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The second season of Will & Grace premiered on September 21, 1999 and concluded on May 13, 2000. It consists of 24 episodes.

Main Cast

Recurring Cast

Guest stars

Episodes

No. in
series
No. in
season
Title Writer Director Original air date
23 1 Guess Who's Not Coming to Dinner David Kohan & Max Mutchnick James Burrows September 21, 1999
Ep 02 01
After a newly independent Grace moves into a new apartment across the hall, she decides to throw a dinner party all by herself. Will isn't invited, but he has a date. Meanwhile, to solve problems with the INS, Jack moves in with his new bride Rosario in the maid's quarters in Karen's mansion.
24 2 Election Adam Barr James Burrows September 28, 1999
Ep 02 02-1
When Grace feels that Will is abusing his power as president of the tenant's association, she runs against him. Karen tries to buy Jack's forgiveness when she lets his beloved bird, Guapo, fly out the window.
25 3 Das Boob Jhoni Marchinko James Burrows November 2, 1999
Ep 02 03
A deceiving, but flattering, newspaper photo makes Grace look more "endowed" than she really is and gains her the attention of a former high school heartthrob who was never one to keep abreast of her before. Jack is destroyed when he learns that Will had a fling with Walter, Jack's ex-boyfriend.
26 4 Whose Mom Is It, Anyway? Alex Herschlag James Burrows November 9, 1999
Will&GraceTitle
Grace hits the roof when her matchmaking mom, Bobbi, visits with yet another man in tow: one of Grace's childhood friends. At first Grace is infuriated by her mom's matchmaking, but her anger soon turns to disappointment when he turns out to be a perfect match...for Will. Meanwhile, Jack and Rosario meet with an INS agent who's well acquainted with Jack's past.
27 5 Polk Defeats Truman Jeff Greenstein James Burrows November 16, 1999
Will&GraceTitle
With 90% of his practice now devoted to the wealthy Harlin Polk, Will dismisses all of his smaller clients, who believed in him before he became a success. But when Harlin's deal falls through, Will finds himself out of work. Meanwhile, Karen's husband Stan puts his foot down and tells her to quit her wild spending, and Grace steps in to help her friend master the art of living within a budget by taking her outlet shopping.
28 6 To Serve and Disinfect Katie Palmer James Burrows November 23, 1999
Will&GraceTitle
After Will closes his law firm office, Jack challenges him to become a cater-waiter on his staff; Meanwhile, Grace finds out a dirty secret about Karen when she catches her at work....in an adult film.
29 7 Homo for the Holidays Alex Herschlag James Burrows November 25, 1999
Will&GraceTitle
Will invites Jack's mother to Thanksgiving dinner as a surprise, only to discover that Mrs. McFarland doesn't know her son is gay; instead, Jack has claimed that he and Grace used to date. Will and Grace encourage Jack to tell the truth, while Karen is more upset by the fact that he chose Grace to be his imaginary girlfriend instead of her. When Jack finally works up the courage to confess, his mother reveals a secret of her own
30 8 Terms of Employment David Kohan & Max Mutchnick James Burrows November 30, 1999
Will&GraceTitle
Grace looks to Will for legal representation when a hotshot lawyer doesn't pay her for a consulting assignment, but he ends up making Will a job offer. Meanwhile, Jack and Karen turn a training film set into an adult entertainment experience.
31 9 I Never Promised You An Olive Garden Jon Kinnally & Tracy Poust James Burrows December 14, 1999
Will&GraceTitle
Tired of Rob and Ellen's low-rent taste in dining, Will and Grace start hanging with a pair of hip downtowners they meet at a sushi joint. But as the new pals paint the town, Rob and Ellen see red when they catch their best friends lying to avoid plans to dine at their favorite eatery: a coupon-crazy Italian chain in Secaucus. Meanwhile, Jack's inner child gets a little pick-me-up when he joins Karen at a PTA meeting at her kid's school.
32 10

Tea and a Total Lack of Sympathy

Jon Kinnally & Tracy Poust

James Burrows January 11, 2000
Will&GraceTitle
When Ben tells Will that he has until Friday to find a new client or lose his job, Will kisses up to Karen to appease his new boss. Jack and Grace try to get on their favorite television show and then get into hot water over an antique teapot.
33 11 Seeds of Discontent Jhoni Marchinko James Burrows January 25, 2000
Will&GraceTitle
When Will's best friend from high school asks Will to be the father of her baby, a jealous Grace tries to thwart her baby-making plans.
34 12 He's Come Undone Adam Barr James Burrows February 8, 2000
Will&GraceTitle
Will is having a recurring dreams in Grace enters his room and night and has sex with him, leaving him uncomfortable and confused. At Jack's suggestion, he seeks therapy in order to find clarity. However, the therapist, Dr. Loranger is disinterested in Will and instead attempts to pursue a romantic relationship with Grace, even using his sessions with Will to learn how to seduce her.
35 13 Oh Dad, Poor Dad, He's Kept Me in the Closet and I'm So Sad Katie Palmer James Burrows February 15, 2000
Will&GraceTitle
Will's ideal relationship with his loving father sours when his dad prepares to accept an award at his company's dinner banquet but tries to dissuade his son from attending because he's told everyone that Will is married to Grace. Meanwhile, Karen's private detective finds Jack's biological father.
36 14 Acting Out David Kohan & Max Mutchnick James Burrows February 22, 2000
Will&GraceTitle
Will and Jack appear on "Today" to protest NBC for yanking a gay kiss from a sitcom episode. Meanwhile, Grace seeks Karen's advice on dumping a weirdo beau.
37 15 Advise and Resent Jon Kinnally & Tracy Poust James Burrows February 29, 2000
Will&GraceTitle
When Will is set up on a blind date by his boss, he has internal debates on whether or not to go. Of course, Jack gives Will advice on how to be a good blind date. Meanwhile, Grace continues to struggle with her wimpy boyfriend Josh as Karen doles out some typically un-wanted advice.
38 16 Hey La, Hey La, My Ex-Boyfriend's Back Jeff Greenstein James Burrows March 14, 2000
Will&GraceTitle
Will thinks that he has another chance with Michael, his old boyfriend and Grace's new client. Meanwhile, Karen tries taking her "career" more seriously and asks Grace for greater responsibilities.
39 17 The Hospital Show Adam Barr James Burrows March 28, 2000
Will&GraceTitle
While on a blind date, Will finds out that Karen's husband Stan has had a heart attack and rushes to the hospital to be with the gang. Will, Jack, Grace, and Rosario all speculate on who Karen will turn to for her inevitable emotional breakdown. After all, who will pay the bills if Stan dies?
40 18 Sweet and Sour Charity Gail Lerner James Burrows April 4, 2000
Will&GraceTitle
After winning concert tickets from a radio contest, Grace vows to get more involved and she volunteers herself and Will to help out at the community center. Unfortunately, her charitable work conflicts with the concert. Meanwhile, while collecting clothes to give to the mission, Jack donates a pair of Karen's most-prized shoes.
41 19 An Affair to Forget Alex HerschlagLaura Kightlinger James Burrows April 18, 2000
Will&GraceTitle
When Rob and Ellen ask Will and Grace to be the best man and maid of honor at their wedding, Grace's sexy past with the groom is exposed when Ellen learns at her bachelorette party that Grace once slept with Rob. Meanwhile, Jack is confused by his reaction to the entertainment at Rob's bachelor party.
42 20 Girls, Interrupted Jon Kinnally, Tracy Poust & Jhoni Marchinko James Burrows May 2, 2000
Will&GraceTitle
Despite their history, Grace spends a fun evening with Val only to have Will suspect her of stealing. Meanwhile Jack becomes attracted to the leader of Welcome Home, an organization for gays who have converted to going straight, so he acts straight to woo the man.
43 21 There But for the Grace of Grace Michelle Bochner James Burrows May 9, 2000
Will&GraceTitle
It's a scary glimpse into the future for Will and Grace when they visit their curmudgeonly retired college professor only to discover that he is a bitter old man that has a "Grace" of his own. Meanwhile, Karen must confront her most mortal enemy, the kitchen, when Stan requests a home-cooked meal for his birthday, and she looks to Jack and Ben to come to her rescue.
44 22 My Best Friend's Tush Ellen Idelson & Rob Lotterstein James Burrows May 16, 2000
Will&GraceTitle
Grace is thrilled when, thanks to Karen's social connections, she gets the chance to land a prestigious client for her interior-decorating firm. The only problem? She must compete with international design goddess Helena Barnes. To help boost Grace's confidence, Karen assumes the alias of "Anastasia Beaverhausen" to dig up dirt on the socialite. Meanwhile, Jack tries marketing an odd invention: a tush pad for riding the New York City subway.
45 23 Ben? Her? David Kohan & Max Mutchnick James Burrows May 23, 2000[
Will&GraceTitle
To help make peace between Grace and Ben, Will has them both over to dinner, only to have their relationship go beyond friendship. But then Will finds out that Ben is dating someone else. Meanwhile Jack catches Rosario in a clinch with a lover and learns that she wants a divorce.

Notes

  • Last season to feature recurring character Harlin Polk.

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