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Episodes
Season 2 - Episodes
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S02E02Election
Aired: 1999-09-28
Show details expand_moreWhen 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.
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S02E03Das Boob
Aired: 1999-11-02
Show details expand_moreA 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.
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S02E04Whose Mom is It Anyway?
Aired: 1999-11-09
Show details expand_moreGrace is jealous when her mother stops match making for her, and instead sets Will up. Jack must convince an INS agent (who he dated once) that he and Rosario are happily married.
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S02E05Polk Defeats Truman
Aired: 1999-11-16
Show details expand_moreWhen his work for Harlin takes up all his time, Will drops all his other legal clients; a decision that later comes up to bite. Meanwhile Grace tries to teach Karen how to live on a budget.
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S02E06To Serve and Disinfect
Aired: 1999-11-23
Show details expand_moreAn unemployed Will agrees to serve as one of Jack's cater-waiters, until he learns that he'll be catering for American Bar Association. Grace discovers Karen's darkest secret: she once made a porn video.
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S02E07Homo For the Holidays
Aired: 1999-11-25
Show details expand_moreWill and Grace are shocked to learn that Jack never told his mother he was gay and encourage him to open up to her at Thanksgiving. The evening brings a revelation for Jack as well: his father isn't who he thinks it is.
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S02E08Terms of Employment
Aired: 1999-11-30
Show details expand_moreGrace 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.
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S02E09I Never Promised You An Olive Garden
Aired: 1999-12-14
Show details expand_moreTired 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.
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S02E10Tea and a Total Lack of Sympathy
Aired: 2000-01-11
Show details expand_moreWhen they appear on their favorite TV show, Antiques on the Road, Grace can't wait to dress down the guests who are ever hopeful that their tchotchkes are worth a fortune, while Jack just wants to undress the show's attractive appraiser, Porcelain Paul. But then it's all business when they realize that their junky, thrift-store teapot is actually valued at $30,000. Meanwhile, Will's new boss makes the reluctant lawyer kiss up to Karen in hopes of landing her hubby as a client.
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S02E11Seeds of Discontent
Aired: 2000-01-25
Show details expand_moreGrace is excited to meet Will's best friend from high school until she learns that the woman has made a request: to be implanted with Will's sperm. Now Grace has to confront Will about Will being her "backup."
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S02E12He's Come Undone
Aired: 2000-02-08
Show details expand_moreErotic dreams about Grace send Will to a therapist, who seems more interested in Grace. Meanwhile Jack and Karen clash over her treatment of Rosario.
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S02E13Oh Dad, Poor Dad, He's Kept Me in the Closet and I'm So Sad
Aired: 2000-02-15
Show details expand_moreWill'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.
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S02E14Acting Out
Aired: 2000-02-22
Show details expand_moreWill and Jack appear on Today to protest NBC for cutting a gay kiss out of an eagerly-waited sitcom episode. Will is frustrated with Jack on how much he wanted to see that kiss and kisses him. Elsewhere, Grace confides in Karen about dumping her boyfriend.
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S02E15Advise and Resent
Aired: 2000-02-29
Show details expand_moreWhen 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.
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S02E16Hey La, Hey La, My Ex-Boyfriend's Back
Aired: 2000-03-14
Show details expand_moreWill 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.
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S02E17The Hospital Show
Aired: 2000-03-28
Show details expand_moreWhile 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?
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S02E18Sweet and Sour Charity
Aired: 2000-04-04
Show details expand_moreAfter 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 conficts with the concert. Meanwhile, while collecting clothes to give to the mission, Jack donates a pair of Karen's most-prized shoes.
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S02E19An Affair to Forget
Aired: 2000-04-18
Show details expand_moreWhen 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.
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S02E20Girls, Interrupted
Aired: 2000-05-02
Show details expand_moreDespite their history, Grace spends a fun evening with Val [ from ep. # 18 Grace, Replaced] 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.
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S02E22My Best Friend's Tush
Aired: 2000-05-16
Show details expand_moreGrace 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.
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S02E23Ben? Her? (1)
Aired: 2000-05-23
Show details expand_moreTo 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.












































