Season 2

01 Guess Who's Not Coming to Dinner Episode 121st September 1999 Despite her moving out (to across the hall), Will still feels that Grace clings to him, so she asserts her independence by having a dinner party without him. Meanwhile, to keep the INS at bay, Jack is forced to move in with Rosario. 02 Election Episode 228th September 1999 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. 03 Das Boob Episode 32nd November 1999 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. 04 Whose Mom Is It Anyway? Episode 49th November 1999 Grace 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. 05 Polk Defeats Truman Episode 516th November 1999 When 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. 06 To Serve and Disinfect Episode 623rd November 1999 An 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. 07 Homo for the Holidays Episode 725th November 1999 Will 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. 08 Terms of Employment Episode 830th November 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. 09 I Never Promised You an Olive Garden Episode 914th December 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. 10 Tea and a Total Lack of Sympathy Episode 1011th January 2000 When 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. 11 Seeds of Discontent Episode 1125th January 2000 Grace 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."" 12 He's Come Undone Episode 128th February 2000 Erotic dreams about Grace send Will to a therapist, who seems more interested in Grace. Meanwhile Jack and Karen clash over her treatment of Rosario. 13 Oh Dad, Poor Dad, He's Kept Me in the Closet and I'm So Sad Episode 1315th February 2000 Will'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. 14 Acting Out Episode 1422nd February 2000 Will 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. 15 Advise and Resent Episode 1529th February 2000 When 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. 16 Hey La, Hey La, My Ex-Boyfriend's Back Episode 1614th March 2000 Will 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. 17 The Hospital Show Episode 1728th March 2000 While 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? 18 Sweet & Sour Charity Episode 184th April 2000 After 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. 19 An Affair to Forget Episode 1918th April 2000 When 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. 20 Girls, Interrupted Episode 202nd May 2000 Despite 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. 21 There But for the Grace of Grace Episode 219th May 2000 It's a scary glimpse into the future for Will and Grace when they visit their curmudgeonly retired college professor only to discover that he is a bitter old man that has a ""Grace"" of his own. Meanwhile, Karen must confront her most mortal enemy, the kitchen, when Stan requests a homecooked meal for his birthday, and she looks to Jack and Ben to come to her rescue. 22 My Best Friend's Tush Episode 2216th May 2000 Grace 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. 23 Ben? Her? (1) Episode 2323rd May 2000 To 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. 24 Ben? Her? (2) Episode 2423rd May 2000 Forced by his boss to betray both of his friends, Will quits--only to discover that everything isn't as it seems. Frustrated, he leaves a lost Jack and Grace behind and ends up on a tropical island without a care in the world. Until Ben shows up.