Grace soon becomes dependent on April's odd brand of moral support, frustrating Will. When Grace nears a nervous breakdown during a design competition, Will hires a cleaning lady named April to organize the apartment. Grace and Jack find a mutual interest in figure skating. It's Will's birthday, and everyone goes to see Champions on Ice-even though Will doesn't want to (but pretends that he is okay). Jack writes and performs a play that expresses his dismay over the fact that Will and Grace are ignoring him. Will and Grace find entertainment in listening to the conversations through their heating vent. Meanwhile, Karen and Jack become the puppy's dogsitters, and Karen has some fun by thinning Grace's closet of outfits she deems ugly. Though Will initially hates the idea, he soon becomes obsessed with the puppy, and Grace realizes that he is lonely for companionship.
Grace feels left out when all of her friends talk about their dogs, so she adopts an adorable Yellow Lab puppy. Jack begins a career in massage therapy, taking on Karen as his first client. They end up competing to see who can get the lowest price from the owner. Grace asks for Will's help in buying the studio that serves as her office space. Jack faces trouble when the IRS catches up to him regarding his tax evasion. Grace fears that Will is the reason that she has no interest in dating men. Karen privately hires Will when she begins to consider divorcing her husband Stanley, and her insistence on secrecy only makes Grace more paranoid. Grace brags that she and Will are the best of friends, with no secrets from each other-but when Jack reveals that Will briefly had an affair that Grace didn't know about, she becomes fearful that he might be hiding things from her. Jack and Karen dress up and spend a night on the town, and Karen becomes very popular with some drag queens. On Halloween, Will and Grace plan to ignore the holiday-but they are forced to baby-sit Harlin's two children, and eventually get into the spirit of the evening. Jack begins his singing career with his first show of Just Jack. Grace designs a room for Will's boss, Harlin, which Will dislikes. Meanwhile, Jack needs help working on his resume, and Karen reluctantly takes on more responsibility in Grace's office. The change leads to Will revealing his fears about why his relationships end in failure.
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Will dislikes the idea, but forces himself to agree to prove that he knows how to compromise. Grace makes plans to create one large bathroom out of her and Will's individual spaces in the apartment. Will's friend Jack meets Grace's assistant Karen. First he dismisses her idea of living together, but later agrees. With nowhere to stay, Grace turns to Will for shelter.
Will advises Grace against marrying Danny and she freaks out. Grace gets an unexpected marriage proposal and her best friend Will deals with his own feelings about her proposal. See also: List of Will & Grace episodes No.
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