In this season opener, Grace (Debra Messing) wants to prove that she's not completely dependent upon Will (Eric McCormack) by moving to the apartment across the hall.
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Grace (Debra Messing) discovers that Will (Eric McCormack) has certain perks in his apartment, such as a working fireplace, that other tenants, like herself, don't have.
A flattering newspaper photo gains Grace the attention of an old crush (Scott Patterson) who was never one to keep abreast of her before. Meanwhile, Jack is destroyed to learn that Will had a thing with his former fling (Anthony DeSantis).
Grace hits the roof when her matchmaking mom (Debbie Reynolds) visits with yet another man in tow. Unfortunately, he's perfect...for Will. Meanwhile, Jack and Rosario meet with an INS agent who's well acquainted with Jack's past.
Grace teaches Karen about budgeting by taking her outlet shopping, while Will sells himself short to land a fickle, filthy rich client (Gary Grubbs). But when the bottom drops out, a vindicated Grace feels bad about coming out on top.
After closing his office, Will accepts a dare to work as one of Jack's cater-waiters. Meanwhile, Grace catches Karen at work - in an adult film.
Jack tries to come out to his mom (Veronica Cartwright), who shows up for Thanksgiving dinner at Will's armed with a secret of her own. But before any secrets are spilled, Karen and Grace duke it out over their make-believe ex-lover, namely Jack.
Grace enlists an out-of-practice Will to sue one of her clients (Gregory Hines), a hotshot lawyer who kills her case, but saves Will's career. Meanwhile, Jack and Karen turn a training film set into an adult entertainment experience.
Bored with Rob and Ellen's low-rent tastes, Grace and Will dump them for a pair of highbrow downtowners (Tamlyn Tomita, Steve Valentine). Meanwhile, Karen helps Jack face his painful past during a trip to her kid's grade school.
Will's (Eric McCormack) new boss (guest star Gregory Hines) gives him an ultimatum - he has until Friday to bring in a major new client to the firm or lose his job.
Will's sexy dreams about Grace land him in therapy and send her on a couch trip with his hunky shrink (Markus Flanagan). Meanwhile, Jack and Karen clash over her treatment of Rosario.
Will and Grace are forced to pose as married at his father's awards dinner; Jack's blind date may have a surprising connection to his past.
Will and Jack appear on Today to protest NBC for yanking a gay kiss from a sitcom episode; Grace seeks Karen's advice on dumping a weirdo beau. Al Roker guest stars as himself.
When Will (Eric McCormack) is set up on a blind date (guest star Michael E. Rodgers) by his boss (guest star Gregory Hines), he has internal debates on whether or not to go.
When an old school chum (Megyn Price) asks Will to father her child, a jealous Grace tries to thwart her baby-making plans.
Will has designs on Grace's newest interior-decorating client - his ex-boyfriend (Chris Potter); Karen tries taking her "career" more seriously.
When Karen's husband, Stan, suffers a heart attack, the gang takes bets on whom the sassy socialite will turn to for emotional support.
As the gang plunges into charity work, Will and Grace direct a kids' play, while Jack infuriates Karen by giving away her favorite pair of pumps.
When two pals ask Will and Grace to be the best man and maid of honor at their wedding, Grace's sexy past with the groom is exposed.
Grace befriends a sassy kleptomaniac (Molly Shannon); Jack has a crush on the leader of a group of "ex-gays" (Neil Patrick Harris).
Will and Grace are alarmed when the friendship of two bickering oldsters mirrors their own; Ben (Gregory Hines) impresses Jack and Karen with his hidden talents.
A catty socialite (Joan Collins) of Karen's acquaintance vies with Grace for a client; Jack tries marketing an odd invention.
After his legal tussle with Karen, Jack moves in with Will, who is reeling from reversals in his career and love life.
Unknown to Will (Eric McCormack), Grace (Debra Messing) has a romantic dalliance with his boss Ben (guest star Gregory Hines).