Will returns from vacation to discover that Grace's romantic relationship with neighbor Nathan is humming along -- but Nathan feels neglected when Will and Grace resume their chummy friendship, complete with their own private language and code. Meanwhile, Jack proudly takes his newfound son shopping for school at Barney's while Rosario and Karen each cruise the merchandise looking for the perfect anniversary gift.
Will has a fearsome flashback when a former classmate who once tormented him as a kid now joins his law firm as a fellow attorney -- and resumes his evil childhood harassment. Meanwhile, Grace feels shamed when she gives Nathan a birthday gift that is dwarfed by one from Karen.
Jack is puffed up with paternal pride as he escorts his son Elliot to a junior high school dance but not before he coerces Grace into posing as Elliot's date -- which only revives her own tortured memories of rejection from school dances many years before. Elsewhere, Karen has great fun at her lawyer Will's expense when she continues to capriciously summon him for bogus 'emergencies' -- that is, until she really needs him.
After Stan is arrested for tax evasion, Grace and Karen timidly visit him in prison, but Grace is so moved to help her worried friend that she moves right into Karen's deluxe apartment in the sky -- where she becomes a demanding guest who's soon hooked on servants, bubble baths and an extravagant lifestyle. Meanwhile, as Stan's attorney, Will struggles with stagefright when he babbles on during a TV news interview, so Jack convinces him to polish his communication skills by attending an acting class ruled by an imperious teacher.
In a sneaky ploy to bum a night off from work at Barney's department store, a conniving Jack plays matchmaker and takes advantage of his geeky female supervisor's interest in Will -- while mindful of Will's fantasy of modeling in the store's catalogue -- and he parlays their mutual desires into a 'date,' even though his unsuspecting friend doesn't have a clue of her intentions. Elsewhere, Grace goes where no woman should when she compares her previous sexual experience with her boyfriend Nathan's.
During an intimate moment, Nathan pops the question of marriage to Grace but she recoils simply because the situation didn't fit her childhood fantasy of a proposal -- and when she realizes her mistake, she intends to return the favor and send out invitations. Meanwhile, Will tries to soothe Grace's ruffled feathers while engaging ethically challenged Jack and Karen over the proper rules of tipping and tippling at bars.
While a baleful Grace wallows in bed as she grieves over losing her boyfriend Nathan, an enterprising Will tries all his old tricks to spring her from her mattress and back into the real world's whirl. But when Jack and Karen arrive, Will fears that their bizarre efforts to help might actually drive Grace futher into her shell -- not to mention therapy.
Political na?vet? finds Will backing a city-council candidate because he's gay, and Grace behind another because she's a Jewish woman. To settle matters, the roomies host fund-raisers attended simultaneously by both aspirants. Meanwhile, Jack struggles to make Karen and Elliot get along.
Rather than be apart on Thanksgiving Day, Will and Grace join Jack and Karen for a festive holiday motor tour of their respective dysfunctional families, including Grace's domineering mother as well as Will's willful mom and Jack's stepdad -- with unsettling results. Meanwhile, back home, a waiting Rosario bastes and tastes their juicy turkey.
This episode is also known as "Thanksgiving". Will and Grace join Jack and Karen in a motor tour of their respective families.
Will spies another guy who looks maddeningly familiar while elsewhere at the gym, Jack gets a workout as he keeps repeating one of his nonsensical catchphrases in hopes of seeing it become popular among the sweat set. Meanwhile, Grace gets some bad advice from Karen when she seeks a loan to expand her company so she stoops to asking her wealthy employee herself for the money -- even if she has to resort to drastic measures to get the point across.
During the holidays, Jack's boss Dorleen allows him to decorate a Barney's display window, while Will meets a ballet dancer but is too embarrassed to introduce him to his friends.
While buying holiday gifts, Grace schemes to fix up the giggling mistress of Will's father with a friend as a favor to Will in hopes that she will abandon his old man -- but the scheme dreadfully backfires when they are forced to press a gay friend into service as a date at the last minute. Meanwhile, Jack and Karen have no horse sense when they buy a nag for breeding and expect a financial windfall.
While visiting Karen's incarcerated husband, Grace re-discovers a handsome high school friend who's also doing time in prison, and despite Will's advice, she's soon dressing up and visiting the inmate while dreaming of a life together outside the Big House. Conversely, a sympathetic Rosario chides Karen for not standing by her man -- and bets her boozy boss that she and pal Jack cannot stay penned-up together in the same room for three days without harming each other.
When Grace is invited to her ex-fianc?'s wedding, she hauls along a reluctant Will just to convey a false air of success -- but when she denigrates the bridegroom's faults at the rehearsal dinner, she's confronted by a weeping bride-to-be who now wants to flee. Meanwhile, Elliot's fuming mother gets in Jack's face when he allows Elliot to frost his hair and demands that he never see his son again. In addition, Will poses as a swinging tennis pro until he meets his match.
A desperate Jack seeks to 'in' his rival for the last spot in the Manhattan Gay Men's Chorus that will tour Europe by dangling a motivated Grace as date-bait before him to prove that he's actually straight. Meanwhile, a scheming Karen tries to pass off an unwitting Will as her lover and not her lawyer when she discovers that she's the object of pity for being single at her own Valentine's Day party.
Will and Grace feel they need more elbow room, so they search for larger digs and find an exquisite place -- despite the efforts of Sandra Bernhard -- but to finance the move, they illegally sub-let their old apartment to their friends. Meanwhile, a well-intentioned Jack begins filming a documentary of Karen's colorful life to celebrate her birthday but accidentally stumbles upon her estranged, lowlife mom.
After Will and Grace move into their expansive new dream apartment, they discover the awful pangs of separation anxiety as they pine for their smaller old digs now happily occupied by Rob and Ellen. Elsewhere, Jack tries to reconcile Karen with her estranged grifter of a mom who wants to recruit her daughter for one last scam.
An excited Will presents his newly reconciled parents with a romantic cruise on their anniversary -- but his idealistic plans are scuttled when he learns that each is hiding a secret. Meanwhile, due to Karen's phobia about an elevator, she and Jack huff and puff their way up dozens of floors to the skytop restaurant while hefting the prized anniversary cake.
In the aftermath of his parents' divorce, Will salvages a beloved garden gnome -- nicknamed 'Squatsie' -- and proudly plants the childhood relic in his apartment's community area until Grace accidentally delivers a coup de grace on the gnome's dome with a shovel. Elsewhere, Jack consults his acting coach when he fears that his heterosexual role in a mattress commercial produced by Karen will stereotype him from more meaningful gay acting gigs in the future.
When Jack has to work, he asks Will to escort his son Elliot to join other fathers in a weekend basketball tournament in Connecticut -- but Jack later goes ballistic when he learns from Will that he missed the teen's first kiss with a female student. Back in town, Grace plays schoolmarm in a New School design class full of attention-deprived slackers who would rather discuss celebrity houses than listen to her drone on.
Will expects two friends to arrive in New York to plan a wedding, but when the bride-to-be falls ill, he asks a willing Grace to work with the clueless groom to work out the details -- but she gets a little too involved in the dreamy details and fancies herself a bride instead. Meanwhile, Will and Karen get chummy over a steamy potboiler book that they're both reading which leaves a jealous Jack fuming as the odd man out in the book-of-the-month club.
After his laptop computer is stolen, Will meets a sociable police detective who takes a special interest in his case as they go undercover -- but Will doesn't know that the gumshoe is secretly participating in Jack's therapy group for gays. Elsewhere, Grace is again hassled by her psycho neighbor Val who opens a rival design business and prospers by stealing Grace's ideas.
After Will wins a portrait session at a charity auction, he takes Grace to pose for a notoriously eccentric celebrity photographer but the unfocused shooter's bizarre methods ultimately produce a funky image that flatters Grace -- and frightens Will. Meanwhile, Jack's back with another performance act, and this time he employs magic tricks but regrets using Karen as his less-than-helpful assistant.
When Will hears his 'biological clock' ticking, he shocks Grace by asking her to become the mother of his baby but when they meet with a therapist, Grace reveals that she's uneasy about the necessary sacrifices -- and makes a startling revelation. Inspired by Will's 'seize the day' quest, Jack and Karen are also moved to pursue their goals: for him, it's auditioning for a legitimate Broadway production, and for her, it's visiting her imprisoned husband for a dreaded conjugal visit.
After Will and Grace decide to have a baby together, obstacles pile up before them, including a missing specimen sample and bungled insemination efforts that have them teetering between artificial and natural means -- all leading to mis-conceptions. Meanwhile, when Jack considers giving up his show-business aspirations, until he gets some career advice from a 'divine' entity -- his idol, Cher. Likewise, married Karen is sorely tempted by the romantic tickling of a rich and natty gentleman.
After Will and Grace decide to have a baby together, obstacles pile up before them, including a missing specimen sample and bungled insemination efforts that have them teetering between artificial and natural meansâ-all leading to mis-conceptions. Meanwhile, Jack considers giving up his show-business aspirations, until he gets some career advice from a "divine" entity: his idol Cher. Likewise, married Karen is sorely tempted by the romantic tickling of a rich and natty gentleman.