Will and Jack wake up naked in a bed together after a night of drinking. Grace worries about Leo's potential infidelity when she finds out that one of the doctors in his program has a big thing for him through a love letter.
Grace is flustered to discover that Leo's ex is also the only woman that Will has ever been with.
When Grace discovers Karen's anonymosity towards Leo, she tries to think of a way to bring them together. Will tricks Jack into tagging along on a trip to help raise Will's mother's spirits.
Jack tries to help James Earl Jones with his off-Broadway performance.
Leo looks to Will for a revival of his love for New York, but Will's New York isn't exactly what Leo had in mind. Jack trains with Karen for a gay spelling bee.
While out wheeling his mother around, Will meets an attractive man also wheeling someone around and continues their meetings in the hopes of something happening between them. Karen's hunt for Lorriane produces Lorraine's father.
Jack decides he wants to be a nurse and asks for Will to believe in him. Karen's annual physical takes an odd turn when her doctor turns out to be more than a little odd.
Will tries to get Grace to extend her visit back to New York. Jack has trouble with his new nursing teacher and Karen takes care of her, but Jack realizes that he really belongs in the school.
Will tries to help Grace's downtrodden spirits by taking her out on his dinner date, but when his man doesn't show, he also feels depressed. Grace finds comfort in a man from her past while Will finds an ego boost from a female patron. While out with Jack, Karen's path crosses with archrival Candice Bergen.
Will skips Grace's Christmas party to wait in line for Barry Manilow tickets. Grace catches him and he convinces her to take his place while he takes a bathroom break. Grace learns that her mother broke off plans to have dinner with Jack and Karen.
Grace's tough talk with her visiting sister brings about a metamorphosis in character that leaves Grace feeling unsure about the change. Lyle continues to doggedly pursue Karen. When Lorraine objects to the coupling, Karen's interest grows.
Will is accused of having a sugar daddy when he gains the attention of a rich older man who showers him with gifts. Grace's protest of a noodle restaurant falls on her friend's deaf ears.
A new client develops feelings for Jack and Will tries to do anything he can to get Jack to agree to a date. Grace and Karen find a hidden stockpile of money at Leo's cabin.
Karen gets Grace to fix up her mother's apartment on a very tight budget. Will takes a cooking class but is disappointed when he turns out to be the only single participant.
Will and Grace begin a business venture selling apartments; Jack runs into his former acting mentor, Zandra; Karen and Lyle (John Cleese) try to renew romance.
Will and Grace decide to partner up with Will purchasing old apartments and Grace renovating them for resale. Karen's time with Lyle hits a snag when Lorraine reappears.
Will and Grace try to break up Jack and Stuart (Dave Foley) so they can sell the apartment for a higher price; Karen demands that Lyle (John Cleese) discipline his daughter (Minnie Driver).
Grace and Will try to separate Jack and Stuart so they can get their hands on the apartment to sell to a higher bidder. Karen's request of Lyle to reign in Lorraine interferes with their relationship.
Will and Grace try to take on the competition in the form of a lesbian pair of apartment flippers and try to break them up. Karen wonders about her engagement and seeks answers from beyond with the help of John Edwards.
Jack spies Stuart with another man at the movies. Will's attempt at teaching Karen to drive lands him in traffic court.
Will follows Grace's advice to play hard to get and the tactic backfires on him. Jack and Karen fret over losing their favorite television shows.
Will frets over Grace's reaction to his new boyfriend. Jack holds auditions for Karen's replacement when she says they won't spend time together after she gets married.
Tina asks Will to find out if there is another woman in his life. Jack encourages his son to try out for the cheerleading team.
Jack asks for Will's help in writing his commencement speech.
Karen moves her wedding to Las Vegas, where Jennifer Lopez agrees to sing at the ceremony.
Karen moves her wedding to Las Vegas, where Jennifer Lopez agrees to sing at the ceremony.
Karen and Lyle decide to wed in Las Vegas. Jennifer Lopez signs on to sing at the wedding. Leo tries to return to Grace from Cambodia.
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