince must have gone off the deep end and quit the force after splitting with Will, and Vince's request to switch table assignments seems to confirm their thoughts. Elsewhere, Jack decides he needs to spice up "JackTalk" by pulling an Oprah and helping his fan, Tommy Shields, come out of the closet. Jack and Karen setup a bowling alley meeting with Tommy when Karen is recruited to join a woman's league game as an emergency fill-in.

Will, Karen, and a star struck Grace travel to Los Angeles to support Jack as he accepts a HAPI award for Best Local Cable Gay Talk Show Host. Coincidently, Will runs into James while in LA, but to his surprise James is Canadian and in jeopardy of being deported. After spending a perfect weekend together, Will and James find that they don't have to say good-bye to each other again when Grace makes a special proposal.

Karen ignores Grace's plea for a low-key wedding and plans a huge affair, hiring Hall & Oates to perform "Maneater" at the ceremony.

A nervous but optimistic Grace decides it's finally time to tell Leo she is pregnant with his child, but when she finally works up enough courage to actually meet her ex-husband she receives some unexpected news. Meanwhile, Will is settling in comfortably with James until he reveals a side of himself unknown to Will. And as Jack attempts to document every moment of Grace's pregnancy for his talk show, Karen sulks alone, jealous over the good fortunes of her friends.

An ecstatic Jack coerces Will into coming out with him to a gay cowboy bar to meet his new boyfriend Travis. Will soon discovers that Travis is not as perfect as he seems and steps up to defend Jack's honor, which eventually leads to a raucous event - a bar fight.

After a large corporation takes over OutTV, Jack's talk show "JackTalk" is completely revamped. An immediate change comes when the new conservative owners hire Amber-Louise as "JackTalk's" new co-host. While Jack is deciding whether or not he'll stand up to his new bosses, Karen goes baby shopping. After seeing Grace so happy about her pregnancy, Karen decides she wants a baby of her own and offers to pay a make-up lady, Cricket, to carry one for her.

After losing his job as the host of "JackTalk," Jack vows never to return to acting. An unrelenting Karen, however, will not let Jack give up on his passion and decides to do whatever it takes to get Jack to an audition. Meanwhile, Grace accompanies Will to dinner at his parents' home, but a simple dinner soon turns into a showdown between Will and his father when his dad decides to give Grace's unborn child Will's cherished baby blanket.

Friends and family gather for the funeral of Will's father. During the reception everyone shares with Will fond last memories of his father, while Will's last memory of his father is not as pleasant. As he tries to come to terms with their last fight, Marilyn helps him realize the changes he must make in his life. Will's ex-boyfriend Vince also attends the funeral service. Meanwhile, Grace attempts to comfort the grieving younger members of the family and begins to doubt her ability to be a good mother.