Nathan feels left out when Will returns from vacation and resumes his chummy friendship with Grace. Meanwhile, Jack takes his son back-to-school shopping at Barney's.
Will's firm hires a childhood bully of his; Grace gets upset that Karen gives Nathan a nicer gift that hers.
Grace agrees to be Jack's son's date to a school dance.
When Stan is arrested for tax evasion, Grace provides emotional support to Karen by moving into her deluxe apartment. Grace has no trouble adjusting to the good life.
Jack sets up a "date" between his female supervisor and Will in a sneaky effort to get a night off from work.
Nathan proposes to Grace but she recoils since the moment doesn't fit with the fantasy she's had since she was a child.
Will, Jack and Karen try to cheer Grace, who is depressed after losing Nathan.
Will, Jack, and Karen try to make Grace feel better after her breakup with Nathan.
Will and Grace end up as political adversaries when they back opposing candidates in a mayoral election.
On Thanksgiving Day, the friends band together for a motor tour of their dysfunctional families.
On Thanksgiving Day, the friends band together for a motor tour of their dysfunctional families.
On Thanksgiving Day, the friends band together for a motor tour of their dysfunctional families.
On Thanksgiving Day, Will and Grace join Jack and Karen in a motor tour of their respective dysfunctional families. Stops include Karen's husband in jail, Grace's mother, and Jack's stepfather. Rosario, meanwhile, is at Will's place, "watching" the turkey.
On Thanksgiving Day, Will and Grace join Jack and Karen in a motor tour of their respective dysfunctional families. Stops include Will's family, Grace's mother, and Jack's stepfather. Rosario, meanwhile, is at Will's place, eating all the turkey.
Will recognizes a guy at the gym who looks familiar, but he can't place him. Also, Grace tries to get a loan to expand her business and winds up asking Karen for the money.
Grace spends the Christmas season as the holiday window dresser for Barney's.
Grace plots to break Will's father away from his mistress my pushing her towards another man.
Grace visits Karen's incarcerated husband and re-unites with a high school flame, also doing time.
Will and Grace attend the wedding of Grace's ex and she tells the bride about all the groom's faults. Also, Elliot's mother tells Jack never to see him again.
Jack tries out for a spot in a gay men's chorus and his biggest competition is a man Jack thinks isn't really gay, so he asks Grace to seduce him. Also, at a party, Karen tries to pass off Will as her lover when she thinks people are pitying her.
Will and Grace illegally sublet their old flat to finance their new large apartment.
To finance their new larger apartment, Will and Grace illegally sublet their old place. Also, for her birthday, Jack films a documentary about Karen's life, complete with her estranged mother.
Will and Grace move into their dream apartment but find that they miss their old one.
After moving into their new roomy apartment, Will and Grace realize that they miss their smaller old one. Unfortunately, their friends are subletting their old place. Also, Jack tries to reconcile Karen with her mother.
Will gives his recently reconciled parents a cruise trip for their anniversary.
Grace inadvertently beheads Will's Garden gnome.
When Jack works instead of taking his son to a basketball tournament, he misses out on his son's first kiss.
Grace helps plan a wedding for Will's visiting friends after the bride-to-be gets sick.
A closeted gay detective pretends to help Will search for his stolen computer so he can "date" Will. Also, Val - the psycho neighbor - opens a rival design business.
Will takes Grace to pose for a photographer who proves to have a flair for the eccentric.
Aware that time is passing, Will asks Grace to become the mother of his baby.
Will asks Grace to be the mother of his baby.
Will and Grace vacillate on artificial or natural means of conceiving a baby; Jack receives career advice from his show-business idol, Cher.
Will and Grace vacillate on artificial or natural means of conceiving a baby; Jack receives career advice from his show-business idol, Cher.
Will and Grace vacillate on artificial or natural means of conceiving a baby; Jack receives career advice from his show-business idol, Cher.
Will and Grace plan to use artificial insemination to impregnate Grace, but when Will's sperm ends up all over his neighbor's floor, they try to resort to natural means.
Part 2 of the season finale in which Will and Grace try to conceive a baby and Jack receives career advice from his idol Cher.
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