Grace is about to get married, but Will talks her out of it.

Grace needs to find a new apartment, and after intially encouraging her to get her own place, Will realizes that he wants her to move in with him.

Will freaks out when Grace decides to renovate their two bathrooms into one.

Will interferes when Grace re-decorates Harlin's apartment.

Jack convinces Karen to dress up and go to the Halloween parade with him, but when Karen finds herself worshipped by all the drag queens, Jack feels left out... until he meets the Starsky to match his Hutch. Will and Grace finally learn to love Halloween when Harlin drops his two kids off with them for the night.

Karen goes on vacation so Grace hires Jack to be her assistant. Jack tells her about an affair that Will had last summer that Grace didn't know about. Grace starts worrying that Will is hiding things from her, and stalks him when he goes out to dinner with a client. It turns out that the client is Karen who is considering leaving her husband, although Will manages to talk her out of it before Grace barges in. It turns out that Grace is scared that he is going to give her some big life-changing announcement like he did in college when he came out of the closet.

Jack hasn't ever paid his taxes. Grace is suffering from a lack of interest in men and dating, and thinks it might be caused by the fact that she's having too much fun with Will.

Grace buys her work studio. Jack trains to be a masseur.

Will declares that he hates dogs, but when Grace brings home an adorable puppy, he falls in love and develops a debilitating obsession. They end up having to give the dog away to Jack.

Will and Grace eavesdrop on the couple downstairs through their heat vent.

Will never seems to get what he wants for his birthday, and this year is no exception when he gets dragged to an ice-skating show by Jack and Grace.

Will hires a cleaning lady and Grace becomes dependent on her for support while preparing for an upcoming designers' contest. Jack dates a guy he met in a bookstore, but when he lies that he's a successful lawyer, he drives the young graduate student away.

Grace's mother comes to visit and suggests that Grace marry Will. Karen is horrified when she thinks she might be pregnant, but is actually sort of sad when she realizes she isn't.

Will's estranged, older brother turns up at Jack's birthday party, and Grace tries to reunite them.

Will finds out about Grace sleeping with his brother, and although he's initially upset, he comes to terms with the fact that he really has not right to tell her who she can and can't sleep with.

Will and Grace both have a crush on their new neighbor, and can't figure out which one of them he is interested in. Karen has to fire her driver.

Jack, Grace, and Karen take Will to Vermont for the weekend to get his mind off his anniversary with his ex-boyfriend. While they're there, Grace romances an old flame and tries to hide the fling from Will. Will tries not to be jealous.

While Grace is busy at work, Will becomes friends with their new neighbor, Val, and Grace becomes jealous. Jack slaps a meter-maid and is sentenced to pick up trash.

Much to Will's embarrassment, Jack joins his gym, a place where he often conducts business with clients. He tries to tone down Jack's outrageous behavior, and when he complains to Grace that Jack is such a fag, Jack overhears him. Jack is upset, and Will realizes that he's rejecting Jack for his being different just as so many other people in his life have. When Karen has a fight with her husband, Grace suggests she go out with a girlfriend and have a good time. They both realize that Karen doesn't really have any girlfriend, so Karen comes over to Grace's place to hang out and they get drunk on tequila and bond.

A successful and very self-centered publicist hires Grace to decorate his office with the condition that Will dates him.

Grace tones down her competitiveness during game playing as Will's focus changes to winning. Karen saves a workman's life. Guest starring Tom Gallop and Leigh Allyn Baker.

After Grace temporarily gets back together with her ex-fiance, Grace and Will realize that their living together may be preventing them from finding mates. Jack marries Karen's maid Rosario so that she can stay in the country.