Episode list

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; and 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.

Will gets upset when his new boyfriend refuses to recognize him as his boyfriend when they're in public and introduces him as his brother. Grace tells him he should dump him but Will finds it difficult to do that. And Karen discovers that Stan is giving a portion of his estate to charity in his will.

Jack receives a letter that indicates he is black. Grace inherits an old a car from a deceased uncle. She sells the the car that she believes to be a lemon to a nun. Meanwhile, Karen discovers that Rosario is moonlighting for Beverly Leslie. Grace realizes that she should have kept the car and tries to buy it back.

Grace is apoplectic when she catches Will's philandering father on the arm of a glamorous stranger.

Will must face the truth about his father's affair.

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

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.

Grace fears Will is pulling away, so she buys a piano for them to bond over. Meanwhile, Jack is depressed over a recent breakup and channels his energy into writing romance novels, which Karen quickly becomes addicted to.

Grace's (Debra Messing) new neighbor, guest star Woody Harrelson, is a slovenly lout whose disheveled lifestyle and grungy habits put him at odds with her well-ordered world.

Will and Grace attend a funeral so that Grace can apologize for belittling a former classmate years ago. Also Jack gets ready for a gay cabaret award event with the help of Karen.

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.

Grace struggles trying to get Nathan and Will to get along, while Jack prepares to meet his birth father.

Will and Grace's relationship threatens the one she has with Nathan. Still heartbroken over the news about his real father, Jack also learns that he himself is a daddy, and not in the way he'd like.

Nathan (Woody Harrelson) feels like the third wheel when Will returns from his vacation and resumes his friendship with Grace. Jack takes Elliot shopping for school clothes.

Will's former bully from school is hired as a new attorney at his firm. Grace is upset that Karen's birthday gift to Nathan is better than hers.

Karen cries wolf to Will too many times for his own liking, whilst Grace lends a helping hand to a dateless Elliot for his prom.

Jack introduces Will to acting coach Zandra for help with a fear, and Grace stays at Karen's while Stan's in prison.

Jack tries to appease his new boss by setting her up with Will, and jealousy and fear complicate Grace and Nathan's relationship.

Nathan proposes to Grace but not in the way she was hoping to be. So he tries to do it again but things don't come out as she hoped.

Will, Jack and Karen try to console a devastated Grace after her break up from Nathan

It's election time and Will and Grace are supporting different mayoral candidates cause one is gay and the other is Jewish.

Rather than be apart on Thanksgiving Day, Will and Grace join Jack and Karenfor a festive holiday motor tour of their respective dysfunctional families.

When Will, Grace, Jack, and Karen want to spend Thanksgiving together. But they each have to visit someone or go to another Thanksgiving dinner. So Will comes up with the plan to visit each place for one hour at a time. But each visit leaves them reeling and leaves them unable to enjoy their own celebration.

Will has old and new boyfriend issues at the gym, and a business proposal causes problems between Grace and Karen.

Grace has found out about Robert. Will doesn't want to introduce Robert to Grace, but Grace invites Robert to dinner and he accepts. Jack names Karen as his assistant on a designer job.