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.

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.

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.

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.

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.

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.

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.

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.

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.

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

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

When 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.

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.

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.

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.

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.

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.

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.

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.

Just as Will and Grace are settling into the idea of raising the baby together, Will's boyfriend Vince surprises him with an announcement that will ultimately lead Will to choose between his commitment to Grace and his relationship with Vince.