After a fight with her boyfriend, Grace decides to break up with him, much to Will's delight. But when she accepts his marriage proposal, Will decides to risk his friendship with Grace by telling her what he thinks.
Grace wants to move in with Will, but he encourages her to find her own apartment. He has second thoughts when she finds a place across town. Meanwhile, Jack, who is temporarily staying with Will, is driving Will crazy.
Grace decides to renovate the bathrooms, causing tension between the new roommates.
Grace gets carried away with a cowboy theme when she decorates Harlin's apartment.
Grace decorates Harlin's place in a cowboy motif; Jack decides to pursue a singing career.
Jack dresses up as 'Hutch', and Karen as a cat woman, for Halloween; Will and Grace go trick or treating in the apartment building with Harlan's kids.
Grace gets paranoid that Will is keeping secrets from her after Jack tells her that Will had an affair with a client.
Grace blames her lack of interest in dating on her relationship with Will.
Grace decides that her lack of interest in dating is a result of her friendship with Will; Jack asks for Will's help when the IRS begins to inspect him.
Grace gets the chance to buy her office space and asks Will for advice; Jack decides to become a massage therapist and practices his technique on Karen.
Will becomes obsessed with a dog that Grace adopts.
Grace brings home a dog against Will's wishes, but he quickly becomes overly attached to it.
Will and Grace discover that they can eavesdrop on the soap opera-like lives of their neighbors by listening through a vent in the apartment. They get so absorbed that they become oblivious to Jack.
In an effort to help Grace and Jack bond, Will agrees to go to an ice-skating competition for his birthday.
Will hires a maid for the apartment; Jack poses as lawyer to impress a cute guy.
Grace is panicked over an upcoming design competition, which she always loses. To help with the apartment chores, Will hires a maid, but she winds up helping Grace with her designs instead of keeping the apartment in order. Meanwhile, Jack poses as a successful lawyer to impress a cute guy.
Grace's outlandish mother visits and suggests that Grace should marry Will. Also, Karen thinks she's pregnant.
Grace surprises Will by inviting his older brother to Jack's birthday party.
Will's estranged brother Sam shows up at a surprise birthday party for Jack; Karen and jack go shopping and run into a salesperson that had snubbed Jack.
Grace tells resentful Will of her romance with Sam; Karen hires Jack as assistant.
Grace tells Will about her romance with his brother Sam; Karen hires Jack as her personal assistant.
Both Will and Grace are interested in dating a new neighbor, but they can't figure out if he's straight or gay.
The gang goes up to a cabin in the woods to help take Will's mind off of the anniversary of his breakup with Michael. While there, Grace runs into an old flame and tries to hide her fling from Will.
When Grace becomes very busy, Will starts spending time with a new friend, Val. That leads Grace to worry that she will be replaced as Will's best friend. Also, Jack is sentenced to pick up trash after slapping a meter maid.
When Jack joins his gym, Will becomes embarrassed by Jack's flamboyant behavior.
A publicist hires Grace on the condition that she sets him up with Will; Jack shows Will how to kiss someone he finds unattractive.
Rob and Ellen admit that they do not like playing games with Will and Grace because Grace is so competitive; Karen saves a man using CPR.
Roommates rethink their living arrangement; Jack weds Karen's maid.
Will and Grace rethink their living arrangement; Jack marries Rosario.
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