Will returns from the island to find that Grace and Jack have bonded, leaving Will feeling left out. Meanwhile, Karen feels guilty when her actions lead to Rosario being arrested for smuggling.

Will and Jack's apartment becomes a haven for Grace after a break-in attempt at her place; Meanwhile, Jack and Karen still aren't speaking over the divorce debacle.

Will and Jack can't wait to arrive at the house of two old friends who are known for their wild parties but they discover that the former party animals are now sedately raising an adopted baby girl - and Will shocks Jack when he volunteers to test his shaky parenting skills by babysitting her for them. Elsewhere at a snooty yacht club, Grace believes that Karen is jealous of her romantic relationship with Ben but then later regrets taunting her.

Grace is appalled when an impressionable new intern suddenly emulates Karen and takes on her brass persona, causing the office to go haywire. Meanwhile, Will and Jack muck up a gay-sensitivity seminar for local cops, but the two stray from the peaceful message and get into a fight with two lesbian volunteers when the women accuse them of using sexist language.

Grace finds it hard to call it quits with Ben, whose charm makes her reconsider. Meanwhile, to save his failing cabaret act, Jack unsheathes his claws and writes nasty new material based on Will's private life.

A 'Cyrano de Bergerac'-style plot has Jack borrowing Will's words to impress a crush, while an ex asks an amazed Grace to join him in a threesome with his new lover.

Will reluctantly decides to use a birthday gift certificate from Grace to consult a psychic about his future and encounters Sue, an absent-minded psychic who operates out of her messy living room and whose predictions leave him reeling. Meanwhile, pop icon Cher encounters her biggest fan: Jack; and Karen frowns on Grace's new employee at the design firm.

A crucial confession highlights Thanksgiving 1985, when college student Grace takes boyfriend Will home to meet her family, who then comes out of the closet. Also, we learn how Will and Jack became pals and how Karen ended up with hubby Stan and Rosario.

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.

Will and Jack threaten to destroy their friendship when they both go after the same guy. Meanwhile, Grace meets a great new guy, but she is worried that an ugly sore on her lip will scare him away. But she is the one who winds up being scared away when she learns that the guy has six toes on one of his feet.

When they are asked to read at Joe and Larry's civil union, Will and Grace verbally spar over her self-serving, get-and-take attitude where Will is responsible for everything -- but what's really bugging him is the overwhelming feeling that Grace is behaving more like a wife than an old friend. Meanwhile, Karen tries to help a caffeine-addicted Jack get over a failed crush but he's so jacked-up on java that only a tough-love approach will work.

Will and Grace pose as millionaires interested in buying the townhouse of Sandra Bernhard. Meanwhile, Karen attends stepson Mason's swim meet; and Jack becomes obsessed with a Ricky Martin scooter and Britney Spears platform shoes on eBay.

Will finally works up the chutzpah to call Matthew, whom he met at Banana Republic. Though Will strikes out when he tries impersonating a sports fan for Matt's benefit, sparks still fly between the two. Meanwhile, Grace busies herself redecorating Jack's apartment; and Jack and Karen are convinced that Grace is a psycho.

Will is torn over ending his newfound relationship with Matt, a rising TV sportcaster who is extremely reluctant to let the world -- especially his macho business associates -- know about his sexual preference, so he continues to refer to Will as his 'brother.' Meanwhile as Grace does her best to help Will decide, Karen is livid when she discovers that he helped draft her husband's will, which will award much of his estate to charity.

Will chides Grace for owning an old car 'with no A/C and 'old-man stink',' so she lets him sell it. But when she decides she wants the lemon back for sentimental reasons, it proves difficult to retrieve from the quirky buyer, Sister Louise. Meanwhile, a cryptic postcard from his mother convinces Jack that he's half black. And when a fellow trophy spouse tries to steal Rosario, pool shark Karen challenges him to a game--with her trusty maid as the stakes.

Will's father George returns, harboring a spicy secret, in this intrigue-filled episode. As if sitting through 'Seussical' on a date with a Frankenstein lookalike weren't rough enough, Grace spies George at the theater--getting very cozy with a woman who isn't Will's mother. After she spills to Will, he goes into denial, refusing to deal with this revelation. But an explosion comes anyway when George's giggly mistress is indiscreet. Meanwhile, Karen and Jack plot to nail Stan, who's also suspected of adultery.

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.

Will feels the heat from his poker-playing pals when their weekly get-together is compromised by an obnoxious Grace whose ineffective gamesmanship leaves her in debt to everyone, but she begs him for another chance -- and confides her secret weapon to regain her losses. Elsewhere, Karen gloats when she and Jack convince her equally haughty and naughty rival to be her 'guinea pig' as the woman submits to experimental plastic surgery.

When Grace frets that she and Will might drift apart like their similar friends, she impulsively buys an expensive piano which she hopes will cement their mutual bond and love for music -- or at least give her an excuse to perform a lot of show tunes. Meanwhile, when Jack is dumped by his latest romantic interest, he vents his grief by writing trashy novels which instantly draw Karen's passionate attention.

Grace gives romantic advice to her slovenly new neighbor Nathan in hope of reuniting him with his girlfriend so he will move away. Meanwhile, Will and Jack are out on the town with an unwelcome chaperone: Karen's oblivious mother-in-law.

A whacked-out Grace is wracked with guilt over the passing of a high school classmate whom she once tormented, so she drags Will along to the funeral -- and gets the surprise of her life -- while Will offers a sympathetic shoulder to a handsome grieving relative. Elsewhere, an ecstatic Jack asks Karen to accompany him when he is nominated for a MAC award for lower Manhattan non-transgender equity waiver gay cabaret.

Grace hates herself for her fatal attraction to Nathan and wants to keep her embarrassing romance with him a secret; likewise, Will prefers to maintain discretion in his relationship with a much younger man. Meanwhile, Jack revels in the attention lavished on him by Grace's eccentric friend, Val.

An exasperated Grace tries to mediate between a resentful Will and her sloppy, free-spirited boyfriend Nathan when Nathan moves in while Jack is in a royal dither as he plans to finally meet his unseen father face-to-face. However, Grace grows nervous when the two polar-opposite men find some common ground and she ponders how a devoted boyfriend might affect her equally important relationship with her longtime buddy Will. After settling his father issues, Jack later gets the surprise of his life in a most unexpected fashion.

An exasperated Grace tries to mediate between a resentful Will and her sloppy, free-spirited boyfriend Nathan when Nathan moves in while Jack is in a royal dither as he plans to finally meet his unseen father face-to-face. However, Grace grows nervous when the two polar-opposite men find some common ground and she ponders how a devoted boyfriend might affect her equally important relationship with her longtime buddy Will. After settling his father issues, Jack later gets the surprise of his life in a most unexpected fashion.