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- Gay lawyer Will and straight interior designer Grace share a New York City apartment. Their best friends are gleeful and proud gay Jack and charismatic, filthy-rich, amoral socialite Karen.
- When Grace admits she's not sure who's the father of her baby, Karen orchestrates a "Mamma Mia" situation with the potential baby daddies; Will worries what will happen if he has a straight son and enlists Jack to help him prepare.
- Will discovers a way to finally get back at Jack for years of mocking his hairline; Grace is determined to prove to Mrs. Timmer she's strong enough to handle being a single mother; Karen squares off against Stan's brother in a poker game.
- Will and Grace fight over whose process of having a baby is more difficult; Jack helps Karen prove that she'll be a competent owner of her new baseball team, but Karen realizes that an old acquaintance may be the help she really needs.
- In the aftermath of Will and McCoy breaking up, Grace and Jack hire the Grief Panda to help Will process his pain; with Karen completely occupied with her baseball team, Grace believes that she has to fire Karen in order to set her free.
- Committed to becoming a father on his own, Will meets a potential surrogate (Demi Lovato); to gain entry into AnnieCon, Grace pretends to be a formerly-famous Annie.
- Grace and her neighbor give their romance another shot, but an embarrassing incident puts Grace's relationship and dignity in jeopardy; Will cuts Jack off financially to get him to grow up.
- When Larry warns Will and Grace about the entry process into the elite school they want their kids to go to, they set out to prove that their child would be the better candidate; Jack creates problems between Karen and her booty buddy.
- Will and Grace decide to intervene when they discover Grace's niece is dating a bisexual man; Jack gets permission from his husband to sleep with his hall pass; Karen struggles to adapt when her assistant books them on an economy flight.
- Grace and her neighbor, James, give their relationship one more shot, but when James invites Grace to his job at the aquarium, she endangers his job and a species; Jack takes Will to an unexpected place to blow off steam -- church.
- Marilyn goes behind Grace's back to fix her up with a beagle-breeding couple interested in adopting Grace's baby; Will helps Karen deal with a PR nightmare; Jack and Estefan go to extreme lengths to get rid of a mouse.
- Karen introduces Will and Grace to the new love of her life. When Miss Coco Peru tells Jack that he's closing down his bar for good, Estefan encourages Jack to become its new owner.
- Will and Grace race to save Karen when they think she is in danger after her new boyfriend takes her to a cabin in the woods; Jack makes up a story to a reporter in order to keep his new bar relevant after its previous owner steps down.
- Jack helps Karen sneak into the manse to retrieve her ring, but they're shocked to find it on the hand of Stan's new girlfriend; while hosting Will's surrogate, Will and Grace become the old folks they swore they'd never become.
- Will ropes Dr. DiLorenzo into going on a fake date so he can spy on his surrogate; Grace struggles with popping her gender reveal balloon; Karen is torn between celebrating her team's championship and helping Jack with a Broadway audition.
- Will claims living with Grace is like Ricky living with Lucy; when Karen and Jack hear this, they each claim that they are the Lucy of the group; Grace, Karen and Jack each imagine themselves as Lucy, with Will as the Ricky to all of them.
- Karen celebrates her baseball team's championship; Will and Grace go to an open house, which leads to a conversation about their future living arrangement; Jack has to decide if he wants to stay in the city to pursue his dreams.
- Will is determined to not reminisce about his life in the city or his ex; Grace has false alarms of going into labor; Karen tries to get closure with her ex-husband; Jack's dream of taking a bow on a Broadway stage becomes a possibility.
- Eleven years after last being seen, Will and Grace's political beliefs are put to the test.
- Grace is shocked to find that the emergency contact called by her doctor's office is ex-husband Leo, not Will. Jack takes on a new job he never expected to love. Karen befriends a 12-year-old girl in the Bronx, despite her best efforts.
- Will starts dating a 23 year-old. Jack is worried about getting old and decides to try something new. Grace and Karen solve their differences about work in an automatic shower.
- 1998–202021mTV-PG8.1 (578)TV EpisodeGrace tries for her biggest job yet; Will is surprised to making Senior Partner; Beverley discloses his secret to Karen; Jack owns half of a winning lottery ticket.
- Karen has trouble dealing with a personal tragedy; Will, Grace, and Jack try to intervene; Will and Grace's new business relationship begins to show signs of stress.
- Will and Grace attempt to convince themselves it's okay to sleep with the same man; Jack and Karen get an annoying commercial jingle stuck in their heads.
- Will, Grace, Karen, and Jack wish they could have experienced Christmas in old New York City, but realize the past was not quite as romantic as they pictured it.
- Will and Grace's old friend Larry believes he's in love with Will; Val the clingy stalker is back, and she really wants Karen and Jack to be her friends.
- Will, Grace, Jack, and Karen attend the wedding of Will's ex-boyfriend Vince.
- Jack's closeted boyfriend challenges his intimacy issues; Will and Grace go on TV to sell their new line of bedding.
- Grace discovers she's dated three men from the same family. Meanwhile, Will and Karen develop their very own telenovela plot in the office while watching Karen's staff on her Home surveillance feed.
- Best friends, Will, who is a gay lawyer, and interior designer Grace, share an apartment and are constantly in each other's business. Stirring the pot of melodrama is Grace's "employee," Karen, and Jack, Will's flamboyant friend.
- 1998–202021mTV-147.9 (398)TV EpisodeA baby shower makes Grace and Will question their life choices; Karen and Jack find a way to combine child labor with musical theater.
- 20 Years after their break-up, Will and Michael reconnect and Grace observes.
- Grace brings Will for support when she goes home to celebrate her deceased mother's birthday; Jack's faith in love is crushed after a breakup; a secret in Karen's marriage is uncovered.
- Grace's father and Will's mother end up making a surprising and upsetting connection. Jack rebounds from his breakup with a new love. Karen must decide between her husband and her lover.
- 1998–202021mTV-147.7 (371)TV EpisodeWill, Grace and Jack realize they've been too preoccupied with all the changes in their lives to notice that Karen hasn't been seen since her husband found out about her affair with Malcolm.
- Will and Jack visit Jack's grandson, Skip, in Texas to watch him perform at his church's talent show. But when Jack learns Skip plans on singing "Diamonds Are A Girl's Best Friend," he becomes afraid for his grandson's safety. Karen tags along to check out the portion of the border wall she sponsored, only to discover that Beverley Leslie has claimed it as his own. Back home, Grace and Noah try to figure out if something is wrong in their relationship because their numerous attempts to have sex have failed.
- Will and Grace reminisce about old times and get into an argument. With the help of Jack and his new found gift, Karen is visited by an old friend who convinces her not to give up on love.
- Grace reveals a painful secret to her father; Will and Karen fight for the role of best man in Jack's wedding.
- Will discovers that Noah has a child he hasn't told Grace about, but is now sworn to secrecy. Karen and Jack's relationship is tested when she fires him from the play she's producing and replaces him with Jon Cryer.
- Grace unintentionally meets Noah's daughter Katie; Will's mom Marilyn visits after the death of her beloved dog, but doesn't get the emotional support she expects; Jack argues with his rec center boss, Theo.
- In order to land a handsome, gay TV news anchor with a pension for dim, frothy men, Jack convinces Will to not be himself and to act like someone silly and stupid. Karen learns that her alimony will be severely limited unless she can get photos of her ex-husband's affair with Lorraine Finster, so she enlists Grace to go with her to the strip club where Lorraine works. Olympian Adam Rippon has a cameo as a barista with an attitude.
- Will, Karen and Jack unknowingly take hallucinogens, which cause Will and Jack to wonder whether they're soul mates and have Karen giving her final performance as Mrs. Stanley Walker; a high-powered client takes up with Grace's sister Janet.
- Will and Grace's plan to win over Will's new Columbia department head goes awry when he drops dead in their apartment - and they use his phone to text his full recommendation of Will. Karen and Estefan's dislike for each other puts Jack in full damage control mode when he must keep them separate at his birthday dinner.
- When Will discovers Karen's estranged stepdaughter Olivia is a student in his law class, he attempts to solve their issues with a mock trial. Grace and Jack go on a diet together, but giving up their eating habits proves harder than anticipated.
- Malcolm enlists Grace to help him win back Karen's affections. Will's flirtation at work lands him in an ethical dilemma. Jack's passion for performing is reignited by a chance encounter with Zusanna, the sister of his former acting teacher.
- Will gives local newscaster McCoy Whitman a second chance and, with the help of Jack, finally gets to know the man behind the newsman. Grace's campaign for Design Guild President hits a snag when the deciding vote comes down to her old nemesis, Val. Karen acts as Grace's campaign manager, and attempts to secure Val's vote by any means necessary.
- Grace returns from her travels a new woman, but her elation is short-lived when she receives life-changing news; Karen teaches Will how to be better at phone sex; Jack has a yard sale to discreetly get rid of Estefan's cuckoo clock.
- Jack's insistence that Will be nicer to his fiancé, Estefan, backfires when Estefan thinks Will is in love with him. In a hurry to buy her boyfriend Noah a Valentine's Day gift, Grace unknowingly knocks over a prominent figure while going after a taxi. And when Karen discovers that Noah not only writes her favorite romance novels but also plans to kill off the main character, she forces him to rewrite the story.
- After her dad, Martin, is rushed to the hospital, Grace is shocked when he refuses a transfusion of Will's blood. Will's mom, Marilyn, uncharacteristically takes Martin to task. Karen's demands cause Jack to uninvite her to his wedding.
- When both of their boyfriends ask to move in, Will and Grace use each other as an excuse to get out of it. A snowstorm traps Karen at the office and Jack in an elevator, where he reunites with old flame Drew and tests his commitment to monogamy.