Will & Grace

Jack's insistence that Will be nicer to his fiancé, Estefan, backfires when Estefan thinks Will is in love with him. In a hurry to buy her boyfriend Noah a Valentine's Day gift, Grace unknowingly knocks over a prominent figure while going after a taxi. And when Karen discovers that Noah not only writes her favorite romance novels but also plans to kill off the main character, she forces him to rewrite the story.

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.

Grace is enlisted by Malcolm to help him win back Karen's affections. Will's flirtation with his co-worker, Paul, takes a turn when details about Paul's home life put Will in an ethical dilemma. And Jack's run-in with Zusanna, the sister of his former acting teacher, reignites Jack's passion for performing.

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.

Will and Grace's plan to win over Will's new boss goes awry when he drops dead in their apartment; Estefan and Karen's mutual dislike puts Jack in full damage control mode at his birthday dinner.

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.

In order to land a handsome, gay TV news anchor (guest star Matt Bomer) with a pension for dim, frothy men, Jack convinces Will to not be himself and to act like someone silly and stupid—does he know anyone like that? Karen learns that her alimony will be severely limited unless she can get photos of her ex-husband's affair with Lorraine Finster, so she enlists Grace to go with her to the strip club where Lorraine works.

Will convinces Grace that her boyfriend, Noah, isn't in the wrong by refusing to let her meet his daughter, Katie. When Grace goes to apologize to Noah, she unintentionally meets Katie. Meanwhile, Will's mom, Marilyn, visits after the death of her beloved dog, and becomes upset when she doesn't get the emotional support she expects from her son. And Jack gets into an argument with his rec center boss, Theo.

When Will discovers Noah has a child, he promises to keep the secret from Grace; Karen and Jack's relationship is tested when she fires him from the play she's producing and replaces him with Jon Cryer.

While on a road trip with her father, Grace reveals a past secret, changing their relationship forever; legendary drag queen Miss Coco Peru emcees a lip-sync monologue throwdown to determine who will be Jack's best man, Will or Karen.

Now a certified psychic, Jack channels Rosario to help Karen open her heart to love again; Grace learns love means having to say you're sorry... to Will.

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. Back home, Grace and Noah try to figure out if something is wrong in their relationship because their numerous attempts to have sex have failed.

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.

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.

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.

Jack's intimacy issues are challenged by a closeted boyfriend. Will and Grace sell their new line of bedding on TV.

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 hook-up has many strings attached.

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 and Grace try to convince themselves they are okay with dating the same man, the charismatic "Bad Boy of Bread". Jack and Karen get an annoying commercial jingle stuck in their heads and must seek medical attention.

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.

When Karen's has trouble dealing with a personal tragedy, Will, Grace, and Jack's try to intervene. Will and Grace's new business relationship begins to show signs of stress.

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; Beverly Leslie discloses his secret to Karen; and Jack owns half of a winning lottery ticket.

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 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.

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.

We pick up with Will, Grace, Jack, and Karen 11 years since we last saw them. Will and Grace both falter when their political beliefs are put to the test. Jack and Karen help Will and Grace hide their secret shame from each other, but the truth finally comes out.

Friends and family gather for the funeral of Will's father. At the reception everyone shares with Will fond last memories of his father, while Will's last memory of his father is not as pleasant. Marilyn helps him realize the changes needed in his life.

After losing his job as the host of "JackTalk," Jack vows never to return to acting. An unrelenting Karen, however, will not let Jack give up on his passion and decides to do whatever it takes to get Jack to an audition.

After a large corporation takes over OutTV, Jack's talk show "JackTalk" is completely revamped. An immediate change comes when the new conservative owners hire Amber-Louise as "JackTalk's" new co-host.

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 bar fight.

A nervous but optimistic Grace decides it's finally time to tell Leo she is pregnant with his child, but when she finally works up enough courage to actually meet her ex-husband she receives some unexpected news.

The big day has finally arrived - Grace and James are getting ready for their green card wedding. To Grace's dismay, Karen takes it upon herself to ignore her wish for a low-key wedding ceremony and decides to arrange including hiring Hall & Oates.

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.

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.

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.

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.

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.

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.

Grace finds it impossible to put up with her mother Bobbi's constant nitpicking, so Jack takes it upon himself to help her because, according to him, no one knows how to be a good daughter better than a gay son.

When Jack decides on a whim to move, Will is excited at the thought of helping him look for a place. While attending Beverley's wife's memorial "celebration," Karen and Grace experience a wardrobe malfunction, which they must try to conceal.

While en route to London, Will and Grace spot Grace's ex-husband Leo on their flight. Will charms a pair of gay flight attendants, who also happen to be dating, so he can smuggle Grace into first class to talk to Leo.

The day before Will's charity auction and carnival, Jack meets and begins dating Baby Glenn, who is still riding his fifteen minutes of fame from when he got trapped in a hole for three days in the eighties.

Karen is finally forced to come to terms with her feelings for her presumed-dead husband when Jack surprisingly tells her he thinks she belongs with Stanley, not Malcolm.

When Jack learns that Will never learned how to swim, Jack insists that he teach Will how. Meanwhile, Karen sets Grace up on a blind date with one of Malcolm's friends.

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 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.

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.

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.

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.

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.

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.

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.

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, 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.

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.

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.

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.

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

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.

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 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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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 â€" and uncover a secret pile of cash in the master bed.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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 finds a guy that he's interested in.

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.

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.

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.

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.

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?"

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.

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.

Grace's wedding to Leo leaves Will feeling upset over losing his best friend.

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.

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.

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.

A bicycling adventure tests Will and Grace up in the Catskills with Leo and his pal in a quest for Halloween pumpkins.

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.

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.

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.

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 his laptop computer is stolen, Will meets a sociable police detective who takes a special interest in his case as they go undercover â€" but Will doesn't know that the gumshoe is secretly participating in Jack's therapy group for gays. Elsewhere, Grace is again hassled by her psycho neighbor Val who ""opens"" a rival design business and prospers by stealing Grace's ideas.

Will expects two friends to arrive in New York to plan a wedding, but when the bride-to-be falls ill, he asks a willing Grace to work with the clueless groom to work out the details â€" but she gets a little too involved in the dreamy details and fancies herself a bride instead. Meanwhile, Will and Karen get chummy over a steamy potboiler book that they're both reading which leaves a jealous Jack fuming as the odd man out in the book-of-the-month club.

Teaching a design seminar challenges Grace; chaperoning Jack's son occupies Will at the youth's basketball tourney.

In the aftermath of his parents' divorce, Will salvages a beloved garden gnome â€" nicknamed ""Squatsie"" â€" and proudly plants the childhood relic in his apartment's community area until Grace accidentally delivers a coup de grace on the gnome's dome with a shovel. Elsewhere, Jack consults his acting coach when he fears that his heterosexual role in a mattress commercial produced by Karen will stereotype him for more meaningful gay acting gigs in the future.

Will presents his newly reconciled parents with a cruise for their anniversary, but their individual secrets ruin his hopes.

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 and Grace feel they need more elbow room, so they search for larger digs and find an exquisite placeâ€"despite the efforts of Sandra Bernhardâ€"but to finance the move, they illegally sub-let their old apartment. Meanwhile, a well-intentioned Jack begins filming a documentary of Karen's colorful life to celebrate her birthday but accidentally stumbles upon her estranged, lowlife mom.

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

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.""

While visiting Karen's incarcerated husband, Grace re-discovers a handsome high school friend who's also doing time in prison, and despite Will's advice, she's soon dressing up and visiting the inmate while dreaming of a life together outside the Big House. Conversely, a sympathetic Rosario chides Karen for not standing by her man â€" and bets her boozy boss that she and pal Jack cannot stay penned-up together in the same room for three days without harming each other.

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.

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.

At the gym, Will spies another guy who looks maddeningly familiar, while Jack gets a workout as he keeps repeating one of his nonsensical catchphrases in hopes of seeing it become popular among the sweat set. Meanwhile, Grace gets some bad advice from Karen when she seeks a loan to expand her company so she stoops to asking her wealthy employee herself for the moneyâ€"even if she has to resort to drastic measures to get the point across.

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)

Rather than be apart on Thanksgiving Day, Will and Grace join Jack and Karen for a festive holiday motor tour of their respective dysfunctional families, including Grace's domineering mother as well as Will's willful mom and Jack's stepdad -- with unsettling results. Meanwhile, back home, a waiting Rosario bastes and tastes their juicy turkey.

Will 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.

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.

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.

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.

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.

Jack is puffed up with paternal pride as he escorts his long-lost teenaged son Elliot to a junior high school dance but not before he coerces Grace into posing as Elliot's date â€" which only revives her own tortured memories of rejection from school dances many years before. Elsewhere, Karen has great fun at her lawyer Will's expense when she continues to capriciously summon him for bogus ""emergencies"" â€" that is, until she really needs him.

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.

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".

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 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 â€" 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'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.

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.

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 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.

When Will's surrogate, Jenny, tells Will their relationship needs boundaries, Will ropes newly-out Dr. DiLorenzo into going on a fake date so he can spy on Jenny. Unsure if having a boy or girl is more difficult, Grace struggles with popping her gender reveal balloon. During her baseball team's championship game, Karen is torn between celebrating with Friday, and helping Jack build his confidence for a Broadway audition.

Jack helps Karen sneak into the manse to retrieve her coveted ring, but they're shocked to find it on the hand of Stan's new girlfriend, Val. While hosting Will's surrogate, Jenny, for the weekend, Will and Grace become the old folks they swore they'd never become.

Will and Grace become convinced Karen is in danger when her new boyfriend, Phil, takes her to a cabin in the woods. With the help of Karen's assistant, Friday, Will and Grace race to save her. Jack makes up a story to a snobby reporter in order to keep his new bar relevant after its previous owner, Miss Coco Peru, steps down.

Karen introduces Will and Grace to the new love of her life, Phil. But Will and Grace become increasingly suspicious that Phil has sinister intentions for their friend. When Miss Coco Peru tells Jack that he's closing down his bar for good, Estefan encourages Jack to become its new owner.

Despite her history of transgressions, Grace and her neighbor, James, decide to give their relationship one more shot. But when James invites Grace to his job at the aquarium, she endangers his job and a species. In order to help Will deal with his anxiety about becoming a father, Jack takes him to an unexpected place to blow off steam – church. Karen finds herself in a confessional booth, and a visit from Smitty makes her reconsider their entire relationship.

Worried about Grace being a single mother, Marilyn goes behind Grace’s back to fix her up with a beagle-breeding couple interested in adopting Grace’s baby. Will gets enlisted by Karen to deal with a P.R. nightmare created by a homophobic player on her baseball team. Jack and his husband, Estefan, go to extreme lengths to get rid of a mouse.

Will and Grace decide to intervene when they discover Grace's niece is dating a bisexual man. Jack gets permission from his husband, Estefan, to sleep with his celebrity hall pass, Ryan Phillippe. Karen struggles to adapt when her assistant, Friday, books them on an economy flight.

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.

Grace and her neighbor, James give their romance another shot – even after she slept with his son and his father. But 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. But unlikely wisdom from Jack’s husband, Estefan, makes Will reconsider.

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.

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.

Will and Grace get competitive over whose process of having a baby is more difficult. Jack helps Karen prove to Danley Walker that she'll be a competent owner of her new baseball team. But Karen realizes that an old acquaintance, Amy, may be the help she really needs.

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.

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.

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.

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.

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.

Jack and Estefan's wedding takes a detour when they're forced to get married at the airport by their friend Miss Coco. Will's worried his relationship may turn long-distance. Grace meets a charming guy. Karen reconsiders her commitment to Nikki.

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.

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.

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.

Jack's insistence that Will be nicer to his fiancé, Estefan, backfires when Estefan thinks Will is in love with him. In a hurry to buy her boyfriend Noah a Valentine's Day gift, Grace unknowingly knocks over a prominent figure while going after a taxi. And when Karen discovers that Noah not only writes her favorite romance novels but also plans to kill off the main character, she forces him to rewrite the story.

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.

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.

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.

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.

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.

In order to land a handsome, gay TV news anchor with a pension for dim, frothy men, Jack convinces Will to not be himself and to act like someone silly and stupid. Karen learns that her alimony will be severely limited unless she can get photos of her ex-husband's affair with Lorraine Finster, so she enlists Grace to go with her to the strip club where Lorraine works. Olympian Adam Rippon has a cameo as a barista with an attitude.

Will convinces Grace that her boyfriend, Noah, isn't in the wrong by refusing to let her meet his daughter, Katie. When Grace goes to apologize to Noah, she unintentionally meets Katie. Meanwhile, Will's mom, Marilyn, visits after the death of her beloved dog, and becomes upset when she doesn't get the emotional support she expects from her son. And Jack gets into an argument with his rec center boss, Theo.

When Will discovers Noah has a child, he promises to keep the secret from Grace; Karen and Jack's relationship is tested when she fires him from the play she's producing and replaces him with Jon Cryer.

Grace reveals a secret from her past to her father, changing their relationship forever; legendary drag queen Miss Coco Peru emcees a lip-sync monologue throwdown to determine who will be Jack's best man, Will or Karen.

Now a certified psychic, Jack channels Rosario to help Karen open her heart to love again; Grace learns love means having to say you're sorry... to Will.

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, 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.

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 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.

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.

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 brings Will for support when she goes home to celebrate her deceased mother's birthday. Jack's faith in love is crushed after breaking up with Drew and uncovering a secret in Karen's marriage.

Will rekindles a relationship with his first love against Jack's advice. Grace reluctantly fights for Karen's civil rights when a bakery refuses to make a cake she wants.

A baby shower makes Grace and Will question their life choices. Karen and Jack find a way to combine child labor with musical theater. Jennifer Lopez will pull double duty guest-starring as both herself and her "Shades of Blue" character, Det. Harlee Santos.

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.

Jack's intimacy issues are challenged by a closeted boyfriend. Will and Grace sell their new line of bedding on TV.

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 first day as a Lyft driver goes south when he rear-ends a wacky neighbor. An old friend decides he's in love with Will. Tim Bagley and Molly Shannon guest star.

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, 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.