Grace gives romantic advice to her slovenly new neighbor Nathan in hope of reuniting him with his girlfriend so he will move away. Meanwhile, Will and Jack are out on the town with an unwelcome chaperone: Karen’s oblivious mother-in-law.
An exasperated Grace tries to mediate between a resentful Will and her sloppy, free-spirited boyfriend Nathan when Nathan moves in while Jack is in a royal dither as he plans to finally meet his unseen father face-to-face. However, Grace grows nervous when the two polar-opposite men find some common ground and she ponders how a devoted boyfriend might affect her equally important relationship with her longtime buddy Will. After settling his father issues, Jack later gets the surprise of his life in a most unexpected fashion.
Grace hates herself for her fatal attraction to Nathan and wants to keep her embarrassing romance with him a secret. Likewise, Will prefers to maintain discretion in his relationship with a much younger man. Meanwhile, Jack revels in the attention lavished on him by Grace’s eccentric friend, Val.
When Grace learns that an old school mate who she made fun of has died, guilt makes her attend the funeral. Meanwhile, Jack is nominated for a gay cabaret award.
Grace gives romantic advice to her slovenly new neighbor Nathan in hope of reuniting him with his girlfriend so he will move away. Meanwhile, Will and Jack are out on the town with an unwelcome chaperone: Karen’s oblivious mother-in-law.
When Grace frets that she and Will might drift apart like their similar friends, she impulsively buys an expensive piano which she hopes will cement their mutual bond and love for music – or at least give her an excuse to perform a lot of show tunes. Meanwhile, when Jack is dumped by his latest romantic interest, he vents his grief by writing trashy novels which instantly draw Karen’s passionate attention.
First aired: 3/29/2001 Production Code: 63817
Grace’s lousy poker playing leads Will’s friends to ban her from the game, but Grace makes an amazing turnaround to stay in; Karen uses a snippy socialite as a guinea pig for cosmetic surgery.
Grace is smitten when she meets Sumner, Karen’s charming and handsome nephew, but Grace’s attempts to arrange a date are constantly thwarted when Karen conjures up a litany of lies to dissuade her. Meanwhile, Will tries to terminate his dead-end relationship with a needy nebbish, but postpones the dramatic moment because he’s so infatuated with the guy’s lovable doggie, Pepper.
Grace is apologetic when she catches Will’s philandering father on the arm of a glamorous stranger, but she gets even more worked up when she tells Will — and he’s happy living with denial. Speaking of cheaters, Karen misunderstands Grace and suddenly suspects that her husband Stan is having an affair, so she sets out to even the score.
Grace dispatches Will to sell her dearly departed uncle’s jalopy but after he makes the sale to an enterprising nun, a guilty Grace changes her mind and wants to buy it back — but the sister makes it clear that, short of a miracle, it’s going to cost her plenty. Elsewhere, Karen must duel with an equally eccentric rich friend for the housecleaning services of Rosario while Jack suddenly sees the world differently when he believes his missing father is African-American.
Will is torn over ending his newfound relationship with Matt, a rising TV sportcaster who is extremely reluctant to let the world – especially his macho business associates – know about his sexual preference, so he continues to refer to Will as his “brother.” Meanwhile, as Grace does her best to help Will decide, Karen is livid when she discovers that he helped draft her husband’s will, which will award much of his estate to charity.
A sports-challenged Will tries to impress his new friend Matt – a sportscaster – with his athletic skills by checking into a batting cage but it takes Grace to show him how to improve his swing. Meanwhile, Grace is given a mission: impossible when Jack and Karen ask her to exotically re-decorate Jack’s apartment.
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.
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.
Just as Grace seems to be on the verge of a promising relationship, she undergoes a minor medical procedure that leaves her with an embarrassing ugly sore on her lip, but even though her new beau accepts her temporary blight, she cannot return the favor when she is horrified to learn he has six toes on one foot. Meanwhile, Will vies with Jack for the attentions of the same man until each agrees to walk away to preserve their friendship.
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 teenaged Jack for some crucial advice. Unfortunately, Will and an angry Grace end up temporarily estranged when he blurts out the truth and she orders him out of the house — and her life.
Will reluctantly decides to use a birthday gift certificate from Grace to consult a psychic about his future and encounters an absent-minded fortune teller whose frighteningly personal predictions leave him reeling. Elsewhere, a guilt-ridden Grace hires a lackadaisical waiter whom she helped to get fired while Jack, who forever idolizes music, TV and film legend Cher, stumbles onto the real deal and meets the Oscar winner herself — whom he mistakes for a drag queen.
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.
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.
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.
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.
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.
After three months on the island, Will finally returns only to learn that Jack and Grace have bonded in his absence. Meanwhile Grace still can’t decide between Josh and Ben; When Karen tries to smuggle pearls in the States, Rosario ends up taking the rap.
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