Will Truman (Eric McCormack), a handsome, successful Manhattan lawyer, and Grace Adler (Debra Messing), a beautiful, self-employed interior designer, are best friends. In fact, they're absolutely perfect for each other -- except that Will just happens to be gay. When Grace receives an unexpected marriage proposal from her boyfriend, Will tries to be supportive of her decision but finally tells her that she's making a mistake, even though he's putting their friendship at risk. The situation is complicated by interference from Grace's socialite assistant, Karen Walker (Megan Mullally), and Will's outrageous friend, Jack McFarland (Sean Hayes).

Will (Eric McCormack) must decide whether to support Grace's (Debra Messing) independence by encouraging her to take an apartment across town or selfishly keep her close by inviting her to share his living space. The decision may be made easier, however, by the nagging presence of Will's current roommate, Jack (Sean Hayes), and his parrot, Guapo. Meanwhile, Karen (Megan Mullally) and Jack meet for the first time and find each other to be fabulous. Gary Grubbs also stars.

When Grace (Debra Messing) moves in with Will (Eric McCormack), she complains that the guest bathroom is too small and suggests knocking the common wall down to create one big master bathroom, which results in Will having to confront his own issues on change and his ability to have a successful relationship. Meanwhile, Jack (Sean Hayes) and Karen (Megan Mullally) bear the brunt of Will and Grace's displaced anger.

When Grace (Debra Messing) decorates Harlin's (Gary Grubbs) apartment, she gets carried away with a cowboy theme. Will (Eric McCormack) is both shocked and embarrassed by the cowboy chic and makes an even greater mess of the situation. Meanwhile, Jack (Sean Hayes) decides to embark on a singing career - with a little help from Karen (Megan Mullally).

On All Hallows Eve, Jack (Sean Hayes) is dressed as David 'Hutch' Soul (of 'Starsky and Hutch') while Karen (Megan Mullally) is costumed as a cat woman for a night in the Village filled with drag queens and a few surprises. Meanwhile, Will (Eric McCormack) and Grace (Debra Messing) go trick-or-treating in the apartment building while babysitting Harlan's (Gary Grubbs) two young kids (guest stars Reiley McClendon and Jorden Ashley) who are dressed as Buzzy Wuzzy and Richard Nixon.

When Jack (Sean Hayes) reveals to Grace (Debra Messing) that Will (Eric McCormack) once had an affair with a 'client,' she becomes paranoid that Will is keeping secrets from her. Her suspicions continue to grow when Will meets Karen (Megan Mullally) for a discreet meeting to discuss her legal problems and will only tell Grace he's meeting with a client.