| Season | Episode | Airdate | Episode Title | Story Line |
| 02.01 | 23 | 09/21/1999 | Guess Who's Not Coming To Dinner | Grace moves across the hall and throws a dinner party without Will. Jack moves in with Rosario and Karen. |
| 02.02 | 24 | 09/28/1999 | Election | Will and Grace compete for tenant-board president. Karen loses Guapo. |
| 02.03 | 25 | 12/14/1999 | I Never Promised You an Olive Garden | Friends become jealous when Will and Grace begin hanging out with a hip young couple. |
| 02.04 | 26 | 11/02/1999 | Das Boob | Grace tries to live up to her new "dimensions" when a deceiving, but flattering, picture of her appears in a newspaper. |
| 02.05 | 27 | 11/09/1999 | Whose 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. |
| 02.06 | 28 | 11/16/1999 | Polk Defeats Truman | Will 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. |
| 02.07 | 29 | 11/23/1999 | To Serve and Disinfect | Jack challenges unemployed Will to become a waiter on his staff; Grace finds out a dirty secret about Karen. |
| 02.08 | 30 | 11/25/1999 | Homo For The Holidays | Will and Grace invite Jack's mother to Thanksgiving dinner and learn that she is unaware that her son is gay. |
| 02.09 | 31 | 11/30/1999 | Terms of Employment | Grace 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. |
| 02.10 | 32 | 01/11/2000 | Tea and a Total Lack of Sympathy | Will kisses up to Karen to appease his new boss; Jack and Grace get into hot water over an antique teapot. |
| 02.11 | 33 | 01/25/2000 | Seeds of Discontent | When an old school chum asks Will to father her child, a jealous Grace tries to thwart her baby-making plans. |
| 02.12 | 34 | 02/08/2000 | He's Come Undone | Will'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. |
| 02.13 | 35 | 02/15/2000 | Oh Dad, Poor Dad, He's Kept Me In The Closet and I'm So Sad | Will's father tells his colleagues that his son and Grace are married; Jack prepares to meet his biological father. |
| 02.14 | 36 | 02/22/2000 | Acting Out | Will 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. |
| 02.15 | 37 | 02/29/2000 | Advise and Resent | Will 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. |
| 02.16 | 38 | 03/07/2000 | Hey La, Hey La, My Ex-Boyfriend's Back | Will has designs on Grace's newest interior-decorating client--his ex-boyfriend; Karen tries taking her "career" more seriously. |
| 02.17 | 39 | 03/28/2000 | The Hospital Show | After Karen's husband suffers a heart attack, there is speculation on whom she will turn to for support. |
| 02.18 | 40 | 04/04/2000 | Sweet (and Sour) Charity | As 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. |
| 02.19 | 41 | 04/18/2000 | An Affair To Forget | Ellen learns at her bachelorette party that Grace once slept with her fiance Rob. |
| 02.20 | 42 | 05/02/2000 | Girls, Interrupted | Grace suspects Val may have stolen her music box; Jack plays straight to woo a heterosexual convert. |
| 02.21 | 43 | 05/09/2000 | There But for the Grace of Grace | Will and Grace are alarmed when the friendship of two bickering oldsters mirrors their own; Ben impresses Jack and Karen with his hidden talents. |
| 02.22 | 44 | 05/16/2000 | My Best Friend's Tush | Grace finds out that one of Karen's friends is her competition for an important interior design job. Meanwhile, Jack tries marketing an odd invention. |
| 02.23 | 45 | 05/23/2000 | Ben? Her? | Will discovers that Grace is dating his boss; Rosario requests a divorce from Jack so that she can be with Karen's Gardener. |