After running into a light post, Grace is rescued by a handsome Jewish doctor on a horse (Harry Connick Jr.). Karen is wooed by a suave suitor (Rip Torn).
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Jack is hired as Kevin Bacon's personal assistant but Bacon doesn't realize that Jack has been stalking him. Grace gets a visit from Dr. Leo (Harry Connick Jr.).
Infatuated by her handsome doctor, Grace has second thoughts about conceiving a child with Will.
Will and Grace continue to feud over their planned parenthood. Jack and Karen trick them into attending a child's birthday party.
A bicycling adventure tests Will and Grace while up in the Catskills with Leo and his pal in a quest for Halloween pumpkins.
A senior partner in Will's firm (Gene Wilder) assumes command. Karen and Jack are shocked to discover that Karen is living in her limo.
Karen talks Will into getting a Botox injection. Jack has another run-in with his acting teacher Zandra (Eileen Brennan). Grace makes a fool of herself in front of Leo's parents (Tom Skerritt and Judith Ivey).
Grace accepts Leo's marriage proposal but numerous conflicts cause Grace to question her decision.
Will is upset over Grace's marriage to Leo.
Will reluctantly lets Karen move in with him. Jack goes incognito to escape the gay Mafia.
On Christmas Eve, Grace (Debra Messing) is torn when she has only two tickets to 'The Nutcracker' musical and can't take both her best friend Will (Eric McCormack) and new husband Leo
Will and Jack join a gay soccer team. Karen falls for a handsome restaurant owner (Andy Garcia) but is depressed when he doesn't return her call.
Will and Jack attempt to transform Karen's geeky, in-the-closet cousin (Dan Futterman). Grace meets her new neighbor, a far-out masseuse (Roseanna Arquette).
Will and Jack continue their efforts to transform Barry (Dan Futterman). Grace is upset when Leo leaves on a three-week mission to Africa.
Will and Grace fear that their friendship has lost its spark. Karen is jealous when Jack befriends her British rival, Lorraine Finster (Minnie Driver).
Demi Moore plays Jack's former baby-sitter who comes back into his life. Grace has a girls-night-out with Rosario, Karen and Julie.
Will develops feelings for the newly transformed Barry (Dan Futterman). Karen and Beverly Leslie (Leslie Jordan) attend a silent charity auction.
Will and Jack force Barry to choose between them. Karen dons Rosario's maid uniform in order to attract a handsome maintenance man.
Grace enrolls in Jack's acting class in order to make a sexy video for Leo. Will, Karen and Mr. Stein (Gene Wilder) form an anti-romance club.
Will attempts to surprise Grace for her birthday by sneaking Leo back from Africa.
Madonna plays Liz, Karen's crazy new roommate. Jack and Grace are afraid that Will might be addicted to painkillers.
Karen hires a young hot-shot lawyer (MaCauley Culkin) for her divorce case when she finds that Will is acting as Stan's attorney.
Stan dies and Karen and Lorraine (Minnie Driver) battle for his estate. Leo asks Grace to accompany him to Gautemala.
Karen and the gang set sail on her yacht to scatter Stan's ashes. Karen is not too happy to find that Lorraine is a stow-away. Grace is worried about Leo's foxy traveling companion (Nicolette Sheridan). Will and Jack get drunk and pass out together.