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The Third Wheel Gets The GraceNathan (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.
Past and PresentsWill'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.
Crouching Father, Hidden HusbandJacks talks Grace into being Elliot's date at his school prom. Karen pulls one too many practical jokes on Will.
Prison BluesWhen 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.
Loose Lips Sinks RelationshipsJack'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.
Rules of EngagementGrace is upset over Nathan's marriage proposal due to the fact that he popped the question while they were having sex.
Bed, Bath and BeyondGrace retreats to her bed after her break-up with Nathan. Will tries to cheer her up.
Star-Spangled BanterWill and Grace become embroiled in politics when they each support a different city council candidate.
Moveable FeastSo 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).
Stakin' Care of BusinessGrace asks Karen for a loan to expand her company. Will and Jack join a gym.
Jingle BallsWill is embarrassed by his ballet dancer boyfriend. Jack gets to decorate the window at Barney's. Guest star Parkey Posey.
Whoa, Nelly 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.
Grace in the HoleWhile visiting Stan in prison, Grace meets a former high school friend, who is also serving time.
Dyeing is Easy, Comedy is HardGrace 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.
A Chorus LieJack 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.
Someone Old, Someplace NewWill 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.
Something Borrowed, Something's Due (Part Two)Will and Grace miss their old apartment. Jack tries to reconcile Karen and her mother. Suzanne Pleshette guest stars.
Cheatin' Trouble BluesWill gives his reconciled parents a romantic cruise.
Went to a Garden PottyWill proudly displays a beloved garden gnome in their community garden. Jack is worried that his role as a heterosexual in a mattress commercial will stereotype him. Eileen Brennan guest stars.
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