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


No. in
No. in
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 an 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 at Karen's.
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 back 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 to learn 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
Grace hits the roof when her matchmaking mom 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
With 90 percent 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
After Will closes his 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 an adult film.
29 7 Homo for the Holidays Alex Herschlag James Burrows November 25, 1999
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
Grace looks to Will for 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
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
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
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 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
36 14 Acting Out David Kohan & Max Mutchnick James Burrows February 22, 2000
37 15 Advise and Resent Jon Kinnally & Tracy Poust James Burrows February 29, 2000
38 16 Hey La, Hey La, My Ex-Boyfriend's Back Jeff Greenstein James Burrows March 14, 2000
39 17 The Hospital Show Adam Barr James Burrows March 28, 2000
40 18 Sweet and Sour Charity Gail Lerner James Burrows April 4, 2000
41 19 An Affair to Forget Alex HerschlagLaura Kightlinger James Burrows April 18, 2000
42 20 Girls, Interrupted Jon Kinnally, Tracy Poust & Jhoni Marchinko James Burrows May 2, 2000
43 21 There But for the Grace of Grace Michelle Bochner James Burrows May 9, 2000
44 22 My Best Friend's Tush Ellen Idelson & Rob Lotterstein James Burrows May 16, 2000
45 23 Ben? Her? David Kohan & Max Mutchnick James Burrows May 23, 2000[


  • Last season to feature recurring character Harlin Polk.

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