Jack reconnects with his teenage son, Karen faces upheaval in her extravagant lifestyle, and Will and Grace navigate their evolving friendship amid career and dating mishaps. Guest stars like Cher, Sandra Bernhard, and Woody Harrelson bring standout moments in this sharp and heartfelt season.
Will returns from vacation to discover that Grace's romantic relationship with neighbor Nathan is humming along. Nathan feels neglected when Will and Grace resume their chummy friendship, complete with their own private language and code. Meanwhile, Jack proudly takes his new-found son Elliot shopping for school at Barney's while Rosario and Karen each cruise the merchandise looking for the perfect "anniversary gift".
The new lawyer in Will's firm is the same lout who bullied him as a child; Nathan's birthday flusters Grace, who's outdone in the gift department by Karen.
Jack is puffed up with paternal pride as he escorts his long-lost teenaged son Elliot to a junior high school dance but not before he coerces Grace into posing as Elliot's date â€" 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"" â€" that is, until she really needs him.
After Stan is arrested for tax evasion, Grace and Karen timidly visit him in prison. 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 stage-fright 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. Jack 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. When she realizes her mistake, she returns the favor, but doesn't get the response she hoped she'd get.
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.
Will and Grace elect to disagree when it comes to choosing sides during a mayoral election; she supports the female Jewish candidate and he's voting for the gay nominee. To settle matters, the roomies host fund-raisers attended simultaneously by both aspirants.
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. (Double-length Episode)
At the gym, Will spies another guy who looks maddeningly familiar, while 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 moneyâ€"even if she has to resort to drastic measures to get the point across.
Grace is hired as seasonal help to decorate the Christmas display windows of fashionable Barney's; Will meets a ballet dancer but is too embarrassed to introduce his friends.
Will & Grace try to lure Tina, Will's dad's mistress, away from Will's father by setting her up with another man. Unfortunately the only man available is Will's gay friend, Larry. Also, Karen buys a horse for breeding, but the stud is more interested in stallions.
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 â€" 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.
Rosie O'Donnell plays Bonnie, a no-nonsense single mom who clashes with Jack over the raising of their son, Elliot, fathered from Jack's sperm-bank donation. Bonnie's enraged because Jack had 12-year-old Elliot's hair bleached blond, so she lays down the law. ""From now on,"" she tells him, ""stay out of my kid's life. I don't want you to see him again."" A parallel storyline unfolds at a wedding gala, where Will poses as a tennis pro (because nobody likes lawyers); and Grace caustically toasts the bridegroom, her ex-fiancé. ""I've always thought about having a child,"" she says. ""But not as a husband.""
Matt Damon makes a guest appearance as a clever charmer named Owen, who's competing against Jack for a spot in New York's Gay Men's Chorus. Truth be told, however, Owen is totally straight and is really after the group's big perk: a summer trip to Europe, all-expenses paid. Jack suspects Owen's ruse but needs proof. How about the hug test? Now a flustered Jack reluctantly turns to Grace to ""in"" Owen. 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 placeâ€"despite the efforts of Sandra Bernhardâ€"but to finance the move, they illegally sub-let their old apartment. 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 their friends who sub-let the place. Elsewhere, Jack tries to reconcile Karen with her estranged grifter of a mom, who wants to recruit her daughter for her next caper.
Will presents his newly reconciled parents with a cruise for their anniversary, but their individual secrets ruin his hopes.
In the aftermath of his parents' divorce, Will salvages a beloved garden gnome â€" nicknamed ""Squatsie"" â€" 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 for more meaningful gay acting gigs in the future.
Teaching a design seminar challenges Grace; chaperoning Jack's son occupies Will at the youth's basketball tourney.
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 â€" 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 â€" 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 â€" and frightens Will. Meanwhile, Jack's back with another performance act, and this time he employs magic tricks but regrets using Karen as his 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 â€" 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; 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 â€" 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 â€" 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.