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- Season 2 overviewSep 21, 1999-May 23, 200024 episodesSeason 2 episodes1. Guess Who's Not Coming to Dinner Sep 21, 1999
- Grace moves and gives a dinner party without Will's help.
- 2. Election Sep 28, 1999
- Grace decides to run against Will in an upcoming election for president of the board of tenants.
- 3. Das Boob Nov 2, 1999
- Grace gets attention after a newspaper publishes a photo in which she appears buxom.
- 4. Whose Mom Is It Anyway? Nov 9, 1999
- Grace gets jealous when her mother (Debbie Reynolds) dotes on Will.
- 5. Polk Defeats Truman Nov 16, 1999
- Will dismisses faithful clients after a powerful man inflates his ego.
- 6. To Serve and Disinfect Nov 23, 1999
- Jack challenges unemployed Will to join his staff as a caterer/waiter.
- 7. Homo for the Holidays Nov 25, 1999
- Jack hopes to reveal his homosexuality to his mother (Veronica Cartwright) over Thanksgiving dinner.
- 8. Terms of Employment Nov 30, 1999
- Will represents Grace against a lawyer who ends up making Will a job offer.
- 9. I Never Promised You an Olive Garden Dec 14, 1999
- Friends become jealous when Will and Grace begin hanging out with a hip young couple.
- 10. Tea and a Total Lack of Sympathy Jan 11, 2000
- Will must bring in a major new client by the end of the week or else lose his job.
- 11. Seeds of Discontent Jan 25, 2000
- Will's best friend from high school visits with an unusual request.
- 12. He's Come Undone Feb 8, 2000
- Will experiences strange dreams while Grace dates his therapist.
- Will learns that his father has been covering up Will's homosexuality.
- 14. Acting Out Feb 22, 2000
- Will and Jack complain to the "Today" show's Al Roker.
- 15. Advise and Resent Feb 29, 2000
- Will gets advice from Jack on how to handle a blind date arranged by his boss.
- 16. Hey La, Hey La, My Ex-Boyfriend's Back Mar 14, 2000
- Will's ex-boyfriend returns; Karen asks Grace for greater responsibilities at work.
- 17. The Hospital Show Mar 28, 2000
- Karen's husband has a heart attack.
- 18. Sweet and Sour Charity Apr 4, 2000
- Grace recruits Will to help at a community center; Jack donates Karen's shoes to charity.
- 19. An Affair to Forget Apr 18, 2000
- Grace confesses to Will that she once had an affair with Rob.
- 20. Girls, Interrupted May 2, 2000
- Grace suspects Val may have stolen her music box; Jack plays straight to woo a heterosexual convert.
- 21. There But for the Grace of Grace May 9, 2000
- Will and Grace visit an old college professor and get a scary look at their potential future.
- 22. My Best Friend's Tush May 16, 2000
- Karen's friend turns out to be Grace's competition for a job.
- 23. Ben? Her? May 23, 2000
- Without Will knowing, Grace has a romantic liaison with his boss (Gregory Hines).
- 24. Ben? Her? May 23, 2000
- Without Will knowing, Grace has a romantic liaison with his boss (Gregory Hines).
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