Will's poker night with his buddies gets interrupted by the unexpected arrival of Grace, who has once again broken up with her boyfriend and arrives to spend the night--much to the displeasure of Will's friend Jack, who was planning to move in temporarily while his own apartment has new flooring put in. Will talks Grace into finally leaving her boyfriend for good, she marches off to confront him, but when she returns to announce that she has accepted a marriage proposal, Will risks their friendship by telling her what he thinks.
Will and Grace's friendship becomes strained when he encourages her to find a place of her own--and then quickly discourages her idea to move in with him. Meanwhile, Jack's eccentricities are driving Will out of his mind.
Tensions escalate between new roommates Will and Grace when Grace has a giant hissy fit about her bathroom and insists on merging the adjoining bathroom without Will's consent, despite the fact he owns the apartment. Meanwhile, Will helps Jack with his résumé.
Grace reluctantly agrees to decorate Harlin's new apartment and she gets carried away with the cowboy theme. Meanwhile, Jack plays the diva role to the hilt when he auditions for a one-man show ("Just Jack") at a nightclub, with staging advice from a reluctantly intrigued Karen.
Will and Grace plan to spend a serious Halloween together watching Ingmar Bergman movies at home--until Harlin drops off his over-eager kids at their place when he's called away on business. Meanwhile, Jack convinces Karen to accompany him to the downtown parade where she becomes an honorary drag queen.
When Karen goes on vacation for a week, Grace hires Jack as her assistant. After Jack discloses Will's past affair with a "client," Grace worries that Will is keeping secrets from her. Meanwhile, Karen ponders leaving her husband and turns to Will for some legal help.
Grace claims that the reason she's not dating is that she's having too much "fun" with Will--so she proposes that they try their best not to have fun. Meanwhile, Jack is seeing stars over seeing an IRS agent, so he enlists Will's help.
Grace has the opportunity to buy her studio space from her building's owner. Since savvy lawyer Will is a tough negotiator, she asks him to help her with the offer. Grace thinks the whole deal will be a piece of cake, so she's shocked at the tactics Will has to use to get the price down. Meanwhile, Jack decides to become a massage therapist and asks Karen to be his "guinea pig" for his training. Although reluctant at first, Karen discovers that Jack has a real knack with her back--and wants him all to herself.
After Grace defies Will's wishes and brings home a puppy, Will can't resist the pooch and begins to treat him like a newborn baby. Meanwhile, Jack and Karen worry about the dog's effect on Will and Grace and insist that the new parents go out for a night on the town.
After Will installs a new heating vent in the apartment, he and Grace become obsessed with eavesdropping on the marital problems of the couple downstairs. Meanwhile, Jack's new career this week is playwriting and he enlists Karen's help in staging a play to bring them back to reality.
Grace and Jack, who have discovered a shared love for figure skating, get tickets for a hot ice show on the night they were planning to celebrate Will's birthday. An ice show is the last place Will wants to spend the evening, but he goes along to please his pals, accompanied by an even more reluctant Karen.
While Grace is pulling her hair out over an important showcase attended by critics, Will hires a maid whose presence changes Grace into a creative dynamo. Meanwhile, Jack pretends to be a lawyer to impress a handsome suitor.
Grace gets a visit from her critical, over-the-top mother, a would-be star whose propensity for breaking out into show tunes and impersonations dismays her daughter -- and delights Will, Jack and Karen. She also wreaks havoc by suggesting Will and Grace wed, despite their sexual differences. When Will winces at the fantasy of committing to anyone who needs to be the star of a relationship, it's an eye-opener for Grace, who sees she's more of a chip off the old block than she imagined. Meanwhile, Karen thinks she might be pregnant so Jack helps her take a pregnancy test.
Determined to mend their relationship, Grace surprises Will by inviting his estranged, older brother to Jack's birthday party. Will gets angry, but Grace may be too attracted to big brother to care.
Grace incurs Will's wrath when she spills the beans about her fling with his brother Sam. Karen goes into serious caring-friend mode, helping Grace sort out her feelings for both brothers and helping to guide Jack through the terrors of turning 30.
When a good-looking but sexually ambiguous new tenant moves in, both Will and Grace vie for his attentions until the competition grows so nasty it threatens their own relationship. Meanwhile, Karen has to fire her driver.
The gang roughs it in Karen's Vermont cabin in order to take Will's mind off what would have been his anniversary with his ex-boyfriend, Michael. Grace rekindles a romance with an old high-school flame and tries to hide the fling from Will. Meanwhile, Karen's culinary efforts go up in smoke, as does Jack's attempt to cheer Will by dragging him to a gay pub.
When Grace's job forces her to work overtime, Will feels utterly neglected. He seeks solace in the company of a new neighbor, Val, a recent divorcee who matches Grace quirk for quirk. At first, Grace seems oblivious to their camaraderie until Karen warns her of impending danger. Meanwhile, Jack is annoyed that he has to perform community service for slapping a meter maid, but he's even more horrified at the uniform he has to wear.
When Jack's gym membership is taken away, Grace suggests -- to Will's horror -- that Jack use the guest pass to Will's gym. When Jack joins Will to work out, Will becomes embarrassed to be seen with him. Meanwhile, Grace has a heart-to-heart with Karen.
A successful and arrogant New York publicist hires Grace to decorate his house with the condition that she fixes him up with Will. But there's a problem: Will can't stand the guy. Meanwhile, Jack uses Karen to teach Will how to kiss someone he finds unattractive.
When Rob and Ellen admit that they don't have fun playing games with Will and Grace because of Grace's competitive nature, Grace works to change her image. However, as Grace loses her competitive edge, Will's emerges and he convinces his partner to care only about winning. Meanwhile, Karen saves a workman's life after learning how to administer CPR from Jack.
Will is stunned to discover that Grace is dating her ex-fiancé Danny once again, but he chooses not to interfere after he's accused of being meddlesome. Meanwhile, Jack agrees to take a walk down the aisle with Karen's combative maid, Rosario, who needs a groom to help her smooth out some immigration problems.
After a newly independent Grace moves into an apartment across the hall, she decides to throw a dinner party all by herself. Will isn't invited, but he has a date. Meanwhile, to solve problems with the INS, Jack moves in with his new bride Rosario in the maid's quarters at Karen's.
Grace gives Will a run for his money when she enters his unopposed race to be named tenant-board president after she finds out about the position's perks. Meanwhile, Jack hits the jackpot when Karen tries to buy his forgiveness after she loses his pet parrot Guapo.
A deceiving, but flattering, newspaper photo gains Grace the attention of an old crush who was never one to keep abreast of her before. Meanwhile, Jack is destroyed to learn that Will had a thing with his former fling.
Grace hits the roof when her matchmaking mom visits with yet another man in tow: one of Grace's childhood friends. At first Grace is infuriated by her mom's matchmaking, but her anger soon turns to disappointment when he turns out to be a perfect match...for Will. Meanwhile, Jack and Rosario meet with an INS agent who's well acquainted with Jack's past.
With 90 percent of his practice now devoted to the wealthy Harlin Polk, Will dismisses all of his smaller clients, who believed in him before he became a success. But when Harlin's deal falls through, Will finds himself out of work. Meanwhile, Karen's husband Stan puts his foot down and tells her to quit her wild spending, and Grace steps in to help her friend master the art of living within a budget by taking her outlet shopping.
After Will closes his office, Jack challenges him to become a cater-waiter on his staff; Meanwhile, Grace finds out a dirty secret about Karen when she catches Karen at work....in an adult film.
When Will and Grace meet Jack's mother and learn that not only is she unaware that her son is gay, but she also believes that he has had a romantic relationship with Grace, they invite her to Thanksgiving dinner with Jack hoping to force the issue into the open. But nobody is prepared for the holiday surprise that she has for them.
Grace looks to Will for representation when a hotshot lawyer doesn't pay her for a consulting assignment, but he ends up making Will a job offer. Meanwhile, Jack and Karen turn a training film set into an adult entertainment experience.
Friends Rob and Ellen are feeling neglected when Will and Grace begin hanging around with a hipper, younger couple: rock 'n' roll photographer Kai and art-gallery manager Naomi. Meanwhile, Jack and Karen help each other through a parent-teacher conference for her step-kids.
When Ben tells Will that he has until Friday to find a new client or lose his job, Will kisses up to Karen to appease his new boss. Jack and Grace try to get on their favorite TV show and then get into hot water over an antique teapot.
When Will's best friend from high school asks Will to be the father of her baby, a jealous Grace tries to thwart her baby-making plans.
Will's sexy dreams about Grace land him in therapy and send her on a couch trip with his hunky shrink. Meanwhile, Jack and Karen clash over her treatment of Rosario.
Will's ideal relationship with his loving father sours when his dad prepares to accept an award at his company's dinner banquet but tries to dissuade his son from attending because he's told everyone that Will is married to Grace. Meanwhile, Karen's private detective finds Jack's biological father.
Will and Jack appear on "Today" to protest NBC for yanking a gay kiss from a sitcom episode. Meanwhile, Grace seeks Karen's advice on dumping a weirdo beau.
When Will is set up on a blind date by his boss, he has internal debates on whether or not to go. Of course, Jack gives Will advice on how to be a good blind date. Meanwhile, Grace continues to struggle with her wimpy boyfriend Josh as Karen doles out some typically un-wanted advice.
Will's former boyfriend, Michael, is back in town and may want to rekindle their relationship. Meanwhile, Karen tries taking her "career" more seriously and asks Grace for greater responsibilities.
While on a blind date, Will finds out that Karen's husband Stan has had a heart attack and rushes to the hospital to be with the gang. Will, Jack, Grace, and Rosario all speculate on who Karen will turn to for her inevitable emotional breakdown. After all, who will pay the bills if Stan dies?
After winning a call-in radio contest for prized concert tickets, Grace vows to reciprocate and volunteers her time to charity, but when she recruits Will to join her at a community center, she quickly begs off her commitment when it conflicts with her busy social calender. Meanwhile, Karen and Jack don't escape either from Grace's newfound charity which forces Karen to rifle through her closet -- and allows Jack to accidentally donate a pair of Karen's most-prized shoes.
When Rob and Ellen ask Will and Grace to be the best man and maid of honor at their wedding, Grace's sexy past with the groom is exposed when Ellen learns at her bachelorette party that Grace once slept with Rob. Meanwhile, Jack is confused by his reaction to the entertainment at Rob's bachelor party.
Grace suspects Val may have stolen her music box and tries to convince Will that their neighbor is a kleptomaniac. Meanwhile, a gay man trying to go straight tries to convert Jack into a non-practicing homosexual.
It's a scary glimpse into the future for Will and Grace when they visit their curmudgeonly retired college professor only to discover that he is a bitter old man that has a "Grace" of his own. Meanwhile, Karen must confront her most mortal enemy -- the kitchen -- when Stan requests a homecooked meal for his birthday, and she looks to Jack and Ben to come to her rescue.
Grace is thrilled when, thanks to Karen's social connections, she gets the chance to land a prestigious client for her interior-decorating firm. The only problem? She must compete with international design goddess Helena Barnes. To help boost Grace's confidence, Karen assumes the alias of "Anastasia Beaverhausen" to dig up dirt on the socialite. Meanwhile, Jack tries marketing an odd invention: a tush pad for riding the New York City subway.
Will promises not to interfere when he learns that Grace has gotten romantically involved with his boss, Ben. Meanwhile, Jack finds Rosario having an affair with Gardener, and she requests a divorce from Jack, who fears losing Karen's financial support.
Will promises not to interfere when he learns that Grace has gotten romantically involved with his boss, Ben. Meanwhile, Jack finds Rosario having an affair with Gardener, and she requests a divorce from Jack, who fears losing Karen's financial support.
Will returns from the island to find that Grace and Jack have bonded, leaving Will feeling left out. Meanwhile, Karen feels guilty when her actions lead to Rosario being arrested for smuggling.
Will and Jack's apartment becomes a haven for Grace after a break-in attempt at her place; Meanwhile, Jack and Karen still aren't speaking over the divorce debacle.
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.
Grace is appalled when an impressionable new intern suddenly emulates Karen and takes on her brass persona, causing the office to go haywire. Meanwhile, Will and Jack muck up a gay-sensitivity seminar for local cops, but the two stray from the peaceful message and get into a fight with two lesbian volunteers when the women accuse them of using sexist language.
Grace finds it hard to call it quits with Ben, whose charm makes her reconsider. Meanwhile, to save his failing cabaret act, Jack unsheathes his claws and writes nasty new material based on Will's private life.
A "Cyrano de Bergerac"-style plot has Jack borrowing Will's words to impress a crush, while an ex asks an amazed Grace to join him in a threesome with his new lover.
Will reluctantly decides to use a birthday gift certificate from Grace to consult a psychic about his future and encounters Sue, an absent-minded psychic who operates out of her messy living room and whose predictions leave him reeling. Meanwhile, pop icon Cher encounters her biggest fan: Jack; and Karen frowns on Grace's new employee at the design firm.
A crucial confession highlights Thanksgiving 1985, when college student Grace takes boyfriend Will home to meet her family, who then comes out of the closet. Also, we learn how Will and Jack became pals and how Karen ended up with hubby Stan and Rosario.
A crucial confession highlights Thanksgiving 1985, when college student Grace takes boyfriend Will home to meet her family, who then comes out of the closet. Also, we learn how Will and Jack became pals and how Karen ended up with hubby Stan and Rosario.
Will and Jack threaten to destroy their friendship when they both go after the same guy. Meanwhile, Grace meets a great new guy, but she is worried that an ugly sore on her lip will scare him away. But she is the one who winds up being scared away when she learns that the guy has six toes on one of his feet.
When they are asked to read at Joe and Larry's civil union, 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.
Will and Grace pose as millionaires interested in buying the townhouse of Sandra Bernhard. Meanwhile, Karen attends stepson Mason's swim meet; and Jack becomes obsessed with a Ricky Martin scooter and Britney Spears platform shoes on eBay.
Will finally works up the chutzpah to call Matthew, whom he met at Banana Republic. Though Will strikes out when he tries impersonating a sports fan for Matt's benefit, sparks still fly between the two. Meanwhile, Grace busies herself redecorating Jack's apartment; and Jack and Karen are convinced that Grace is a psycho.
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.
Will chides Grace for owning an old car "with no A/C and 'old-man stink'," so she lets him sell it. But when she decides she wants the lemon back for sentimental reasons, it proves difficult to retrieve from the quirky buyer, Sister Louise. Meanwhile, a cryptic postcard from his mother convinces Jack that he's half black. And when a fellow trophy spouse tries to steal Rosario, pool shark Karen challenges him to a game--with her trusty maid as the stakes.
Will's father George returns, harboring a spicy secret, in this intrigue-filled episode. As if sitting through "Seussical" on a date with a Frankenstein lookalike weren't rough enough, Grace spies George at the theater--getting very cozy with a woman who isn't Will's mother. After she spills to Will, he goes into denial, refusing to deal with this revelation. But an explosion comes anyway when George's giggly mistress is indiscreet. Meanwhile, Karen and Jack plot to nail Stan, who's also suspected of adultery.
Will's father George returns, harboring a spicy secret, in this intrigue-filled episode. As if sitting through "Seussical" on a date with a Frankenstein lookalike weren't rough enough, Grace spies George at the theater--getting very cozy with a woman who isn't Will's mother. After she spills to Will, he goes into denial, refusing to deal with this revelation. But an explosion comes anyway when George's giggly mistress is indiscreet. Meanwhile, Karen and Jack plot to nail Stan, who's also suspected of adultery.
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.
Will feels the heat from his poker-playing pals when their weekly get-together is compromised by an obnoxious Grace whose ineffective gamesmanship leaves her in debt to everyone, but she begs him for another chance -- and confides her secret weapon to regain her losses. Elsewhere, Karen gloats when she and Jack convince her equally haughty and naughty rival to be her "guinea pig" as the woman submits to experimental plastic surgery.
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.
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.
A whacked-out Grace is wracked with guilt over the death of a high school classmate whom she once tormented, so she drags Will along to the funeral -- and gets the surprise of her life -- while Will offers a sympathetic shoulder to a handsome grieving relative. Elsewhere, an ecstatic Jack asks Karen to accompany him when he is nominated for a MAC award for lower Manhattan non-transgender equity waiver gay cabaret.
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.
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.
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.
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 naïveté 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.
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.
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-fiancé'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 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.
Continuing from the season finale in the year's first new episode, a dazed Grace is rescued by a handsome Jewish doctor who pulls her up on his horse and delivers her just in time for her insemination with an impatient Will. But their new relationship as expectant parents puts a strain on Will and Grace's relationship when they agree not to date until their baby is born. Meanwhile, a restless Karen can't make up her mind about cheating on her imprisoned husband with the genteel but ardent suitor Lionel.
After stalking actor Kevin Bacon, Jack lands his dream job when the unsuspecting celebrity hires him as his personal assistant and immediately assigns him to find out who's been harassing him. Elsewhere, while Will and Grace wait for the right color to appear on their home pregnancy test, Grace is visited by a handsome doctor who makes her a tempting offer. In addition, Karen looks for a way out of her on-again, off-again relationship with the courtly and irresistible suitor Lionel.
Grace is so entranced by her budding romantic relationship with a handsome doctor that she asks an impatient Will for an extra month to re-consider her commitment to conceiving their child through artificial insemination -- resulting in verbal sparring match.
While Will and Grace are feuding, Karen and Jack hatch a wobbly plan to patch up their differences about co-parenting a baby by tricking each one into attending the same child's birthday party. After arguing over who brought the better gift, the feathers continue to fly as the best friends fuss over their conflicting agendas.
On Halloween, Grace allows her new beau Leo to drag her into the rustic fall countryside for a long and scary bike ride -- along with a reluctant Will and his newfound friend -- but she finds that she can't pretend to be the outdoorsy type just to please her man. Meanwhile, Jack coaxes Karen into attending a gay men's therapy session when she feels slight -- very slight -- pangs of marital guilt over her earlier attraction to the courtly suitor Lionel.
Mr. Stein, the long-absent senior partner of Will's firm, shows up unexpectedly to reassume command and whip the troops into shape. When Will discovers he was recently released from the looney bin, Mr. Stein begins to rely a little too much on Will's eager assistance. Meanwhile, Grace and Jack are shocked to discover that their highfalutin' pal Karen is now poorer than a church mouse -- and living in her limo.
When Grace accompanies Leo to dinner with some "friends," she doesn't realize that he's tricked her and instead introduced her to his real parents -- and she soon regrets her earlier salty dialogue and suggestive attitude. Elsewhere, Jack is again confronted by Zandra -- his gruff acting teacher -- when he tries to showcase his meager talent in a class while a willing Will joins Karen in subjecting to a Botox facial injection.
After Grace impulsively accepts a marriage proposal from Leo, there seem to be a million roadblocks between her and an actual wedding, not the least of which is her best friend Will's unease about the whole idea. Grace's pals, especially Will, are hurt that they weren't invited, but all seems forgiven when everyone--including Grace's outspoken mom and the subdued Mrs. Markus--gather days later for a swank reception. It should be a festive bash, but the emergence of unsettling details about Leo, and about the park nuptials, give Grace reason to wonder whether she has made a mistake.
After finding out that their park nuptials were invalid, Grace and Leo decide to have a large, traditional wedding. Will keeps busy planning the wedding, but after Grace asks him to give her away, he has to deal with his feelings of giving away his best friend to another man.
After a displaced Karen is booted from her Palace Hotel digs, a sympathetic Will agrees to let her move in with him -- at least until she turns his apartment into a federal disaster zone with her exorbitant lifestyle, forcing Will to try and unload her onto Grace's shoulders. Meanwhile, Jack loses style points when he poses incognito out of fear that the "Gay Mafia" has it out for him.
On Christmas Eve, Grace is torn when she has only two tickets to "The Nutcracker" musical and can't take both her best friend Will and new husband Leo -- but her back-and-forth indecision leaves Will spinning like a Hanukkah dreidel between a dithering Grace and his previous holiday plans with Jack and Karen.
When Jack convinces tangle-footed Will to join him on a gay soccer team, Will's inept play leaves him warming the bench -- which allows him to bond with teenaged Elliot who also is the last man called upon with his own youth soccer team. Meanwhile, Grace is delighted that Karen is giddy in anticipation of her date with a handsome restaurant owner.
When Karen sets Will up with her hot cousin Barry, Will finds a geeky guy with a scraggly beard and greasy hair… and he just came out. Meanwhile, Grace is puzzled over what to make of her strange bohemian neighbor when she moves into Leo's Brooklyn digs.
Will and Jack continue their campaign to adapt Karen's awkward cousin Barry to his new lifestyle -- but their flamboyant efforts to help him only remind Will of his own clumsy experiences when he came out in 1986. Elsewhere, Grace feels abandoned by Leo when he leaves for a month to offer his medical services to the needy in Africa.
Jack suffers Karen's wrath when he is seduced into friendship with her manipulative British romantic rival, who has set up house with Karen's ex-husband. Meanwhile, Will and Grace try to re-connect their lagging friendship with a competitive night of board games with their friends.
Grace has a girl's night in Brooklyn with Karen, Rosario, Ellen and new neighbor Julie -- and she offends Karen when she doesn't take her advice regarding Leo. Meanwhile, Jack reconnects with his childhood babysitter and falls back into childhood patterns, befuddling (and disturbing) Will.
Will and Jack's transformation of Karen's schlubby cousin Barry is complete -- but his coming-out at the HRC gala leaves Will with mixed emotions about his new "creation," prompting some unwanted advice from Grace. In another corner, Karen duels with her flamboyant rival Beverley Leslie in a war of wills during the silent auction.
A jealous Will keeps a wary eye on the re-modeled Barry when he spies him on a date with Jack, while Karen switches roles with Rosario pretends to be a maid in order to court a handsome maintenance worker. Meanwhile, Grace finds herself hanging out more and more in her old digs in Will's apartment as she waits for her husband to return from overseas.
Still nursing a grudge over his last failed relationship, Will forms a gin-soaked anti-romance club with other lovelorn losers -- his cuckoo boss, Mr. Stein, and Karen -- but the threesome shrinks dramatically when Stein takes a shine to the ever-ready Karen. Meanwhile, Jack sneaks a video camera into Grace's private boudoir and records her privates -- and posterior -- for posterity.
Will's attempt to orchestrate a surprise for Grace's birthday by sneaking Leo back from Africa deflates like so many birthday balloons when Leo arrives earlier than expected -- and after Grace bumps into Leo, they agree to an elaborate charade to keep Will's "surprise" intact. Meanwhile, Grace recruits Jack and Karen to keep Leo out of the way until the appointed time but they take their mission too seriously.
Prompted by a sudden urge to meet "real people," Karen finds instant karma with a peculiar yet high-maintenance office worker who happily shares many of Karen's eccentricities -- including her taste in men. Meanwhile, when Will falls off his clogs and twists an ankle, he develops a habit of taking too many painkillers, and his drastic personality change prompts a concerned Grace and Jack to intervene and interfere.
Will reluctantly opposes Karen when he represents her husband while she hires a goofy, immature young man who seems barely out of high school to argue her case -- and Will takes pity on the pseudo-slacker. Elsewhere, Grace hires Jack to temporarily replace Karen but finds she might have to choose between her friendship with him and a wealthy client who broke his heart.
In the middle of her divorce proceedings, Karen learns that ex-husband Stan has suddenly passed away, and the funeral becomes a contest of wills between Karen and her British rival -- and a free-for-all when the will is read for everyone who ever felt deserving, such as Will. Meanwhile, Grace is shocked when recently returned husband Leo is called back into service by Doctors Without Borders and asks her to make the trip with him to Guatemala.
It's anchors--and antics--aweigh in the fifth-season finale, as the gang sets sail on a yacht owned by Karen's late husband, Stanley. She's planned a Caribbean cruise to scatter at sea the ashes of her spouse. But as Jack and Will frolic, Grace frets. That's because her hubby, Leo, is keeping company with a very seductive MD while on a medical assignment in Guatemala. Karen, too, is troubled, admitting that "I don't know what I'm going to do without you, Stanley"--a sentiment echoed by a confrontational stowaway.
A half-hour clip show was shown after the 100th episode, featuring outtakes and bloopers.
A 15-minute special featuring clips of guest-star stints, dating back from 1998 to 2003. Spotlights include Kevin Bacon, Matt Damon, Michael Douglas, Cher, Demi Moore, Sandra Bernhard, Molly Shannon and Madonna. Hosted by Eric McCormack.
Will and Jack awake in a precarious position - sharing a bed in the nude - while at sea. Unable to remember every detail from the night before, the two alleged bedfellows deny the possibility that anything happened, but each grow concerned as to how to dump the other. Meanwhile, Grace's discovery of a love letter in Leo's bag from a female colleague prompts her to doubt his fidelity and Karen survives a night fighting for her life while afloat in the forbidding night sea with a freighter full of Russian sailors, and must honor a pact with savior Rosario.
When Leo invites his hip and trendy ex-girlfriend to a friendly dinner party, Grace turns to Will, Jack and Karen to round out the guest list and keep the night running smoothly. However, when Leo's ex turns out to be the only girl Will ever slept with, Grace's jealousy gets the better of her. Meanwhile, Karen discovers Lorraine's teacup poodle Chompers hiding in Stan's closet and searches for a new owner for the puppy.
When Grace and Leo join Karen for a friendly game of tennis at her exclusive club, her fierce playing style sends Grace fleeing the court. However, when the reason for her angry play is her hatred for Leo, Grace is determined to find a way for them to get along. Elsewhere, a nervous Will suckers Jack into visiting his depressed mother in Connecticut hoping they can cheer her up.
Earning a brief speaking role in an off Broadway play, Jack shares the stage with legendary actor James Earl Jones. However, when the play's director rejects James' performance in favor of Jack's one-line triumph, the award-winning actor looks to his co-star for instruction - enrolling in the McFarland acting school. Meanwhile, new roommates Will and his mother Marilyn continue their living arrangement, despite a secret desire to part ways.
Depressed over his decision to leave Doctors Without Borders, Leo turns to a motivated Will to rekindle his love for New York. However, when Will's version of "the best of New York" -- filled with long shopping trips and high tea -- doesn't do the trick, Leo decides to move in a different direction. Meanwhile, Jack teams up with his new coach Karen as they prepare for the annual gay spelling bee.
Continuing his new role as caretaker for a disabled Marilyn, a resentful Will takes his wheelchair-bound mother for an afternoon roll in the park and bumps into an attractive bachelor Tom wheeling an invalid of his own. Using his mother as a reason for a daily rendezvous in the park, Will attempts to build up the courage to ask Tom out. Elsewhere, Karen continues her lifelong quest to hunt down hubby-stealing Lorraine tracking her to a room at the Knickerbocker hotel only to discover occupant to be her father Lyle.
Pressured by her lawyer Will, Karen decides it's time for her annual Walker corporate physical, but begins to regret this decision after being examined by a slightly unorthodox physician. Elsewhere, while accompanying Karen to her physical, Jack finds his true calling -- student nursing -- and begs Will and Karen to support this new endeavor or face his eternal scorn.
When Grace returns back to New York for her mother's birthday, Will tries to coerce her into staying in town a bit longer so the two can spend some quality time together. Meanwhile, Jack struggles with his new nursing teacher, Nurse Carver so Karen threatens her into letting Jack skip class and still make the grade. But, to everyone's surprise Jack discovers that he really misses nursing school and learning.
Attempting to help Grace shake off her marital woes, a well-dressed Will asks her to accompany him on his dinner date only to be stood up by his new man. Nursing his broken heart, Will catches the eye of a female diner while Grace reunites with a man from her past with whom she shared a forgettable romantic moment in a dark bar. Meanwhile, Karen takes Jack out to celebrate his first month as a student nurse, only to cross paths with her nemesis, Emmy winner Candice Bergen -- sparking another battle in their on-going prank war.
Opting out of the annual Grace Adler Design Christmas party, ultimate "Fanilow" Will spends the night waiting in line for tickets to a special Barry Manilow concert -- only to have his weak bladder force him to make a quick pit stop and entrust Grace to hold his place. However, Will's snubbing of an overweight man in the bathroom line leaves his chances of meeting his idol in doubt. Meanwhile, a distraught Grace discovers her mother has cancelled on their annual Hanukkah shopping spree to have dinner with Jack, as Karen discovers the inspiring music of Manilow.
When Grace's rebellious, free-loading older sister Janet comes to town to launch her new jewelry enterprise/folding table subway stand, Grace decides to put her foot down casting her sibling away. However, when her tough love prompts Janet to go corporate by taking a 9-5 job and studio apartment, Grace can't seem to handle her new image. Meanwhile, Karen continues to spurn Lyle's proposals, only to have a change of heart after Lorraine stops by for an impromptu visit, to declare her disapproval over Karen's "relationship" with her father.
Attending a local gallery opening, Will catches the eye of a rich plastic surgeon, who uses his vast fortune to provide the modest lawyer with a new level of material possessions. However, when Will realizes that he has become a "lady of leisure," he decides to confront his sugar daddy/boyfriend. Meanwhile, Grace's thirst for delectable Asian noodles sends her to a new local restaurant, but an argument with the owner prompts her to launch a boycott of the establishment.
Love is in the air as Will's slightly eccentric new client falls for Jack after he interrupts their meeting, but when Jack refuses to accept the romantic offer, Will sinks to bribing him in the hopes of furthering his career. Elsewhere, Grace and Karen take a trip to Leo's cabin in Vermont in order to fix the plumbing -- and uncover a secret pile of cash in the master bed.
Will decides to further his cooking skills by taking a class and invites Jack to join him in the kitchen. However, when Jack decides to include his new boyfriend Stuart, the gourmet attorney finds himself the sad single in a cooking class full of couples. Elsewhere, Karen's mother Lois returns to town, slightly unnerving her daughter and calling on Grace's thrifty design talents to help decorate her new apartment.
Dynamic enterprisers Will and Grace begin a new business venture as they buy old apartments to refurbish and re-sell for a tidy profit. When budding student nurse Jack bumps into his former acting mentor Zandra, the pair of entrepreneurs finds their first project apartment. Meanwhile, Karen renews her romance with Lyle Finster, but the couple's bliss is interrupted by an unfortunate houseguest when Lorraine moves in.
Enjoying the success of their new business venture, entrepreneurs Will and Grace help their apartment buyers Jack and Stuart settle into their new life under one roof. However, when Grace receives a higher offer on the apartment, the "friendly flippers" attempt to break-up the happy couple by encouraging Jack's cold feet as they see a chance to make a quick buck. Meanwhile, Karen demands that Lyle finally discipline his unruly daughter Lorraine, nearly shattering the couple's budding romance.
Searching for a movie-watching pal after Stuart opts out, Jack invites Grace for an afternoon at the theatre. However, when the duo discovers Stuart and a young mystery man secretly catching a matinee, Jack is left questioning their relationship. Elsewhere, Will attempts to teach Karen the skills of driving, but the road warriors have a run in with the law their first trip behind the wheel, prompting Will to fight the ticket in traffic court.
Tip-toeing through his budding relationship, an apprehensive Will makes the mistake of taking Grace's advice on love, playing hard-to-get with his new pseudo-boyfriend. However, when his game playing causes a rift in this budding romance, Will is left questioning Grace's wisdom in matters of the heart. Meanwhile, a distraught Jack and Karen bravely attempt to soldier on after learning their favorite television shows will be going off the air.
Smitten with his new boyfriend Vince, Will puts his relationship to the test introducing him to the overly critical Grace for her approval. However, when Grace abruptly cuts the introduction short, Will is convinced of her disapproval of Vince and thus begins to question his own feelings. Meanwhile, Karen drops a bombshell on Jack, revealing that after her upcoming wedding their friendship will be forever changed, forcing him to begin casting calls for her replacement.
Responding to the pleas of his father's mistress turned girlfriend Tina, Will attempts to discover whether there is a new woman in his dad's life. However, when his father's new mistress turns out to be his mother, Will must find a way to break the shocking truth to Tina. Meanwhile, Elliot's decision to try out for his high school cheerleading squad has Jack all smiles as he is determined to help his son make the team.
On the eve of his graduation from nursing school, a nervous Jack turns to Will for help writing his commencement address. Reconnecting with his past dreams of being an accomplished playwright, Will over-analyzes the speech, searching for the life experience that sent Jack to nursing school as a source of inspiration.
Opting to forego a picturesque fall wedding and elope in Las Vegas, Karen hops a plane to "Sin City" with fiancé Lyle and faithful friends Will and Jack. Meanwhile, Leo returns from Cambodia to meet up with Grace at the wedding, but their reunion is delayed by a design emergency.
Opting to forego a picturesque fall wedding and elope in Las Vegas, Karen hops a plane to "Sin City" with fiancé Lyle and faithful friends Will and Jack. Meanwhile, Leo returns from Cambodia to meet up with Grace at the wedding, but their reunion is delayed by a design emergency.
Jack and Jennifer Lopez return from her summer tour to relax, but a pushy Karen recruits Jack to help her get J-Lo's attention for her newly written song, "FYI: I Hurt, Too." Meanwhile, Grace takes out her frustrations over her cheating husband Leo on a beat-up Will.
After Jack is fired as a backup dancer by Jennifer Lopez, she gets him an audition with Janet Jackson for her performance tour. Meanwhile, Will and Grace try to get back to business as usual and mend Grace's broken heart, only to have her come between Will & Vince.
Grace has a surprise reunion with Val as she attempts to steal doughnuts at an AA meeting. She gets hooked on AA meetings for free therapy and food and Val and Karen have a confrontation which leads to Grace's exposure as a fraud. Meanwhile, Will and Jack attend a gay television focus group, only to have Will kicked out and Jack hired as Junior VP of New Programming.
When Will and Grace meet a stranger named Ned in the elevator, Grace accuses Will of being too nice to people he doesn't know. While Grace befriends Ned and invites him to dinner, Will makes some nasty remarks about him, but they soon discover that Ned's not the best company to keep. Meanwhile, Jack is having trouble at his new company, Out TV, because he feels he can't relate to his co-workers after they mock him about his Cher doll. Karen and Rosario lend some much-needed support.
It's Will's birthday and everyone is in the mood for a happy birthday celebration, although Will is a bit hesitant because he has never had a happy birthday. Now that he is in a good relationship with his new boyfriend Vince, Will decides to give his birthday a chance. Grace runs into Vince shopping and notices that he has bought Will a key chain -- in the hopes of giving Will the key to his heart or apartment, and she tells him that Will would hate the gesture. Meanwhile, Karen is depressed because Will's birthday coincides with her late husband Stan's birthday.
Will convinces Jack to aid a local gay-bookstore owner to save his store from closing. Meanwhile, Grace's first design job after her divorce is for a young, obnoxiously-in-love newlywed couple. After a few conversations with the couple Grace decides she cannot do the job because she cannot bear being around them. Karen decides to help Grace out and completes the job for her with an uncharacteristic flourish. Grace can't bring herself to give Karen any credit for the job that Grace couldn't bear doing herself, resulting in Karen quitting her job as Grace's assistant.
When Will and Grace invite Vince and his straight female friend, Nadine, over for a meet-and-greet dinner, they find to their horror that their guests are actually polar opposites of themselves. Meanwhile, Karen is still angry with Grace and decided to leave the firm when Jack comes to her rescue and hires her to be his new assistant at 'Out TV'.
Grace comes home from a great date and listens to a staticy message she's received from Leo. She thinks Leo is telling her happy anniversary and that he wants to meet on the top of the Peninsula Hotel as they had always planned. Grace hides the message from Will, but when Will learns about it, he decides to take Grace to the Berkshires to get her mind off of Leo. Meanwhile, Karen and Jack try to set each other up. However, after Karen gets paired with her gardener and Jack is set up with a straight, married guy, Jack and Karen decide they are the best people for each other.
Will, Grace, Jack and Karen go on a road trip for Grace's get away weekend -- a weekend devoted to not mentioning the name "Leo." Jack and Karen hate the car ride and quickly decide to bail on the plan. Elsewhere, when Jack spots Peter, a "sinfully delicious" man who Jack remembers from a cocoa commercial when he was a kid, he recruits him to be the new face of "Out TV," much to the surprise of Rip Taylor who also wants the gig.
When Vince's mother injures her leg and is unable to make her traditional Italian Thanksgiving, Will comes to the rescue by offering to make his own special dinner -- but Vince's slap-happy mother refuses to give Will any credit. Meanwhile, Jack gives Vince's sister Ro a few pointers on a big secret she is keeping from her family and fiancé. Elsewhere, Grace and Karen get very cozy with Vince's much younger cousin.
When Vince's mother injures her leg and is unable to make her traditional Italian Thanksgiving, Will comes to the rescue by offering to make his own special dinner -- but Vince's slap-happy mother refuses to give Will any credit. Meanwhile, Jack gives Vince's sister Ro a few pointers on a big secret she is keeping from her family and fiancé. Elsewhere, Grace and Karen get very cozy with Vince's much younger cousin.
Grace attends a holiday party at Will's mother Marilyn's home and accidentally breaks a treasured Lladro figurine. Will convinces Grace not to tell his mother and to blame the accident on one of the other guests at the party. Elsewhere, Karen's stepdaughter, Olivia, comes to stay for the Christmas holiday and Karen pawns her off on Jack, who fits right in with the teenage girl and her friends.
Scott Woolley, an old high school classmate seeks revenge on Karen for ruining his senior year by trying to become president of Walker, Inc. After Scott prepares a presentation that wows the board of Walker, Inc., he takes over control of the company, much to Karen's dismay. Meanwhile, Jack and Grace take the day off of work to go to the movies. While at the supermarket getting snacks, they run into Vince and his co-worker and assume that Vince is cheating on Will.
Will is up for partner at his law firm. His boss, Margot, invites the candidates for partner to a dinner at her house, where she will ultimately make the final decision. Will, who is worried that Vince will ruin his chances of getting the promotion, is reluctant to bring him as his date. Grace also attends Margot's dinner party under the pretense that Margot has set her up on a blind date. Once there, Grace realizes the blind date is with Margot's husband. Elsewhere, Rosario becomes sick and Karen refuses to believe she is really ill.
Scott Woolley, under the alias Mr. Osment, hires Grace to design his new restaurant under the condition Grace fires Karen from her design firm. Grace later tells Karen about the incident and they realize the man that hired Grace is really Scott Woolley. Meanwhile, Jack takes Will out for a boys' night to get his mind off of Vince, but ends up ditching Will.
Valentine's Day is full of surprises. Grace tries to ignore the greeting card holiday but romantic urges eventually send her into the arms of the enemy -- none other than Nick, a hunky greeting card writer. In a dramatic change of events, Karen's former nemesis Scott Woolley tries to win her heart by showering her with gifts but Karen's eyes are on larger things -- her new overweight Internet date. Elsewhere, after dancing with a lesbian couple Will and Jack find comfort in each other's arms for the Valentine's Day spotlight dance.
Grace drags Will along to keep her in check during her first date with Nick only to leave a heated Will at his table for one. Meanwhile, Karen hatches a wild plan to get Jack a date with Aaron, the neighborhood bird enthusiast, only to ruffle some feathers when things don't quite go as planned.
Will agrees to fire Karen's pastry chef until the baker cooks up a delectable love triangle for the three of them. Meanwhile, Grace enlists Jack's help in launching boyfriend Nick's career as a television writer, but Jack shatters Nick's script-writing dreams.
Jack convinces Will that they need a change of scenery and should buy a vacation home in Middleborough, an up-and-coming gay community. After purchasing a new pad, the duo find out that it is not quite the gay getaway they had imagined. Instead, Jack landed the two in a blue collar town just two hours away from the newest gay hotspot. Meanwhile, Ellen asks Grace to babysit her three children, but changes her mind when she finds out Will is out of town.
When Will convinces Grace to see his therapist, Dr. Georgia Keller, he becomes increasingly jealous when the two women form an instant friendship. Grace and Will begin to compete fiercely for Georgia's attention -- and a place in her upcoming book. Meanwhile, glasses bring Karen to a whole new level of clarity.
When Grace convinces Karen to accompany her to her father Martin's birthday bash, the situation turns awkward when it is just the three of them. Struggling to gain the attention of her seemingly aloof father, Grace tags along with him to the golf range in hopes of scoring some quality bonding time. Meanwhile, Karen keeps herself entertained with Martin's buddy, Burt Wolfe. Excited about the date that Jack has arranged for him, Will discovers the true meaning of the phrase "blind date."
After a near-death experience in a jean boutique, Grace decides to write her will and enlists Will's legal expertise. To make sure she's fair when bequeathing her money, Grace visits Will's mother to find out how much Will plans to leave her and is shocked by what she finds. Thanks to Grace, Will also takes a look at his life and decides it's time to make a life altering career move. Meanwhile, Jack and Karen find an imposter teaching Jack's McFarland Method of acting.
Having quit his job at the law firm, Will turns to a career in writing where he catches the eye of Malcolm, who claims to have high-profile connections -- but when his writing career fails, Malcolm has another job offer for Will. Meanwhile, Tom, an old flame from college, returns to ask Grace to design a hotel that he and his wife just bought -- only to discover that there are still romantic feelings between the two of them. Jack struggles to produce his latest show for Out TV, but spoiled child star Randall fails to embody Jack's vision. Under threat of a lawsuit, Karen is forced to publicly apologize to Beverley Leslie for an embarrassing rumor.
After his first day, Will becomes suspicious of his new job -- especially when he finds himself in an empty office with no co-workers, a German shepherd and a Russian-speaking thug. When Will confronts his new boss Malcolm, he discovers a startling secret about an old friend. Meanwhile, Grace quits the hotel design job when Tom can no longer hide his feelings for her. At OutTV, Jack has been promoted to host of his own show, "Jack Talk," and is reveling in his newfound celebrity until the network tells him to split the spotlight with his new co-host -- Karen.
The eighth-season opener, broadcast live twice, centers on Karen, who's unaware that her presumed-dead spouse--the never seen Stan--is actually alive. Her friends are reluctant to tell her because she's now involved with the enigmatic Malcolm
Will suspects that Karen is more upset about Stanley being alive than she's actually letting on. Grace becomes the target of rage from gay men all over New York when her comments on Jack's talk show are misconstrued during editing.
When Jack learns that Will never learned to swim, Jack insists that he teach Will how. Karen sets Grace up on a blind date with one of Malcolms friends, but Grace can't stand him or his penchant for bad poetry during their never-ending nine-course dinner.
Karen is finally forced to come to terms with her feelings for her presumed-dead husband when Jack surprisingly tells her he thinks she belongs with Stanley, not Malcolm. Karen is adamant that she will never forgive Stan and wants nothing to do with him--until Malcolm informs her that Stan has given her to him without a fight. Meanwhile, the new, charitable Will begins doting on the elderly Clyde and invites him to the Tenth Anniversary Game Night Spectacular, much to Grace's dislike. He is worried that he will end up like Clyde one day--a lonely old gay, but it turns out that the old man and Will don't have as much in common as originally thought.
The day before Will's charity auction and carnival, Jack meets and begins dating Baby Glenn, who is still riding his fifteen minutes of fame from when he got trapped in a hole for three days in the eighties. The two "celebrities" agree to be auctioned off for charity -- Baby Glenn's fans spend over a thousand dollars, but Jack begins to question his own notoriety when no one bids on him. Meanwhile, Karen just can't force herself to break up with Malcolm, so to soften the blow she recruits Grace to be his date to the carnival. But Grace can't stand his weird quirks and clingy personality and finally makes Karen confront him.
While en route to London for the weekend, Will and Grace spot Grace's ex-husband Leo on their flight. Will charms a pair of gay flight attendants, who also happen to be dating, so he can smuggle Grace into first class to talk to Leo. Back in New York, Jack tries to reunite Karen and Rosario, but this proves difficult when their stubbornness outweighs his good intentions. Also complicating matters is Karen's new manipulative maid Leni, who is not anxious to give up her comfortable new job.
When Jack decides on a whim to move, Will is excited at the thought of helping him look for a place. After becoming involved in a cause to save two gay penguins from being separated at the zoo, Will starts to think closely about his dear friendship with Jack and what it would mean if he no longer lived next door. Meanwhile, during an afternoon of shopping, Karen and Grace bump into pretentious socialite Beverley Leslie, who invites the two ladies to attend his recently deceased wife's memorial "celebration." When Grace decides to try on one of the dead wife's rare dresses before the ceremony, she experiences a "wardrobe malfunction," which she must try to conceal.
Grace finds it impossible to put up with her mother Bobbi's constant nitpicking, so Jack takes it upon himself to help her because, according to him, no one knows how to be a good daughter better than a gay son. Jack subjects her to a barrage of Bobbi-esque insults until Grace finally learns what her mother really means underneath her harsh words. Meanwhile, Will's first case at the Coalition for Justice is about tenants' rights, and the slumlord turns out to be none other than Karen.
While spending the holidays at Will's mother Marilyn's house, Grace gets cozy with Will's brother and old flame Sam. Sam's adopted daughter finds a fan in Karen, who is intrigued by the little girl. Meanwhile, Jack helps Will's clearly gay ten-year-old nephew organize and perform a Christmas show, which Marilyn is thrilled about. Will is silently fuming, however, as Marilyn is much more tolerant of the young boy than she ever was of her own son.
The "Sound of Music Sing-Along" has come to town and no one is more excited than Grace. She plans for her and Will to attend the musical in character-like style by dressing up in costumes. However, her presumed-to-be fun night turns into a disaster when she ends up babysitting a group of children and Will accidentally goes to the wrong theater becoming further detained by James, a handsome man he meets. Meanwhile, Karen and Jack try to flee when she gets in trouble with the theater's manager, who blocks off the exits, trapping everyone inside and forcing them to plot their escape.
All of New York's high society has been invited to Karen's birthday party - but the affair goes downhill when Will, Grace and Jack embarrass themselves and wind up crammed together in Karen's bathroom with the birthday girl.
Grace is concerned and confused when Will so adamantly insists that she turn down her job offer from his former boss Margot, who has asked Grace to redecorate the law firm. When she takes the job after telling Will that she wouldn't, Grace learns some startling news that he has been hiding from her. Meanwhile, Jack discovers Karen's softer side when he finally sees what's inside the "forbidden room" at the Walker mansion.
Will and Grace dread a dinner date with married friends Rob and Ellen who likely called the meeting to announce Ellen is pregnant yet again, but when the couple reveals that they are separated and loving it, Grace gets depressed She's quickly distracted however when Will's cop ex-boyfriend, Vince pproaches their table as their server Ignoring Rob and Ellen's big news, Will and Grace discuss how Vince must have gone off the deep end and quit the force after splitting with Will, and Vince's request to switch table assignments seems to confirm their thoughts Elsewhere, Jack decides he needs to spice up "JackTalk" by pulling an Oprah and helping his fan, Tommy Shields, come out of the closet Jack and Karen setup a bowling alley meeting with Tommy when Karen is recruited to join a woman's league game as an emergency fill-in .
Will, Karen, and a star-struck Grace travel to Los Angeles to support Jack as he accompanies Elliot to tour the UCLA campus. Coincidently, Will runs into James while in LA, but to his surprise James is Canadian and in jeopardy of being deported. After spending a perfect weekend together, Will and James find that they don't have to say good-bye to each other again when Grace makes a special proposal.
The big day has finally arrived as Grace and James get ready for their green-card wedding. To Grace's dismay, Karen takes it upon herself to ignore her wish for a low-key wedding ceremony and decides to arrange a huge affair instead including hiring the legendary Hall & Oates singing duo to perform "Maneater" at the ceremony. As the ceremony gets underway, it seems that Grace's body begins to have an unusual reaction leaving James' U.S. citizenship in jeopardy.
A nervous but optimistic Grace decides it's finally time to tell Leo she is pregnant with his child, but when she finally works up enough courage to actually meet her ex-husband she receives some unexpected news Meanwhile, Will is settling in comfortably with James until he reveals a side of himself unknown to Will And as Jack attempts to document every moment of Grace's pregnancy for his talk show, Karen sulks alone, jealous over the good fortunes of her friends.
An ecstatic Jack coerces Will into coming out with him to a gay cowboy bar to meet his new boyfriend Travis. Will soon discovers that Travis is not as perfect as he seems and steps up to defend Jack's honor, which eventually leads to a raucous event - a bar fight.
After a large corporation takes over OutTV, Jack's talk show "JackTalk" is completely revamped. An immediate change comes when the new conservative owners hire Amber-Louise as "JackTalk's" new co-host. While Jack is deciding whether or not he'll stand up to his new bosses. Meanwhilea, after seeing Grace so happy about her pregnancy, Karen decides she wants a baby of her own and offers to pay a make-up lady, Cricket, to carry one for her.
After losing his job as the host of "JackTalk," Jack vows never to return to acting. An unrelenting Karen, however, will not let Jack give up on his passion and decides to do whatever it takes to get Jack to an audition. Meanwhile, Grace accompanies Will to dinner at his parents' home, but a simple dinner soon turns into a showdown between Will and his father when his dad decides to give Grace's unborn child Will's cherished baby blanket.
Friends and family gather for the funeral of Will's father. During the reception everyone shares with Will fond last memories of his father, while Will's last memory of his father is not as pleasant. As he tries to come to terms with their last fight, Marilyn helps him realize the changes he must make in his life. Will's ex-boyfriend Vince also attends the funeral service. Meanwhile, Grace attempts to comfort the grieving younger members of the family and begins to doubt her ability to be a good mother.
Will and Grace begin attending childbirth classes in preparation for the baby, but as Will and Vince take another chance at their relationship together, Grace starts to doubt whether Will is up for raising a child with her. Meanwhile, Karen looks to Jack for comfort as her marriage with Stan hits a bumpy road but finds that Jack is a little preoccupied with his new television show.
Just as Will and Grace are settling into the idea of raising the baby together, Will's boyfriend Vince surprises him with an announcement that will ultimately lead Will to choose between his commitment to Grace and his relationship with Vince. Meanwhile, Karen shocks everyone when she announces that she has a sister, Gin, who was injured as a child during a game of Twister. Jack, on the other hand, is comforted by a man after a devastating discovery when his new show "The Badge" premieres.
The Emmy Award-winning comedy series’ cast looks back at its eight seasons of outrageous storylines in this hour-long compilation of memorable scenes and all new interviews with the cast and crew. Also featured are the series’ show-stopping guest stars who will talk about their time on “Will & Grace” and give you a glimpse into why this show has been so successful.
The culmination of eight seasons’ ends tonight with a one-hour series finale - will Will and Grace raise a child together and find ultimate happiness? Will Jack find anyone that loves him as much as he loves himself? Will Karen find true happiness with the absence of Stan? All these questions and more will be answered as this groundbreaking series concludes eight amazing seasons.
The culmination of eight seasons’ ends tonight with a one-hour series finale - will Will and Grace raise a child together and find ultimate happiness? Will Jack find anyone that loves him as much as he loves himself? Will Karen find true happiness with the absence of Stan? All these questions and more will be answered as this groundbreaking series concludes eight amazing seasons.