Will (Eric McCormack) finally returns from his Caribbean working vacation and tries to help a confused Grace decide between her two sub-par boyfriends but he gets a rude awakening when he jealously discovers that Jack (Sean Hayes) has insinuated himself with Grace in his absence - making him feel like odd man out.

Will's (Eric McCormack) apartment resembles a disheveled boarding house when a rattled Grace (Debra Messing) seeks refuge after someone tries to break into her apartment, but her needy presence - combined with Jack (Sean Hayes) and his latest entourage - force the longsuffering Will to demand that one of them must go.

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.

Grace's (Debra Messing) delight in having a bright intern (guest star Natasha Lyonne, "Slums of Beverly Hills") whom she can mentor turns into horror when the young woman re-makes herself into the spitting image of sassy, brassy Karen (Megan Mullally) - and that's at least one too many Karens to handle.

Grace (Debra Messing) has made up her mind to break up with Ben (guest star Gregory Hines) because she's convinced their relationship is going nowhere - but his charm and refusal to call it quits tempt her to reconsider.

Grace (Debra Messing) rejects an ex-boyfriend's suggestion that she participate with him and his girlfriend in a romantic escapade but when she confides in Will (Eric McCormack) and Karen (Megan Mullally) - who falls down laughing at the prospect - the conservative Grace considers throwing caution to the wind.

Will (Eric McCormack) reluctantly decides to use a birthday gift certificate from Grace (Debra Messing) to consult a psychic about his future and encounters an absent-minded fortune teller (Emmy-winning guest star Camryn Manheim, "The Practice") whose frighteningly personal predictions leave him reeling.

In a flashback to Thanksgiving 1985, coed Grace (Debra Messing) invites her college boyfriend Will (Eric McCormack) home to meet her family, but their romantic relationship swerves dramatically when a conflicted Will phones a teenaged Jack (Sean Hayes) for some crucial advice. Part 1 of 2.

In a flashback to Thanksgiving 1985, coed Grace (Debra Messing) invites her college boyfriend Will (Eric McCormack) home to meet her family, but their romantic relationship swerves dramatically when a conflicted Will phones a teenaged Jack (Sean Hayes) for some crucial advice. Part 2 of 2.

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.

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.

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 a fake offer - but their ploy fizzles when she accepts their offer.

A sports-challenged Will (Eric McCormack) tries to impress his new friend Matt (guest star Patrick Dempsey, "Once and Again," "Crime and Punishment") - a sportscaster - with his athletic skills by checking into a batting cage but it takes Grace (Debra Messing) to show him how to improve his swing.

Will (Eric McCormack) is torn over ending his newfound relationship with Matt (guest star Patrick Dempsey), 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."

Grace dispatches Will to sell her dearly departed uncle's jalopy but after he makes the sale to an enterprising nun (guest star Ellen DeGeneres, "Ellen"), 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.

Grace (Debra Messing) is apoplectic when she catches Will's (Eric McCormack) philandering father (guest star and Oscar-winning director Sydney Pollack) on the arm of a glamorous stranger (guest star Lesley Ann Warren, "Victor/Victoria") but she gets even more worked up when she tells Will - and he's happy living with denial. Part 1 of 2.

Grace (Debra Messing) is apoplectic when she catches Will's (Eric McCormack) philandering father (guest star and Oscar-winning director Sydney Pollack) on the arm of a glamorous stranger (guest star Lesley Ann Warren, "Victor/Victoria") but she gets even more worked up when she tells Will - and he's happy living with denial. Part 2 of 2.

Grace is smitten when she meets Sumner (guest star Paul Satterfield), the charming and handsome nephew of Karen (Megan Mullally), but Grace's attempts to arrange a date are constantly thwarted when Karen conjures up a litany of lies to dissuade her.

Will (Eric McCormack) feels the heat from his poker-playing pals when their weekly get-together is compromised by an obnoxious Grace (Debra Messing) 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.

When Grace (Debra Messing) frets that she and Will (Eric McCormack) 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.

Grace's (Debra Messing) new neighbor is a slovenly lout whose disheveled lifestyle and grungy habits put him at odds with her well-ordered world - and her only hope to dislodge Pigpen is to provide him with enough romantic advice to reunite him with his long-suffering girlfriend.

A whacked-out Grace (Debra Messing) is wracked with guilt over the death of a high school classmate whom she once tormented, so she drags Will (Eric McCormack) along to the funeral - and gets the surprise of her life - while Will offers a sympathetic shoulder to a handsome grieving relative.

Grace (Debra Messing) hates herself for her fatal attraction to a boorish neighbor (Oscar-nominated guest star Woody Harrelson) and wants to keep her newborn romance with him a secret; likewise, Will (Eric McCormack) prefers to maintain discretion in his relationship with a much younger man.

An exasperated Grace (Debra Messing) tries to mediate between a resentful Will (Eric McCormack) and her sloppy, free-spirited boyfriend Nathan when Nathan moves in while Jack (Sean Hayes) is in a royal dither as he plans to finally meet his unseen father face-to-face. Part 1 of 2.

An exasperated Grace (Debra Messing) tries to mediate between a resentful Will (Eric McCormack) and her sloppy, free-spirited boyfriend Nathan when Nathan moves in while Jack (Sean Hayes) is in a royal dither as he plans to finally meet his unseen father face-to-face. Part 2 of 2.