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-fiance 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.
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 sportscaster 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 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.
Will returns from vacation to discover that Grace's romantic relationship with neighbor Nathan is humming along. Nathan feels neglected when Will and Grace resume their chummy friendship, complete with their own private language and code. Meanwhile, Jack proudly takes his new-found son Elliot shopping for school at Barney's while Rosario and Karen each cruise the merchandise looking for the perfect "anniversary gift".
The new lawyer in Will's firm is the same lout who bullied him as a child; Nathan's birthday flusters Grace, who's outdone in the gift department by Karen.
Jack is puffed up with paternal pride as he escorts his long-lost teenaged son Elliot to a junior high school dance but not before he coerces Grace into posing as Elliot's date, 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. Grace is so moved to help her worried friend that she moves right into Karen's deluxe apartment-in-the-sky, where she becomes a demanding guest who's soon hooked on servants, bubble baths and an extravagant lifestyle. Meanwhile, as Stan's attorney, Will struggles with stage-fright when he babbles on during a TV news interview, so Jack convinces him to polish his communication skills by attending an acting class ruled by an imperious teacher.
In a sneaky ploy to bum a night off from work at Barney's department store, a conniving Jack plays matchmaker and takes advantage of his geeky female supervisor's interest in Will, while mindful of Will's fantasy of modeling in the store's catalogue. Jack parlays their mutual desires into a "date", even though his unsuspecting friend doesn't have a clue of her intentions. Elsewhere, Grace goes where no woman should when she compares her previous sexual experience with her boyfriend Nathan's.
During an intimate moment, Nathan pops the question of marriage to Grace but she recoils simply because the situation didn't fit her childhood fantasy of a proposal. When she realizes her mistake, she returns the favor, but doesn't get the response she hoped she'd get.
While a baleful Grace wallows in bed as she grieves over losing her boyfriend Nathan, an enterprising Will tries all his old tricks to spring her from her mattress and back into the real world's whirl. But when Jack and Karen arrive, Will fears that their bizarre efforts to help might actually drive Grace futher into her shell, not to mention therapy.
Will and Grace elect to disagree when it comes to choosing sides during a mayoral election; she supports the female Jewish candidate and he's voting for the gay nominee. To settle matters, the roomies host fund-raisers attended simultaneously by both aspirants.
Rather than be apart on Thanksgiving Day, Will and Grace join Jack and Karen for a festive holiday motor tour of their respective dysfunctional families, including Grace's domineering mother as well as Will's willful mom and Jack's stepdad—with unsettling results. Meanwhile, back home, a waiting Rosario bastes and tastes their juicy turkey.
This episode is also known as "Thanksgiving." Will and Grace join Jack and Karen in a motor tour of their respective families. (Double-length Episode)
At the gym, Will spies another guy who looks maddeningly familiar, while Jack gets a workout as he keeps repeating one of his nonsensical catch-phrases 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 for the money—even if she has to resort to drastic measures to get the point across.
Grace is hired as seasonal help to decorate the Christmas display windows of fashionable Barney's; Will meets a ballet dancer but is too embarrassed to introduce his friends.
Will & Grace try to lure Tina, Will's dad's mistress, away from Will's father by setting her up with another man. Unfortunately the only man available is Will's gay friend, Larry. Also, Karen buys a horse for breeding, but the stud is more interested in stallions.
While visiting Karen's incarcerated husband, Grace re-discovers a handsome high school friend who's also doing time in prison, and despite Will's advice, she's soon dressing up and visiting the inmate while dreaming of a life together outside the Big House. Conversely, a sympathetic Rosario chides Karen for not standing by her man—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-fiancée. "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 place—despite the efforts of Sandra Bernhard—but to finance the move, they illegally sub-let their old apartment. Meanwhile, a well-intentioned Jack begins filming a documentary of Karen's colorful life to celebrate her birthday but accidentally stumbles upon her estranged, lowlife mom.
After Will and Grace move into their expansive new dream apartment, they discover the awful pangs of separation anxiety as they pine for their smaller old digs now happily occupied by their friends who sub-let the place. Elsewhere, Jack tries to reconcile Karen with her estranged grifter of a mom, who wants to recruit her daughter for her next caper.
Will presents his newly reconciled parents with a cruise for their anniversary, but their individual secrets ruin his hopes.
In the aftermath of his parents' divorce, Will salvages a beloved garden gnome, 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.
Teaching a design seminar challenges Grace; chaperoning Jack's son occupies Will at the youth's basketball tourney.
Will expects two friends to arrive in New York to plan a wedding, but when the bride-to-be falls ill, he asks a willing Grace to work with the clueless groom to work out the details, 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 means—all leading to mis-conceptions. Meanwhile, Jack considers giving up his show-business aspirations, until he gets some career advice from a “divine” entity: his idol Cher. Likewise, married Karen is sorely tempted by the romantic tickling of a rich and natty gentleman.
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.
Following the 100th episode, the cast looks back at their hit series with clips and bloopers.
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 everyone including Grace's outspoken mom and the subdued Mrs. Marcus 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.
Grace's wedding to Leo leaves Will feeling upset over losing his best friend.
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" 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.
Alternately flirty and shy, and acting “incredibly” like a schoolgirl, Karen falls for a suave and sexy restaurateur. The two of them seemed to hit it off on their first date, but then, he hasn't called her in three days. So buttinsky Grace makes it her mission to confront Prince Charming and find out why. Elsewhere, Will and Jack join a gay men's soccer team, and Will, for one, is hardly having a ball. "They were running and kicking and pushing each other down." he says. "It was supposed to be gay sports. Where were the lingering hugs?"
New relationships discomfit Will and Grace. For starters, Karen fixes up Will with her cousin Barry, who, according to his matchmaker, is "handsome [and] hot." So imagine Will's surpise when he goes on a blind date with Barry and finds he's actually a self-conscious, dreadfully dressed geek who admits at thirtysomething that he's just coming out of the closet. Back in Brooklyn in her new digs, Grace entertains her interesting new neighbor: an extroverted masseuse named Julie, who Grace suspects may be too interested in her.
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 three weeks 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.
Demi Moore plays Sissy Palmer-Ginsburg, Jack's babysitter who now becomes his roomate. On the other hand, Will hates her.Grace faces an identity crisis as a wife.
Will finds a guy that he's interested in.
While Jack and Barry have their first date, Will interrupts to confess that he has feelings for Barry. Then Jack and Will give Barry an ultimatum: he must choose which one he would like to date. The decision is made - Will. At her hotel, Karen mocks Rosario by putting on a maid's apron. She is then mistaken for an actual maid by a very handsome maintenance man who has a disliking for the rich. In order to be near him, she and Rosario switch roles. After a week of perfect dates, Will tells Barry that he wants their relationship to be exclusive. However, Barry claims that he needs to play the field more and see what's out there before he settles down.
Will, Karen and Will's boss Mr. Stein (Gene Wilder) form an anti-romance club thanks to Will and his recent break-up with Barry. The three hold two meetings claiming that "love stinks" until Karen and Mr. Stein form a budding relationship. The two carry on having sex and dating behind Wills back not wanting to hurt him. Will breaks up the club after he finds out claiming that "If you're going to form a club for people who are alone and bitter, you have to at least stay bitter." Meanwhile, Grace decides to make a sexy video for Leo who is away in Africa. Jack wakes up to the sound of her singing and tells her that that's not sexy at all. He invites her to his acting class where the students are supposed to be very open to each other. Grace attends one class, but finds that it isn't helping one bit. Jack films her taking a shower without her knowing it. When she sees the tape, she agrees that it is very sexy only to find out that Jack has been sharing it with his class.
Will attempts to sneak Leo back from Africa to surprise Grace for her birthday. But things don't quite go as planed. All starting with when Grace runs into Leo who arrived a little too soon. But, to spare Will's feelings, they agree to act like they never saw each other. Grace asks Karen and Jack to keep Leo busy until her "birthday surprise." Unfortunately, the duo takes their mission too seriously.
Karen looks for a place to live, and succeeds in finding an apartment with a gal named Liz. Liz turns to be just as self-important and skanky as Karen, so it's a perfect match. Meanwhile, Grace and Jack are concerned about Will when he gets injured and relies heavily on painkillers.
The divorce proceedings begin, and Karen is shocked to learn that Will is Stan's lawyer, not hers. On a whim, she hires Soupie, a wet-behind-the-ears lawyer with a child's mentality. Meanwhile, Grace is caught in a social faux pas when her biggest client ever has an on-again, off-again relationship with Jack.
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.
Karen, Will, Jack, and Grace go on a trip in Karen's yacht to sprinkle Stan's ashes into the Caribbean while Leo is flying to Guatamala with an atractive co-worker. While Karen sprinkles Stan's ashes she finds Lorraine has been stowing on board. While Karen and Loraiinne fight, Will and Jack get drunk. Lorainne pushes Karen off the board and Rosairo jumps off after her. The next morning Grace finds Leo's bag with a letter from his co-worker Danni saying that she wants Leo. Will wakes up in bed naked with a hangover and a naked Jack in the bed with him. Meanwhile Karen and Rosairo are stuck on a cargo boat.
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 and 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 dog 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 Peninsula hotel only to discover occupant to be her father Lester.
Will learns that Karen missed her physical, so he takes her to one of the finest doctors in the city. It is not until after the doctor does a demonstration on Will that Karen obliges. While at the office, Jack flirts with a male nurse, and he later announces that he's going to be a nurse himself. The problem is, training costs $2,700, and Will and Karen are reluctant to give him the money. Once they pay the fees, Jack, fickle as ever, announces that he's taken up surfing, and that he needs $1,600 for lessons. Will and Karen are about to let the nursing school know of his decision to drop out until Jack comes up with an inventive way to feed Karen her calcium pills.
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.
Hoping to cheer up Grace, a well-dressed Will takes his best friend with him on a dinner date. When the date stands him up, Will catches the eye of a female patron while Grace bumps into a guy with whom she once shared an ordinary, forgettable romantic encounter. Meanwhile, Karen takes student nurse Jack out to celebrate his school "success" but the evening turns sour when Karen runs into her ultimate nemesis, Candice Bergen. The meeting sparks yet another round in the Bergen/Walker Prank War of 2003.
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. And Karen is embraced by the inspiring music of Manilow waiting in line with a Fanilow named Cheryl.
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 of marriage, 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 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 but when Jack decides to include his new boyfriend, the gourmet attorney finds himself a 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.
Will and Grace ride the success of their recent real-estate venture to expand to the East Side but clash with the reigning champs of "apartment flippers" lesbians Deirdre and Monet. Fighting against their new competition's intimidation tactics, the enterprising duo must rely on Will's masculine sex appeal in the hopes of dividing the same-sex real-estate moguls. Meanwhile, Karen seeks the spiritual guidance of John Edward in order to comfort her guilt over her recent engagement.
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 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 show will be going off the air forcing them to say goodbye to their six favorite Friends and a psychiatrist named Frasier Crane.
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 forgo a picturesque fall wedding to elope in Las Vegas, Karen hops a plane to "Sin City" with fiance Lyle and faithful friends Will and Jack but when she bumps into vacationing superstar Jennifer Lopez, she asks J-Lo to sing at the ceremony. Meanwhile, Leo returns from Cambodia to meet up with Grace at the wedding, but their reunion is delayed by a freak design accident.
Opting to forego a picturesque fall wedding and elope in Las Vegas, Karen hops a plane to "Sin City" with fiance Lyle and faithful friends Will and Jack. After arriving, they bump into superstar Jennifer Lopez who is vacationing and agrees on behalf of Rosario to sing at the ceremony. Meanwhile, Leo returns from Cambodia to meet up with Grace at the wedding, but their reunion is delayed by a freak design accident.
Jack and Jennifer Lopez return from her summer tour to relax, but a pushy Karen recruits Jack to help her get Lopez'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 and Vince.
Free food lures Grace to an AA meeting, where she runs into Val. Meanwhile, Jack starts work as a TV executive at a gay network, something which Will is not aware of when he comes to the network for an appointment so he can give suggestions.
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 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.
A birthday party for Will (who's 40 going on 37) is an uneasy celebration, thanks to a symbolic gift from his new lover that betokens commitment. The strangest present: a nude portrait of Will that's lacking in certain details.
Grace and Karen are hired to decorate an apartment of a newlywed couple and they want their place to be all about love. Will Grace and Karen, two newly divorced women, be able to do the task? Meanwhile, a doomed bookstore gets help from Will... sort of.
When Will and Grace invite Vince and 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 decides to leave the interior design 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. 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.
The group 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 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 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. Meanwhile, 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. While lunching at the mall they start making fun of people, but Karen's remarks are especially mean and Olivia and her friends take offense.
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 shows a presentation that wows the board, he takes 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 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 Haley Joel 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 Woolley. Grace and Karen decide to trap him in his lie. Meanwhile, Jack takes Will out for a boys' night to get his mind off of Vince, but ends up abandoning Will at the club. In an effort to make it up to Will, Jack takes him out to lunch and tries to ignore everyone around him except, Will. The task becomes incredibly difficult once Jack realizes Patti Lupone has entered the restaurant.
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 Wooley 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 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. Meanwhile, Ellen asks Grace to babysit her kids for a day, but when Karen wants to get involved, Grace epresses her doubts about Karen's ability to take care of children.
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 and she becomes overly critical of Jack.
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. Meanwhile, 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." Realizing he needs new material to get back into teaching, Jack changes his method to win back his students.
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 OutTV, but spoiled child star Randall fails to embody Jack's vision. Under threat of a lawsuit, Karen is forced to publicly apologize to Beverly 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.
This Behind-the-scenes exclusive on the famed TV show, Will & Grace, tells about each character individual, and together. This aired on Lifetime in September of 2005, because Will and Grace started syndication on the Network.
LIVE SEASON PREMIERE - 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 labeled 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 gives 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.
While flying to London, Will and Grace notice that Grace's ex-husband Leo is on their flight.
Will is thrilled to help Jack look for another apartment when he decides on a whim to move, but after getting involved in an effort to help two gay penguins from being separated at the zoo, he begins having second thoughts about the idea of Jack moving. While attending Beverley's wife's memorial "celebration, " Karen and Grace experience a wardrobe malfunction, which they must try to conceal.
Grace asks Jack for help on how to deal with her domineering mother, and on his first day Will pursues a slumlord.
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. 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.
Karen celebrates her birthday with some of New York's crème de la crème, but the festivities turn sour when she ends up crammed in the bathroom with Grace, Will and Jack, who have all embarrassed themselves at the party.
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 are dreading a would-be dull dinner date with married friends Rob and Ellen, but the couple spices things up by making an important announcement. Their focus changes however when their server ends up being none other than Will's ex-boyfriend, Vince (guest star Bobby Cannavale). Elsewhere, after Jack decides he needs to spice up "JackTalk" by pulling an Oprah and helping a fan come out of the closet, he and Karen setup a bowling alley meeting with his fan when Karen is recruited to join a woman's league game as an emergency fill-in.
The gang travels to Los Angeles to accompany Elliot while he visits UCLA. Coincidently, Will runs into James who's in jeopardy of being deported. After spending a perfect weekend together, Grace makes a proposal to keep Will and James from having to say 'good-bye' to each other... ever again...
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.
While Jack talks Will into going to a cowboy-themed gay bar to meet his new boyfriend, Grace's 'liberal guilt' leads her to hiring a minority as a second assistant, against Karens wishes.
A big corporation takes over OutTV and completely revamping Jack's talk-show and gives him a conservative co-host. Meanwhile, Karen decides she wants a baby of her own and offers to pay a make-up lady to carry one for her.
After losing his hosting job, Jack vows never to return to show business. Despite this, Karen decides to do whatever it takes to get Jack to audition for another job. Meanwhile, Grace goes with Will to a dinner at his parents' home, where Will's father gives Will's cherished baby blanket as a gift to Grace's unborn child.
Will grapples with the untimely death of his father after their last encounter; Grace begins to doubt her potential to be a good mother.
Will and Grace begin attending lamaze classes together, Grace starts to doubt whether Will is up for raising a child with her when and Vince take another chance at having a relationship. Meanwhile, Karen looks to Jack for comfort while her marriage is on the rocks, but finds that Jack is a little preoccupied with his new television show.
Vince's plans to move into a brownstone with Will do not include Grace; Meanwhile, Karen shocks everyone when she announces that she has a sister, Gin, who was injured as a child during a game of Twister and Jack's new show debuts.
An hour-long series retrospective spanning the popular show's 8-year run. Includes interviews with the cast, crew, and guest stars.
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.
An hour-long series retrospective spanning the popular show's 8-year run. Includes interviews with the cast, crew, and guest stars.
The cast and creators present a star-studded tribute celebrating Will & Grace's return!
Will and Grace both falter when their political beliefs are put to the test; and Jack and Karen help them hide their secret shame from each other, but the truth finally comes out.
Will and Jack try to date younger guys but find it challenging. Grace and Karen experience a crisis that reveals Grace's true feelings about Karen.
Grace is shocked to find that the emergency contact called by her doctor's office is ex-husband Leo, not Will. Jack takes on a new job he never expected to love. Karen befriends a 12-year-old girl in the Bronx, despite her best efforts.
Jack is stunned to learn that his estranged son, Elliot has a son of his own, Skip. Moreover, Skip needs the kind of help only Will and Jack can provide. Grace and Karen behave badly with the hot new guy at work.
Grace tries for her biggest job yet: decorating a string of boutique hotels for an obnoxious mogul. Meanwhile, Will is surprised at his reaction to making Senior Partner; Beverley Leslie discloses his secret to Karen; and Jack owns half of a winning lottery ticket.
When Karen has trouble dealing with a personal tragedy, Will, Grace, and Jack try to intervene. Will and Grace's new business relationship begins to show signs of stress.
Will, Grace, Karen, and Jack wish they could have experienced Christmas in old New York City, but realize the past was not quite as romantic -- or open to diversity -- as they pictured it.
Will and Grace try to convince themselves they are okay with dating the same man; Jack and Karen get an annoying commercial jingle stuck in their heads and must seek medical attention.
Will and Grace's old friend Larry decides he's in love with Will. On Jack's first day as a Lyft driver, he hits his wacky neighbor Val. Karen steps in to bail out Jack, but then needs Jack to bail her out.
Will, Grace, Jack and Karen attend the wedding of Will's ex-boyfriend, Vince. While Grace tries to keep Will from making a scene, Jack learns that his wedding hookup has many strings attached.
Jack's intimacy issues are challenged by a closeted boyfriend; Will and Grace sell their new line of bedding on live television.
Grace is horrified to realize that she's dated three men from the same family; Will and Karen get on each other's nerves at the office until they bond over watching -- and producing -- their own little telenovela.
A baby shower makes Grace and Will question their life choices; Karen and Jack find a way to combine child labor with musical theater.
Against Jack's advice, Will rekindles a relationship with his first love; Grace reluctantly fights for Karen's civil rights when a bakery refuses to make a cake she wants.
Grace brings Will for support when she goes home to celebrate her deceased mother's birthday; Jack's faith in love is crushed after a breakup; a secret in Karen's marriage is uncovered.
Grace's father and Will's mother end up making a surprising and upsetting connection; Jack rebounds from his breakup with a new love; Karen must decide between her husband and her lover.
Grace’s accidental run-in with Noah, a curmudgeonly man she follows on Twitter, hints at a possible new love interest. Jack wants to look younger before meeting Estefan’s family on Skype but makes a terrible first impression after overdoing the numbing cream before his facial procedure. Meanwhile, Will helps Karen protect the intellectual property rights of her most prized possession.
Will, Grace, and Jack are upset when they discover they’ve been too preoccupied with the changes in their own lives: Will teaching law at Columbia, Grace running for president of the New York Interior Designers Society and Jack’s new relationship with Estefan to even notice Karen has not been seen in days – ever since her husband found out about her affair with Malcolm.
Will and Jack visit Jack’s grandson, Skip, in Texas to watch him perform at his church’s talent show. But when Jack learns Skip plans on singing “Diamonds Are a Girl’s Best Friend,” he becomes afraid for his grandson’s safety. Karen tags along to check out the portion of the border wall she sponsored, only to discover that Beverley Leslie has claimed it as his own. Grace and Noah try to figure out if something is wrong in their relationship because their attempts to have sex have failed.
Will and Grace discover old letters written to each other from their college days, and decide to read them together. But reminiscing about the past turns ugly when a major bombshell is revealed in one of the letters. Meanwhile, when Karen announces she’ll never fall in love again, Jack channels Rosario – or does he? – to convince her it’s never too late to find love
Grace joins her father on a road trip, and a secret from her past is finally revealed, causing father and daughter to address something that will change their relationship forever. Meanwhile, Will, Karen, and Jack celebrate Jack’s engagement at a gay bar run by legendary drag queen Miss Coco Peru. When it’s revealed that Jack has chosen both of them to be his best man, Will and Karen have a lip-sync monologue throwdown to determine who truly deserves the coveted title.
Will discovers that Noah has a child he hasn’t told Grace about, but is now sworn to secrecy. Karen and Jack’s relationship is tested when she fires him from the play she’s producing and replaces him with Jon Cryer.
Grace unintentionally meets Noah’s daughter Katie; Will’s mom Marilyn visits after the death of her beloved dog, but doesn’t get the emotional support she expects; Jack argues with his rec center boss, Theo.
In order to land a handsome TV news anchor with a penchant for dim, silly men, Will seeks advice from Jack on how not to be himself; Karen enlists Grace to help get photos of her ex Stan’s affair with Lorraine Finster.
Will, Karen and Jack unknowingly take a hallucinogenic drug, which causes Will and Jack to wonder if they’re each other’s soul mate and has Karen giving her last “performance” as Mrs. Stanley Walker. Meanwhile, Grace is shocked when her high-powered client takes up with her sister Janet.
Will and Grace’s plan to win over Will’s new Columbia department head goes awry when he drops dead in their apartment – and they use his phone to text his full recommendation of Will. Karen and Estefan’s dislike for each other puts Jack in full damage control mode when he must keep them separate at his birthday dinner.
When Will discovers Karen’s estranged stepdaughter Olivia is a student in his law class, he attempts to solve their issues with a mock trial. Grace and Jack go on a diet together, but giving up their eating habits proves harder than anticipated.
Malcolm enlists Grace to help him win back Karen’s affections. Will’s flirtation at work lands him in an ethical dilemma. Jack’s passion for performing is reignited by a chance encounter with Zusanna, the sister of his former acting teacher.
Will gives local newscaster McCoy Whitman a second chance and, with the help of Jack, finally gets to know the man behind the newsman. Grace’s campaign for Design Guild President hits a snag when the deciding vote comes down to her old nemesis, Val. Karen acts as Grace’s campaign manager, and attempts to secure Val’s vote by any means necessary.
Jack’s insistence that Will be nicer to Estefan backfires; Grace unknowingly knocks over a prominent figure. When Karen discovers Noah plans to kill off the main character of her favorite romance novel, she forces him to rewrite the story.
After her dad, Martin, is rushed to the hospital, Grace is shocked when he refuses a transfusion of Will’s blood. Will’s mom, Marilyn, uncharacteristically takes Martin to task. Karen’s demands cause Jack to uninvite her to his wedding.
When both of their boyfriends ask to move in, Will and Grace use each other as an excuse to get out of it. A snowstorm traps Karen at the office and Jack in an elevator, where he reunites with old flame Drew and tests his commitment to monogamy.
Jack realizes he lost 13 gold coins he’s supposed to give Estefan at their wedding to avoid a curse. Will is concerned that Grace is the only one compromising in her relationship with Noah. Karen shows up at a dinner party with her new date, Nikki.
Jack and Estefan’s romantic wedding in Spain takes a detour when their flight is cancelled, forcing them to get married at the airport by their friend Miss Coco. McCoy’s big job offer in London has Will worried about engaging in a long-distance relationship. While dealing with doubts about her current relationship, Grace meets a charming guy at the airport who inspires her to make an impulsive decision. And advice from Smitty makes Karen reconsider her commitment to Nikki and her own sexual orientation.
Grace returns from her European travels a new woman, but her elation is short-lived when she receives life-changing news. Karen teaches Will how to be better at phone sex. Jack has a yard sale to discreetly get rid of Estefan’s annoying cuckoo clock.
When Grace admits she’s not sure who’s the father of her baby, Karen orchestrates a “Mamma Mia” situation with the potential baby daddies. Will worries what will happen if he has a straight son and enlists Jack to help him prepare.
Will discovers a way to finally get back at Jack for years of mocking his hairline. Grace is determined to prove to Mrs. Timmer she’s strong enough to handle being a single mother. Karen squares off against Stan’s brother in a poker game.
Will and Grace get competitive over whose process of having a baby is more difficult. Jack helps Karen prove that she’ll be a competent owner of her new baseball team, but Karen realizes that an old acquaintance may be the help she really needs.
In the aftermath of Will and McCoy breaking up, Grace and Jack hire the Grief Panda to help Will process his pain. With Karen completely occupied with her new baseball team, Grace believes that she has to fire Karen in order to set her free.
Committed to becoming a father on his own, Will meets a potential surrogate with stellar reviews, but her lifestyle choices give him doubts. in order to gain entry to AnnieCon, Grace pretends to be a formerly famous Annie.
Grace and her neighbor give their romance another shot. However, an embarrassing incident puts Grace's relationship, and her dignity, in jeopardy. Will decides it's time for Jack to grow up and cuts him off financially.
When Larry warns Will and Grace about the difficult entry process into the elite school they both want their kids to go to, they set out to prove that their child would be the better candidate. While helping Jenny with her ASMR livestream, Jack unwittingly creates problems between Karen and her "booty buddy," Luke.
Will and Grace decide to intervene when they discover Grace's niece is dating a bisexual man. Jack gets permission from his husband to sleep with his celebrity hall pass. Karen struggles to adapt when her assistant books them on an economy flight.
Marilyn goes behind Grace's back to fix her up with a beagle-breeding couple interested in adopting Grace's baby. Will helps Karen deal with a PR nightmare. Jack and Estefan go to extreme lengths to get rid of a mouse.
Grace and her neighbor, James, give their relationship one more shot, but when James invites Grace to his job at the aquarium, she endangers his job and a species. Jack takes Will to an unexpected place to blow off steam -- church.
Karen introduces Will and Grace to the new love of her life, Phil, but Will and Grace become suspicious that he has sinister intentions. When Miss Coco Peru tells Jack that he's closing down his bar, Estefan encourages Jack to become its new owner.
Will and Grace race to save Karen when they think she is in danger after her new boyfriend takes her to a cabin in the woods. Jack makes up a story to a snobby reporter in order to keep his new bar relevant after its previous owner steps down.
Jack helps Karen sneak into the manse to retrieve her ring, but they're shocked to find it on the hand of Stan's new girlfriend. While hosting Will's surrogate for the weekend, Will and Grace become the old folks they swore they'd never become.
Will ropes Dr. DiLorenzo into going on a fake date so he can spy on his surrogate. Grace struggles with popping her gender reveal balloon Karen is torn between celebrating her team's championship and helping Jack with his Broadway audition.
Will claims living with Grace is like Ricky living with Lucy. When Karen and Jack hear this, they each claim that they are the Lucy of the group. Grace, Karen and Jack each imagine themselves as Lucy, with Will as the Ricky to all of them.
Karen celebrates her baseball team's championship. Will and Grace go to an open house, which leads to a conversation about their future living arrangement. Jack has to decide if he wants to stay in the city to pursue his dreams.
Will is determined to not reminisce about his life in the city or his ex; Grace has false alarms of going into labor; Karen attempts to get closure with her ex-husband. Jack's dream of taking a bow on a Broadway stage becomes a very real possibility.
Hosted by Eric McCormack, this special retrospective will show clips of past and present episodes that highlight the series' most iconic and memorable moments. The look back will also feature emotionally-charged reactions from "Will & Grace" superfans and celebrities who will share stories about what the show has meant to them. Elton John and Norman Lear will also make special appearances.
NBC remembers some of the past guest stars and their quirky bloopers from its Emmy Award winning comedy "Will & Grace." Hosted by series star Eric McCormack, the special includes such past guest stars as Matt Damon, Glenn Close, Michael Douglas, Cher, Kevin Bacon, Demi Moore and Madonna.
UK documentary on the success and legacy of the show Will & Grace.
Extended interview with series creators, David Kohan & Max Mutchnick.
Debra Messing (Grace) and Eric McCormack (Will) share their experiences working on the hit tv series.
Ten years after the finale of "Will & Grace", the cast reunites for the first time ever to take on the 2016 Presidential Election in their own inimitable way.
