Nathan (Woody Harrelson) feels like the third wheel when Will returns from his vacation and resumes his friendship with Grace. Jack takes Elliot shopping for school clothes.
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Will's former bully from school is hired as a new attorney at his firm. Grace is upset that Karen's birthday gift to Nathan is better than hers.
Jacks talks Grace into being Elliot's date at his school prom. Karen pulls one too many practical jokes on Will.
When Will flubs his lines during an interview with a tv reporter, Jack talks him into attending his acting class. Grace moves in with Karen and quickly becomes accustomed to Karen's extravagant lifestyle. Eileen Brennan guest stars as Zandra.
Jack's boss has a crush on Will but Will thinks that she he interested in him for a modeling job. Karen and Nathan compare sex stories. Parkey Posey guest stars as Dorleen.
Grace is upset over Nathan's marriage proposal due to the fact that he popped the question while they were having sex.
Grace retreats to her bed after her break up with Nathan. Will tries to cheer her up.
Will and Grace become embroiled in politics when they each support a different city council candidate.
So that they can be together on Thanksgiving, Will, Grace, Karen and Jack travel together to meet their respective families. Guest stars Debbie Reynolds, Beau Bridges, Lainie Kazan, Blythe Danner, Nick Offerman (Megan Mullally's real life husband).
Part 2. So that they can be together on Thanksgiving, Will, Grace, Karen and Jack travel together to meet their respective families. Guest stars Debbie Reynolds, Beau Bridges, Lainie Kazan, Blythe Danner, Nick Offerman (Megan Mullally's real life husband).
Grace asks Karen for a loan to expand her company. Will and Jack join a gym.
Will is embarrassed by his ballet dancer boyfriend. Jack gets to decorate the window at Barney's. Guest star Parkey Posey.
Jack and Karen get into the horse business. Will and Grace attempt to get Will's father's girlfriend interested in someone else, but their plans backfire when they enlist their gay friend Larry to play the bait. Leslie Ann Warren guest stars.
While visiting Stan in prison, Grace meets a former high school friend, who is also serving time.
Grace takes Will along to her ex-fiancee's wedding so that she doesn't look destitute. Jack has a run- in with Elliot's mother. Guest star Rosie O'Donnell.
Jack tries to prove that his rival at the Gay Man's Chorus is straight. Karen asks Will to pose as her lover at a Valentine's Day party. Guest stars Matt Damon, Leslie Jordan.
Will and Grace search for a larger apartment. Jack films a documentary of Karen's life and meets her estranged mother. Suzanne Pleshette and Sandra Bernhard guest star.
Will and Grace miss their old apartment. Jack tries to reconcile Karen and her mother. Suzanne Pleshette guest stars.
An excited Will (Eric McCormack) presents his newly reconciled parents (guest stars Sydney Pollack and Blythe Danner) with a romantic cruise on their anniversary.
Will proudly displays a beloved garden gnome in their community garden. Jack is worried that his role as a heterosexual in a mattress commericial will stereotype him. Eileen Brennan guest stars.
Jack asks Will to accompany Elliot to a basketball tournament. Grace teaches a design class but her students seem to be more interested in celebrity gossip.
Grace gets too caught up in wedding fantasies when Will asks her to assist a friend with wedding plans. Jack becomes jealous when Will and Karen get chummy over a book that they are reading.
Will's laptop gets stolen and he meets a closet detective who takes an interest in him. Grace's neighbor Val opens a rival business. Molly Shannon and Michael Douglas guest star.
After Will (Eric McCormack) wins a portrait session at a charity auction, he takes Grace (Debra Messing) to pose for a notoriously eccentric celebrity photographer (Glenn Close).
Will asks Grace to be the mother of his baby. Jack auditions for a Broadway production.
Will and Grace decide to have a baby but encounter obstacles at the insemination lab. Jack wants to give up show business until he gets a dream message from his idol Cher. Cher and Rip Torn guest star.
Part 2. Will and Grace decide to have a baby but encounter obstacles at the insemination lab. Jack wants to give up show business until he gets a dream message from his idol Cher. Cher and Rip Torn guest star.