Season 2

SeasonEpisodeAirdateEpisode TitleStory Line
02.012309/21/1999Guess Who's Not Coming To DinnerGrace moves across the hall and throws a dinner party without Will. Jack moves in with Rosario and Karen.
02.022409/28/1999ElectionWill and Grace compete for tenant-board president. Karen loses Guapo.
02.032512/14/1999I Never Promised You an Olive GardenFriends become jealous when Will and Grace begin hanging out with a hip young couple.
02.042611/02/1999Das BoobGrace tries to live up to her new "dimensions" when a deceiving, but flattering, picture of her appears in a newspaper.
02.052711/09/1999Whose Mom Is It, Anyway?Grace's mom shows Will a little too much attention for her jealous daughter's taste. Jack and Rosario meet with an INS agent.
02.062811/16/1999Polk Defeats TrumanWill lets his ego get the better of him when he dismisses the clients who believed in him before he became a success. Grace takes Karen outlet shopping.
02.072911/23/1999To Serve and DisinfectJack challenges unemployed Will to become a waiter on his staff; Grace finds out a dirty secret about Karen.
02.083011/25/1999Homo For The HolidaysWill and Grace invite Jack's mother to Thanksgiving dinner and learn that she is unaware that her son is gay.
02.093111/30/1999Terms of EmploymentGrace looks to Will for representation when a lawyer doesn't pay her for a consulting assignment. Meanwhile, Karen helps Jack on the set of a sexual harassment training video.
02.103201/11/2000Tea and a Total Lack of SympathyWill kisses up to Karen to appease his new boss; Jack and Grace get into hot water over an antique teapot.
02.113301/25/2000Seeds of DiscontentWhen an old school chum asks Will to father her child, a jealous Grace tries to thwart her baby-making plans.
02.123402/08/2000He's Come UndoneWill's sexy dreams about Grace land him in therapy and send her on a couch trip with his hunky shrink. Meanwhile, Jack and Karen clash over her treatment of Rosario.
02.133502/15/2000Oh Dad, Poor Dad, He's Kept Me In The Closet and I'm So SadWill's father tells his colleagues that his son and Grace are married; Jack prepares to meet his biological father.
02.143602/22/2000Acting OutWill and Jack go straight to the network when a scheduled kiss between two gay TV characters doesn't happen. Grace seeks Karen's advice on dating.
02.153702/29/2000Advise and ResentWill gets advice from Jack on how to handle a blind date arranged by his boss. Meanwhile, Grace once again seeks Karen's advice about Josh.
02.163803/07/2000Hey La, Hey La, My Ex-Boyfriend's BackWill has designs on Grace's newest interior-decorating client--his ex-boyfriend; Karen tries taking her "career" more seriously.
02.173903/28/2000The Hospital ShowAfter Karen's husband suffers a heart attack, there is speculation on whom she will turn to for support.
02.184004/04/2000Sweet (and Sour) CharityAs the gang plunges into charity work, Will and Grace direct a kids' play, while Jack infuriates Karen by giving away her favorite pair of pumps.
02.194104/18/2000An Affair To ForgetEllen learns at her bachelorette party that Grace once slept with her fiance Rob.
02.204205/02/2000Girls, InterruptedGrace suspects Val may have stolen her music box; Jack plays straight to woo a heterosexual convert.
02.214305/09/2000There But for the Grace of GraceWill and Grace are alarmed when the friendship of two bickering oldsters mirrors their own; Ben impresses Jack and Karen with his hidden talents.
02.224405/16/2000My Best Friend's TushGrace finds out that one of Karen's friends is her competition for an important interior design job. Meanwhile, Jack tries marketing an odd invention.
02.234505/23/2000Ben? Her?Will discovers that Grace is dating his boss; Rosario requests a divorce from Jack so that she can be with Karen's Gardener.