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Jack reconnects with his teenage son, Karen faces upheaval in her extravagant lifestyle, and Will and Grace navigate their evolving friendship amid career and dating mishaps. Guest stars like Cher, Sandra Bernhard, and Woody Harrelson bring standout moments in this sharp and heartfelt season.
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Episode 1
The Third Wheel Gets the Grace
September 27, 2001
Will returns from vacation to discover that Grace's romantic relationship with neighbor Nathan is humming along. Nathan feels neglected when Will and Grace resume their chummy friendship, complete with their own private language and code. Meanwhile, Jack proudly takes his new-found son Elliot shopping for school at Barney's while Rosario and Karen each cruise the merchandise looking for the perfect "anniversary gift".

Episode 2
Past and Presents
October 4, 2001
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.

Episode 3
Crouching Father, Hidden Husband
October 11, 2001
Jack is puffed up with paternal pride as he escorts his long-lost teenaged son Elliot to a junior high school dance but not before he coerces Grace into posing as Elliot's date â€" which only revives her own tortured memories of rejection from school dances many years before. Elsewhere, Karen has great fun at her lawyer Will's expense when she continues to capriciously summon him for bogus ""emergencies"" â€" that is, until she really needs him.