Will is still on the Island with Karen, Stan and Rosario. Grace is wanting his advice to which guy she should be with, Josh or Ben, Jack helps her out and says she should be with Ben as there is something about Josh that he can't put his finger on , Will gets mad with Karen and feels he should be home helping Grace, Will, feels left out within what happened in the last 3 months Grace and Jack have started to become closer friends, also he tells her that she should Josh. Karen trying to smuggle in drugs but blames it on Rosario and feels guilty about it but doesn't ...

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Terrified after someone breaks into her apartment, Grace stays with Will. Unfortunately, having both her and Jack under one roof is driving Will crazy and he forces them to choose which one will move out; Jack and Karen are still at odds over his divorce from Rosario.

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Will and Jack can't wait to arrive at the house of two old friends who are known for their wild parties but they discover that the former party animals are now sedately raising an adopted baby girl -- and Will shocks Jack when he volunteers to test his shaky parenting skills by babysitting her for them. Elsewhere at a snooty yacht club, Grace believes that Karen is jealous of her romantic relationship with Ben but then later regrets taunting her.

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Grace's delight in having a bright intern whom she can mentor turns into horror when the young woman re-makes herself into the spitting image of sassy, brassy Karen -- and that's at least one too many Karens to handle. Meanwhile, Will and Jack volunteer to act out scenes for a gay sensitivity seminar for the local police but the peaceful intent is lost when they tussle with two lesbian cast members who strongly object to their non-inclusive, sexist language.

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Grace has made up her mind to break up with Ben because she's convinced their relationship is going nowhere -- but his charm and refusal to call it quits tempt her to reconsider. Meanwhile, Jack's latest and most outrageous cabaret gig is an absolute bomb until he frantically works an unwilling Will into the act by mercilessly ridiculing his attending friend's most-private confessions.

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Grace rejects an ex-boyfriend's suggestion that she participate with him and his girlfriend in a romantic escapade but when she confides in Will and Karen -- who fall down laughing at the prospect -- the conservative Grace considers throwing caution to the wind. Meanwhile, Will tries to help a newly employed Jack meet a customer at a clothing store by prompting him with witty lines like a latter-day Cyrano de Bergerac.

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Grace gives Will a gift certificate for his birthday for a psychic reading. Will goes, and when she says something that he thinks is impossible, he leaves. Later her predictions come true, so he goes back and asks her about his love life and she predicts he will be with someone whose name begins with "J". Will assumes it's Jack which freaks him out. Grace gets a waiter fired from his job so she hires him. Unknown to her, the guy is doing something in her office.

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In a flashback to Thanksgiving 1985, coed Grace invites her college boyfriend Will home to meet her family, but their romantic relationship swerves dramatically when a conflicted Will phones a teenage Jack for some crucial advice. We also learn why the famous tennis player Martina Navratilova became a lesbian.

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The flashback to Thanksgiving 1985 continues, and when Will finally tells Grace the truth, she orders him out of the house -- and her life. Meanwhile, Karen meets someone who will become a permanent fixture in her life.

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Grace has medical procedure that leaves her with a sore on her lip and when she runs into her new boyfriend she does her best to avoid him but decides to come clean. He also does the same, by telling her he has 6 toes on one of his feet. And when they spend some time alone, he decides to take his shoe off and she becomes uncomfortable. Will and Jack discover that they're seeing the same guy who was unaware of their connection. So they decide to both bow out but the guy keeps calling Will, and Grace convinces him that Jack will understand.

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When they are asked to read at the civil union of two friends, Will and Grace verbally spar over her self-serving, get-and-take attitude where Will is responsible for everything -- but what's really bugging him is the overwhelming feeling that Grace is behaving more like a wife than an old friend. Meanwhile, Karen tries to help a caffeine-addicted Jack get over a failed crush but he's so jacked-up on Java that only a tough-love approach will work.

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Will and Grace get carried away in an escrow undertow when they pose as a wealthy couple shopping for homes of the rich-and-famous and visit Sandra Bernhard's posh townhouse where they become fast friends and make an fake offer -- but their ploy fizzles when she accepts their offer. Elsewhere, Karen is forced to attend her young stepson's swim meet and is uncharacteristically chastised by another mother for arriving late while Jack begins attending Co-dependents Anonymous meetings.

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Will wanting to impress his new boyfriend who's a sport enthusiast asks Grace to teach him about sports starting with hitting a ball which he does terribly. Jack and Karen asks Grace to decorate Jack's apartment and initially they're difficult when she makes her proposal. But when they see a phony letter Grace made to get out of jury duty which states that she's mentally unbalanced, they give in to her demands not to upset her.

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Will gets upset when his new boyfriend refuses to recognize him as his boyfriend when they're in public and introduces him as his brother. Grace tells him he should dump him but Will finds it difficult to do that. And Karen discovers that Stan is giving a portion of his estate to charity in his will.

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Jack receives a letter that indicates he is black. Grace inherits an old a car from a deceased uncle. She sells the the car that she believes to be a lemon to a nun. Meanwhile, Karen discovers that Rosario is moonlighting for Beverly Leslie. Grace realizes that she should have kept the car and tries to buy it back.

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Grace is apoplectic when she catches Will's philandering father on the arm of a glamorous stranger.

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Will must face the truth about his father's affair.

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Will is dating a guy who is not exactly attractive because he is fond of his dog. Will takes care of the dog while he's away and when Jack loses him, Will doesn't know what to do. Grace meets Karen's nephew and she keeps Grace from dating him by telling lies. Grace thinks Karen doesn't think she's good enough for him.

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Will and Grace play poker with Larry, Rob, and Joe but because of certain annoying habits, the guys want Grace out and tell Will he has to tell her. Will tells her and she tries to change, when she does, she tells Will what she's doing. Karen wants to have plastic surgery but she wants to see it done on someone else first. So she gets an acquaintance to have the procedure first.

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Graces fears Will is pulling away, so she buys a piano for them to bond over. Meanwhile Jack is depressed over a recent breakup and channels his energy into writing roman novels, which Karen quickly becomes addicted to.

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Grace's (Debra Messing) new neighbor, guest star Woody Harrelson, is a slovenly lout whose disheveled lifestyle and grungy habits put him at odds with her well-ordered world.

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Will and Grace attend a funeral so that Grace can apologize for belittling a former classmate years ago. Also Jack gets ready for a gay cabaret award event with the help of Karen.

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Grace (Debra Messing) hates herself for her fatal attraction to a boorish neighbor (Oscar-nominated guest star Woody Harrelson), and wants to keep her newborn romance with him a secret.

Grace struggles trying to get Nathan and Will to get along, while Jack prepares to meet his birth father.

Will and Grace's relationship threatens the one she has with Nathan. Still heartbroken over the news about his real father, Jack also learns that he himself is a daddy, and not in the way he'd like.