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When Grace receives an unexpected marriage proposal from her boyfriend, Will tries to be supportive of her decision but finally tells her that she's making a mistake, even though he's putting their friendship at risk. The situation is complicated by interference from Grace's socialite assistant, Karen, and Will's outrageous friend, Jack.
Will must decide whether to support Grace's independence by encouraging her to take an apartment across town or selfishly keep her close by inviting her to share his living space. The decision may be made easier, however, by the nagging presence of Will's current roommate, Jack, and his parrot, Guapo. Meanwhile, Karen and Jack meet for the first time and find each other to be fabulous.
When Grace moves in with Will, she complains that the guest bathroom is too small and suggests knocking the common wall down to create one big master bathroom, which results in Will having to confront his own issues on change and his ability to have a successful relationship. Meanwhile, Jack and Karen bear the brunt of Will and Grace's displaced anger.
When Grace decorates Harlin's apartment, she gets carried away with a cowboy theme. Will is both shocked and embarrassed by the cowboy chic and makes an even greater mess of the situation. Meanwhile, Jack decides to embark on a singing career with a little help from 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 Jack reveals to Grace that Will once had an affair with a "client," she becomes paranoid that Will is keeping secrets from her. Her suspicions continue to grow when Will meets Karen for a discreet meeting to discuss her legal problems and will only tell Grace he's meeting with a client.
Grace blames her relationship with Will as the reason for her lack of interest in dating and decides they can no longer have fun together. Meanwhile, Jack enlists Will's help when the IRS catches up with him.
Grace has the opportunity to buy the studio that serves as her office space and turns to Will for first-time buyer advice. However, Will's negotiating tactics lead Grace to believe that Will thinks she is incapable of closing the deal and she sets out to prove him wrong. Meanwhile, Jack wants to become a massage therapist and practices his technique on a delighted Karen.
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.
Will and Grace become hooked on a real-life soap opera unfolding in their neighbors' apartment when they begin eavesdropping through the new heating vent in their floor. As Will and Grace live vicariously through the marital infidelities of the downstairs couple, Jack feels neglected and enlists Karen's help in staging a play that drives the message home to his two best friends.
It's Will's birthday and all he wants is a nice, quiet dinner with his two best friends, Grace and Jack. When Jack and Grace discover they share a passion for figure skating, they surprise Will with tickets for Champions on Ice and Karen reluctantly joins the special evening.
Will hires a cleaning lady to "rescue" his designing roommate Grace from the creative chaos that litters their apartment, and while preparing for an annual decorators' contest, Grace develops a dependency on her maid and can't create without her. Meanwhile, Jack poses as an attorney in Will's office to impress an attractive guy he hopes to date.
Grace's visiting mom, Bobbi Adler, a would-be star whose propensity for breaking out into show tunes and impressions dismays her daughter and delights Will, Jack and Karen 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, Grace realizes she's more of a chip off the old block than she imagined.
A "surprise" birthday party for Jack astounds Will when his estranged older brother Sam turns up at the fete at Grace's invitation. Not only do sparks fly between the brothers, but electricity of a different sort crackles between Grace and Sam. Meanwhile, Karen flashes her platinum card for Jack as the pair shop until they drop at a boutique where the snooty salesmen previously had snubbed Jack.
A wary Grace tells Will of her romance with his brother, Sam, and unleashes an avalanche of resentment. While Will wrestles with sibling rivalry, Karen helps Jack come to grips with turning 30 by hiring him as her personal assistant and leads Grace to sort through her true feelings for the Trumans.
Stunned to find they have a 'date' with the same guy, Will and Grace compete for the affections of a handsome, charming new neighbor at dinner, and even Jack's finely-tuned gaydar can't pick up his preference. Meanwhile, Karen contemplates firing her driver and in a twist of irony asks Grace to role-play firing an incompetent employee.
The gang retreats to a cabin in Vermont for the weekend, where Grace rekindles romance with an old flame and tries to hide the fling from Will, who's pining on the eve of his would-be anniversary. Meanwhile, Karen's culinary efforts go up in smoke, as does Jack's attempt to cheer Will by dragging him to a gay pub, where the town barber-turned-hair stylist sidles up to him.
Will finds a "substitute Grace" in Val, a new neighbor who is available for plans with Will while Grace is consumed with work. As Will and Val continue to spend more time together, Grace fears that she has been replaced and fights with Val to regain Will's attention. Meanwhile, Jack seeks support from Karen after the court finds him guilty of slapping a meter maid and sentences him to pick up trash.
Will invites Jack to his gym on a "buddy pass," but when he expresses his embarrassment to Grace over his buddy's gay behavior, Jack overhears the comments and looks to set him straight about prejudice. Meanwhile, Grace continues to lend her ear when Karen's marriage hits rocky ground and she and Karen share an evening of girl talk.
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, after learning how to administer CPR from Jack, Karen saves a workman's life.
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.
Despite her moving out (to across the hall), Will still feels that Grace clings to him, so she asserts her independence by having a dinner party without him. Meanwhile, to keep the INS at bay, Jack is forced to move in with Rosario.
When Grace feels that Will is abusing his power as president of the tenant's association, she runs against him. Karen tries to buy back Jack's forgiveness when she lets his beloved bird, Guapo, fly out the window.
A deceiving, but flattering, newspaper photo makes Grace look more "endowed" than she really is and gains her the attention of a former high school heartthrob who was never one to keep abreast of her before. Jack is destroyed to learn that Will had a fling with Walter, Jack's ex-boyfriend.
Grace is jealous when her mother stops match making for her, and instead sets Will up. Jack must convince an INS agent (who he dated once) that he and Rosario are happily married.
When his work for Harlin takes up all his time, Will drops all his other legal clients; a decision that later comes up to bite. Meanwhile Grace tries to teach Karen how to live on a budget.
An unemployed Will agrees to serve as one of Jack's cater-waiters, until he learns that he'll be catering for American Bar Association. Grace discovers Karen's darkest secret: she once made a porn video.
Will and Grace are shocked to learn that Jack never told his mother he was gay and encourage him to open up to her at Thanksgiving. The evening brings a revelation for Jack as well: his father isn't who he thinks it is.
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.
Tired of Rob and Ellen's low-rent taste in dining, Will and Grace start hanging with a pair of hip downtowners they meet at a sushi joint. But as the new pals paint the town, Rob and Ellen see red when they catch their best friends lying to avoid plans to dine at their favorite eatery: a coupon-crazy Italian chain in Secaucus. Meanwhile, Jack's inner child gets a little pick-me-up when he joins Karen at a PTA meeting at her kid's school.
When they appear on their favorite TV show, Antiques on the Road, Grace can't wait to dress down the guests who are ever hopeful that their tchotchkes are worth a fortune, while Jack just wants to undress the show's attractive appraiser, Porcelain Paul. But then it's all business when they realize that their junky, thrift-store teapot is actually valued at $30,000. Meanwhile, Will's new boss makes the reluctant lawyer kiss up to Karen in hopes of landing her hubby as a client.
Grace is excited to meet Will's best friend from high school until she learns that the woman has made a request: to be implanted with Will's sperm. Now Grace has to confront Will about Will being her "backup."
Erotic dreams about Grace send Will to a therapist, who seems more interested in Grace. 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 cutting a gay kiss out of an eagerly-waited sitcom episode. Will is frustrated with Jack on how much he wanted to see that kiss and kisses him. Elsewhere, Grace confides in Karen about dumping her boyfriend.
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 thinks that he has another chance with Michael, his old boyfriend and Grace's new client. 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 concert tickets from a radio contest, Grace vows to get more involved and she volunteers herself and Will to help out at the community center. Unfortunately, her charitable work conficts with the concert. Meanwhile, while collecting clothes to give to the mission, Jack donates 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.
Despite their history, Grace spends a fun evening with Val [ from ep. # 18 Grace, Replaced] only to have Will suspect her of stealing. Meanwhile Jack becomes attracted to the leader of Welcome Home-an organization for gays who have converted to going straight, so he acts straight to woo the man.
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.
To help make peace between Grace and Ben, Will has them both over to dinner, only to have their relationship go beyond friendship. But then Will finds out that Ben is dating someone else. Meanwhile Jack catches Rosario in a clinch with a lover and learns that she wants a divorce.
Forced by his boss to betray both of his friends, Will quits--only to discover that everything isn't as it seems. Frustrated, he leaves a lost Jack and Grace behind and ends up on a tropical island without a care in the world. Until Ben shows up.
After three months on the island, Will finally returns only to learn that Jack and Grace have bonded in his absence. Meanwhile Grace still can't decide between Josh and Ben; When Karen tries to smuggle pearls in the States, Rosario ends up taking the rap.
Terrified after someone breaks into her apartment, Grace stays with Will. Unfortunately, having both her and Jack under one roof is driving Will crazy and he forces them to choose which one will move out; Jack and Karen are still at odds over his divorce from Rosario.
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's delight in having a bright intern whom she can mentor turns into horror when the young woman re-makes herself into the spitting image of sassy, brassy Karen -- and that's at least one too many Karens to handle. Meanwhile, Will and Jack volunteer to act out scenes for a gay sensitivity seminar for the local police but the peaceful intent is lost when they tussle with two lesbian cast members who strongly object to their non-inclusive, sexist language.
Grace has made up her mind to break up with Ben because she's convinced their relationship is going nowhere -- but his charm and refusal to call it quits tempt her to reconsider. Meanwhile, Jack's latest and most outrageous cabaret gig is an absolute bomb until he frantically works an unwilling Will into the act by mercilessly ridiculing his attending friend's most-private confessions.
Grace rejects an ex-boyfriend's suggestion that she participate with him and his girlfriend in a romantic escapade but when she confides in Will and Karen -- who fall down laughing at the prospect -- the conservative Grace considers throwing caution to the wind. Meanwhile, Will tries to help a newly employed Jack meet a customer at a clothing store by prompting him with witty lines like a latter-day Cyrano de Bergerac.
Will reluctantly decides to use a birthday gift certificate from Grace to consult a psychic about his future and encounters an absent-minded fortune teller whose frighteningly personal predictions leave him reeling. Elsewhere, a guilt-ridden Grace hires a lackadaisical waiter whom she helped to get fired while Jack, who forever idolizes music, TV and film legend Cher, stumbles onto the real deal and meets the Oscar winner herself -- whom he mistakes for a drag queen.
In a flashback to Thanksgiving 1985, coed Grace invites her college boyfriend Will home to meet her family, but their romantic relationship swerves dramatically when a conflicted Will phones a teenaged Jack for some crucial advice. Unfortunately, Will and an angry Grace end up temporarily estranged when he blurts out the truth and she orders him out of the house -- and her life.
In a flashback to Thanksgiving 1985, coed Grace invites her college boyfriend Will home to meet her family, but their romantic relationship swerves dramatically when a conflicted Will phones a teenaged Jack for some crucial advice. Unfortunately, Will and an angry Grace end up temporarily estranged when he blurts out the truth and she orders him out of the house -- and her life.
Just as Grace seems to be on the verge of a promising relationship, she undergoes a minor medical procedure that leaves her with an embarrassing ugly sore on her lip, but even though her new beau accepts her temporary blight, she cannot return the favor when she is horrified to learn he has six toes on one foot. Meanwhile, Will vies with Jack for the attentions of the same man until each agrees to walk away to preserve their friendship.
When they are asked to read at the civil union of two friends, Will and Grace verbally spar over her self-serving, get-and-take attitude where Will is responsible for everything -- but what's really bugging him is the overwhelming feeling that Grace is behaving more like a wife than an old friend. Meanwhile, Karen tries to help a caffeine-addicted Jack get over a failed crush but he's so jacked-up on java that only a tough-love approach will work.
Will and Grace get carried away in an escrow undertow when they pose as a wealthy couple shopping for homes of the rich-and-famous and visit Sandra Bernhard's posh townhouse where they become fast friends and make an fake offer -- but their ploy fizzles when she accepts their offer. Elsewhere, Karen is forced to attend her young stepson's swim meet and is uncharacteristically chastised by another mother for arriving late while Jack begins attending Co-dependents Anonymous meetings.
A sports-challenged Will tries to impress his new friend Matt a sportscaster with his athletic skills by checking into a batting cage but it takes Grace to show him how to improve his swing. Meanwhile, Grace is given a mission: impossible when Jack and Karen ask her to exotically re-decorate Jack's apartment.
Will 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.
Grace dispatches Will to sell her dearly departed uncle's jalopy but after he makes the sale to an enterprising nun, a guilty Grace changes her mind and wants to buy it back -- but the sister makes it clear that, short of a miracle, it's going to cost her plenty. Elsewhere, Karen must duel with an equally eccentric rich friend for the housecleaning services of Rosario while Jack suddenly sees the world differently when he believes his missing father is African-American.
Grace is apoplectic when she catches Will's philandering father on the arm of a glamorous stranger, but she gets even more worked up when she tells Will -- and he's happy living with denial. Speaking of cheaters, Karen misunderstands Grace and suddenly suspects that her husband Stan is having an affair, so she sets out to even the score.
Grace is apoplectic when she catches Will's philandering father on the arm of a glamorous stranger, but she gets even more worked up when she tells Will -- and he's happy living with denial. Speaking of cheaters, Karen misunderstands Grace and suddenly suspects that her husband Stan is having an affair, so she sets out to even the score.
Grace is smitten when she meets Sumner, Karen's charming and handsome nephew, but Grace's attempts to arrange a date are constantly thwarted when Karen conjures up a litany of lies to dissuade her. Meanwhile, Will tries to terminate his dead-end relationship with a needy nebbish, but postpones the dramatic moment because he's so infatuated with the guy's lovable doggie, Pepper.
Grace's lousy poker playing leads Will's friends to ban her from the game, but Grace makes an amazing turnaround to stay in; Karen uses a snippy socialite as a guinea pig for cosmetic surgery.
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.
When Grace learns that an old school mate who she made fun of has died, guilt makes her attend the funeral. Meanwhile, Jack is nominated for a gay cabaret award.
Grace 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 Elliot 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 attorneyand when he resumes his evil childhood harassment, Will is tempted to turn to Nathan for advice. Meanwhile, Grace feels shamed when she gives Nathan a gift that is dwarfed by one from Karen: mindful of his motorcycle enthusiasm, Grace got him a rare first edition of "Zen and the Art of Motorcycle Maintenance," but Karen got him an actual motorcycle.
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 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, and Grace is so moved to help her worried friend that she moves right into Karen's deluxe apartment in the skywhere 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 Willwhile mindful of Will's fantasy of modeling in the store's catalogueand 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 proposaland when she realizes her mistake, she returns the favor, but doesn't get the response she hoped she 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.
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.
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 moneyeven 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 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 placedespite the efforts of Sandra Bernhardbut 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. (Part 2 of 2)
An excited Will presents his newly reconciled parents with a romantic cruise on their anniversarybut his idealistic plans are scuttled when he learns that each is hiding a secret. Meanwhile, due to Karen's phobia about elevators, 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 for 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 Connecticutbut 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 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; 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 meansall 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.
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.
A bicycling adventure tests Will and Grace up in the Catskills with Leo and his pal in a quest for Halloween pumpkins.
Gene Wilder plays Mr. Stein, the long-absent senior partner of Will's firm, who shows up unexpectedly to reassume command. He just might succeed if he weren't such a frantic, neurotic mess. What he needs is a smart, attentive lieutenant who can make decisions and do some of the dirty work (like firing people). Enter Will. 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.
Grace and Leo impetuously take their vows at a Central Park wedding that is a ratings stunt hosted by Today's Katie Couric. Grace's pals, especially Will, are hurt that they weren't invited, but all seems forgiven when everyoneincluding Grace's outspoken mom and the subdued Mrs. Marcusgather days later for a swank reception. It should be a festive bash, but the emergence of unsettling details about Leoand about the park nuptialsgive Grace reason to wonder whether she has made a mistake.
After realizing that she truly loves Leo, Grace decides to do the marraige thing right with a traditional wedding with a licensed judge. Will is becoming more upset over losing his best friend; however, Grace assures him that no matter what, she will always be in his life. At the wedding, Will is chosen to give Grace away after her father throws his back out.
It's Christmastime. Will is the first one in line for Barry Manilow concert, to the disappointment of the girl who arrives second. Turns out that they know each other through a Barry Manilow chat site. Grace happens to walk by and takes Will's place in the line while he goes to relieve himself. Then Grace spots her mother across the street, having dinner with Jack, even though she had said to Grace she wasn't coming to town. So, to find out what's going on, Grace calls Karen to take her place in line. Meanwhile, Will finds out that waiting in line for bathroom may ...
Lorraine's father, Lyle returns and tries to woo Karen but she rebuffs him. But changes her tune when Lorraine tells her to keep away from him. And Grace's sister who's a loafer comes to town to try out her new scheme. And when Grace tells her she's a loser and she turns things around and gets a job at a corporation which has Grace in awe.
Will succeeds where Jack fails: he becomes a boy-toy for a wealthy elder man. Grace drops a plate of hot noodles at a restaurant and declares war on them when they refuse to give her a replacement on the house.
Leo has a cabin in Vermont and his neighbor has called Grace to tell that the pipes have frozen and they need to be taken care of. Will is meeting a new, gay, client and can't go. Jack is going to see "The Boy from Oz", dying to see "Hugh Jackman ...and his huge ackman". So Grace has no choice but to take Karen with her. While they are on their way, Will meets the new client, who is a huge Lord of the Rings fan. After Jack has interrupted the meeting, the client declares, "I want him to be the lord of my ring"... In Vermont, Grace & Karen find something unexpected.
Jack is taking part in a cooking class because now that he has a boyfriend, he wants to offer him home-made food. Will goes too - and finds out that Jack brought Stuart with him. Not only is Will left cooking alone, he finds out that he is the only one who's single. Karen's mother has moved into town and is in need of a decorator - a lucky job opportunity for Grace.
Will and Grace who are now flippers (buying houses cheap and then fixing them up and selling them at a huge profit) are trying to get a house. But they learn that they have just encroached into the area of a couple of flippers known as Deirdre and Monet who are lesbians. They approach Will and Grace and tell them to stay out of their territory. Will decides to fight back by driving a wedge between them. However things don't go as planned. And Karen feeling as if she's cheating on Stan with her relationship with Lyle decides to contact him through psychic John Edward. ...
Karen enlists Will to teach her how to drive. And of course she gets pulled over by a police for speeding. Meanwhile, Grace and Jack are at movies. They see Stuart in the theater with another man and Jack starts suspecting Stuart is cheating on him.
Karen and Jack are facing a problem: not only has Sex and the City ended, but Frasier and Friends are ending too - what are they going to start following? Will dates a cop and makes the mistake of listening to Grace's dating advice.
Will and Vince's relationship is put to *the* test - will Grace approve Vince? Meanwhile, while giving Karen dance lessons, Jack realizes that their relationship is most likely to change drastically when Karen gets married.
Elliott announces that he's going to apply into the school cheerleaders, which makes Jack very proud of him. Tina confides in Will that she suspects Will's dad is seeing another woman since he is now always too tired to have sex with her. Will has to go to see his father to find out what's the truth but he isn't prepared for the truth.
Jack is graduating from nursing school and because he was voted The Most Popular, he gets to make a speech - but then he realizes the graduation day is sooner than he thought and he needs to write his speech very very quickly. Enter Will to do it for him - a potential disaster.
Karen and Lyle are "eloping" to Las Vegas on a private plane because Lyle said "screw it" to a 3,000 people wedding. Jack and Will are tagging along. Leo is coming from Cambodia, but where's Grace?
At Lyle and Karen's wedding reception, Will confronts Leo, who is experiencing strong guilt about his actions. Lyle's brother also suddenly remembers he had something to tell to Lyle. And Karen has a surprise in store for everyone.
After breaking up with Leo, Grace tries to cope with her grief by taking all of Leo's stuff out of his apartment. After Leo shows up at Will's apartment to excuse and win Grace back, she seems to finally end their relationship. Karen writes a song, which she shows to Jack. She asks him to show it to Jennifer Lopez of whom Jack thinks she is his new best friend.
Jack prepares himself for his performance as a back-up dancer for Janet Jackson. During rehearsal Janet decides that she doesn't want 6 but only 5 dancers. This leads to a dance-off between Jack and another dancer, Artemis. It turns out that Artemis is Karen's former lover. Since she still has feelings for Artemis, Karen asks Jack to let Artemis win the dance-off. Grace still has to deal with the break-up with Leo and it takes all of Will's support to make her feel better. Will is so entangled by Grace that he almost forgets about his boyfriend Vince and that he got ...
When Grace accidentally walks into an Anonymous Alcoholics meeting she meets Val again. Grace is forced to participate in the meeting. As time goes by, Grace starts to like the meetings and thinks that they are just like therapy, but just cheaper. Karen fears she is losing Grace as friend to non-alcoholics beliefs. During a test screening for a gay network, Jack has many ideas. This annoys Will, who actually has got to say a lot about gay TV-shows, too and feels out-staged by Jack.
Jack feels misplaced in the TV staff of the gay network as he feels everyone is smarter and more educated than him. He feels as if he has to adapt to his co-workers, but this change would force him to change some things about his personality and to hate things he actually likes. When Will talks to someone living in the apartment house, Grace tells him not to do so since the person could be dangerous. When Grace meets the stranger in the elevator she invites him over to have some cocktails. As it turns out, the stranger is not dangerous, but a bit weird and boring.
It's Will's birthday and Vince wants to give him the key to his apartment as a gift. Grace thinks it is not a good and a rather cheap idea and convinces him to give Will a wallet instead. When Grace then tells Will at his party what Vince original present was, he is surprisingly excited and considers it to be very romantic. Will is of course very disappointed when Vince's present is not a key but a wallet. Grace is not brave enough to tell Will that she was the one who talked Vince out of the idea with the key. Karen is very upset since Will's birthday would also have...
Grace takes on her first job after the end of her marriage. What seems problematic about the job is that the clients are Newlyweds who just got back from their honeymoon. Grace is annoyed by all their flirting and their love for each other. When Grace leaves, Karen takes over Grace's job in the clients' apartment. Will takes Jack to a gay bookstore, which is about to be closed. Will finds out that the bookstore will become a gym after it is closed down.
Will and Grace meet Vince's close friend Nadine, who is "Vince's Grace". Vince and Nadine seem to be far nicer with each other than Grace and Will, which upsets Will. He wishes Grace was as supportive for him than Nadine is for Vince. When being forced to tell what she doesn't like about Vince, Nadine reveals that she hates Will. After quitting the job as Grace's assistant, Karen works as an assistant for Jack. But, rather than working, Karen and Jack only make nonsense, which forces Jack to fire Karen.
Grace decides to start dating again after her divorce. On her first date, she meets with a guy, who Will recommended to her. Although Will is worried that Grace ruins the date, it actually goes quite well and when Grace gets home there is a message on the answering machine from her date that he liked it and that he wants her to call back. The moment Grace wants to call back she hears another message on the machine, but this time it's from Leo. He reminds her of the fact that their anniversary is coming up. From that moment on, Grace is no longer interested in her date...
After taking Grace out of town to forget about Leo and their anniversary, Will and Grace stay at a hotel and Will hopes that Grace will finally find some peace. But, Will finds out that Grace has brought the answering machine with Leo's message on it with her and forces her to get rid of it so she stops thinking about going to the roof of Peninsula Hotel to meet Leo or not. Jack has to make up an idea for a promo for Out TV and meets the perfect actor for it in a hotel where he is working as a Bell Boy. Also, other people at the network think the actor is perfect, but...
It's Thanksgiving time and Will is about to meet Vince's family for the first time. Vince's mother apparently doesn't like any of Vince's boyfriend even if she hasn't met them yet. So, Will decides to take her out on a shopping trip. During the trip Vince's mother breaks her toe, because Will told her to put on high heels and "work it". So, Will takes over the cooking job for Vince's family and his friends and everyone gathers for a nice dinner. Grace has crazy sex dreams, which leads her to the conclusion that she needs sex in real-life and sees a chance to get what ...
When Jack tell Will that Ro wants to come out of the closet and tell her family that she is a lesbian, he is about to freak out and tries to convince Ro not to come out tonight. Vince is still struggling with his suppressed anger for his dad, although he seems to do nothing that could upset his son. Grace and Karen both make out with Vince's cousin Sal and from then on compete for his affection. Annette keeps teasing Will, because of her injury, which he caused. Under all these circumstances, dinner seems to get a little messed up.
Karen's step-daughter Olivia visits her for Christmas, but Karen wants to get rid of her as quickly as possible so she makes Jack take care of her. Other than expected, Jack has a lot of fun with Olivia and Karen suddenly wants to hang out with them. Grace starts to get along with Will's mother pretty well until she ruins her favorite figuring. But since Marilyn doesn't know about it neither Will nor Grace tell her about it. The guilt over not telling Marilyn drives Grace nuts.
Karen is interviewed for parade magazine. The interviewee turns out to be an old schoolmate of Karen, who has some bad memories of her. Grace and Jack want to go to the movies and make a quick stop at a store where they see Vince. Jack feels insulted since he asked Vince to come along them. It turns out that Vince got fired from his job as a cop and works in the store. A fact which he has to tell Will yet. Grace wants to confront Vince about lying, but then backs out.
Vince finally tells Will that he got fired. While Vince basically spends all of his time hanging around at Will and Grace's apartment, Will gets the chance to become partner of his firm. Will's boss Margot wants Will to bring along Vince to a dinner where it is decided if Will will be partner. But Will is kind of embarrassed by Vince, who starts to annoy him. It gets worse when Vince shows up at the dinner and has just got fired from a job by Harry Winston. Margot introduces Grace to Leonard, but he is quite older than Grace expected and surprisingly he is also ...
Will mourns over his break-up with Vince, so Jack decides to take him on a Boy's night out to make him feel better. At first, Will has fun, but after Jack dumps him and leaves him alone at the club Will is mad at him. Scott shows up again to tell Karen that he still wants to ruin her life. After failing the last time, he promises he won't this time. Grace has an important job for a restaurant and as it turns out her client is Scott. Since Grace doesn't know who he is and that he has evil plans, she doesn't realize that Scott wants to talk her into firing Karen.
Scott keeps sending flowers to Karen after falling in lover with her. But Karen got to know someone online and is about to meet him on Valentine's Day. Will and Jack accompany Karen to her blind date with the stranger, because she promised them there would be a lot of gay men. But instead of gay men, the only people there are old and straight in Jack's and Will's opinion. Also, Beverley Leslie and Scott are there. Grace meets Nick when he accidentally comes into her office and they get along very well.
Grace meets Nick again when he picks up his phone which he forgot at her office. After passionately kissing him, Grace is scared she's moving too fast in their relationship, so she convinces Will to go with her on a date with Nick to watch over her and her actions. Karen has a Peeping Tom and she and Jack confront him. It turns out that he wasn't looking at Karen but at birds and that he is a "Hot Gay Nerd". Jack is very interested in this very rare "species" of gay men
As Karen's lawyer, Will warns her that she is spending too much money - it isn't going to last forever. Karen agrees that she could let the pastry chef go. Nick is taking Grace to Union Square Café. When he learns that Jack is working for a TV network, he reveals that he has a script and he would like Grace to read it and then pass on to Jack. Will goes to tell Karen's pastry chef that Karen is letting her go, but he isn't prepared to find out that the pastry chef is fabulous...
It's Grace's father birthday and since her sisters are not able to attend the birthday party, Grace is scared of being alone with her parents. She convinces Karen to accompany her and when they arrive at the parent's house it turns out that Grace's mother is about to leave, too. This means that Karen, Grace and Marty Adler are all alone. After recovering from a first shock, Grace sees this as a chance to improve her relationship with her father. In the meantime, Jack convinces Will to go on a blind date. The date turns out to be blind man, who tells Will that he ...
Jack meets an old student from his acting class, whom tells him about his successor Wendell. When Jack meets Wendell, he realizes that Wendell teaches the "McFarland method" which he stole from Jack. Jack wants to take the class over, but Wendell doesn't let him do so. After having an accident at the Jeans store, Grace is worried about dying one day. Grace decides to make a will and wants to leave some money to Will. When she confronts him about how much money he leaves to her, he doesn't want to tell. So, Grace asks Will's mother Marilyn, who is the only one who ...
After having quit his job, Will thinks is new destination is to become a writer. When he is in park, Will meets Malcolm. Beverley files Karen with a law suit for defamation of character when she publicly said that he is a homosexual. Beverley wants her to apologize for what she said publicly. If she does so, he will draw back the law suit. Jack has to deal with a former child star named Randall, who is supposed to host a show for Out TV. Grace meets her former boyfriend Tom and he introduces her to his wife Viv. It turns out that Tom and Viv bought a hotel and want ...
After his first day, Will becomes suspicious of his new job--especially when he finds himself in an empty office with no coworkers, a German shepherd, and a Russian-speaking thug.
Grace contemplates having an affair with a married man. Elsewhere, Jack begins new career as a host of his new talk show "Jack Talk." Will gets some advice from Malcolm and tries to hide from Karen the fact that Stan is alive. Alec Baldwin and Eric Stoltz guest star, Shelly Morrison also stars.
Karen feels rattled by Stan's return and Will steps in to help her. Meanwhile Grace is labelled homophobic after her comments on Jack's talk show are misconstrued by gay men from all over New York.
Grace goes on a blind date and Jack gives Will swimming lessons.
Karen is forced to come to terms with her feelings for her presumed-dead husband when Jack gives his opinion on her men dilemma. Karen refuses to forgive Stan and wants nothing to do with him--until she learns how willingly Stan gaver her up to Malcolm. Meanwhile, much to Grace's dismay, the new, altruistic Will begins doting on an elderly man whom he invites to their 10th Anniversary Game Night Spectacular.
The day before Will’s charity auction and carnival, Jack meets and begins dating Baby Glenn (guest star Jason Biggs), 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 (guest star Alec Baldwin), 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.
Grace and Will spot her ex-husband, Leo (Harry Connick Jr.), on their plane to London, and Will charms a pair of gay flight attendants into letting Grace into first-class to talk with Leo.
Jack's decision to move makes Will take a close look at their friendship; Karen and Grace are invited to the memorial celebration for Beverly's (Leslie Jordan) deceased wife.
When Grace finds it impossible to please her mother (Debbie Reynolds), Jack offers to help, believing no one knows how to be a good daughter like a gay son.
When the gang spends Christmas at the home of Will's mother, Marilyn Truman (Blythe Danner), Grace gets romantic with Will's brother.
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 accepts a HAPI award for Best Local Cable Gay Talk Show Host. 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.
As Grace prepares for her green-card marriage to James (Taye Diggs), she frets that Karen is going too far by planning an overly lavish spectacle including a performance by the legendary Hall and Oates.
A nervous Grace finally decides that it is time to tell Leo that she is pregnant with his child, but she receives some unexpected news when she works up enough courage to actually go and meet him. Meanwhile, Will is settling in with James and Jack tries to document every second of Grace's pregnancy for his talk show. Karen meanwhile 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. Debra Messing and Megan Mullally also star.
After a large corporation takes over OutTV, Jack's (Sean Hayes) talk show "JackTalk" is completely revamped. An immediate change comes when the new conservative owners hire Amber-Louise (guest star Britney Spears) as "JackTalk's" new co-host. While Jack is deciding whether or not he'll stand up to his new bosses, Karen (Megan Mullally) goes baby shopping. After seeing Grace (Debra Messing) so happy about her pregnancy, Karen decides she wants a baby of her own and offers to pay a make-up lady, Cricket (guest star Wanda Sykes), to carry one for her.
After losing his job as the host of "JackTalk," Jack (Sean Hayes) vows never to return to acting. An unrelenting Karen (Megan Mullally), 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 (Debra Messing) accompanies Will (Eric McCormack) 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 (guest star Bobby Cannavale) 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 (guest star Bobby Cannavale) 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 (guest star Bobby Cannavale) 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 (guest star Bernadette Peters), who was injured as a child during a game of Twister. Jack, on the other hand, is comforted by a man (guest star Josh Lucas) after a devastating discovery when his new show "The Badge" premieres.
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.