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.

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.

When Grace moves in with Will, 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.

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.

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.

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.

Grace (Debra Messing) blames her relationship with Will (Eric McCormack) as the reason for her lack of interest in dating and decides they can no longer have fun together. Meanwhile, Jack (Sean Hayes) enlists Will's help when the IRS catches up with him.

Grace (Debra Messing) has the opportunity to buy the studio that serves as her office space and turns to Will (Eric McCormack) for first-time buyer advice. However, Will's negotiating tactics lead Grace to believe that Will thinks she is incapable of closing the deal and she sets out to prove him wrong.

Will (Eric McCormack) balks at first when Grace (Debra Messing) decides to adopt a dog, but the winsome pooch soon becomes his obsession, until Grace coaxes him to let Jack (Sean Hayes) and Karen (Megan Mullally) puppy-sit, with surprising results.

Will (Eric McCormack) and Grace (Debra Messing) become hooked on a real-life soap opera unfolding in their neighbors' apartment when they begin eavesdropping through the new heating vent in their floor.

It's Will's (Eric McCormack) birthday and all he wants is a nice, quiet dinner with his two best friends, Grace (Debra Messing) and Jack. When Jack and Grace discover they share a passion for figure skating, they surprise Will with tickets for 'Champions on Ice' and Karen reluctantly joins the special evening.

Will (Eric McCormack) hires a cleaning lady (guest star Wendie Jo Sperber) to 'rescue' his designing roommate Grace (Debra Messing) from the creative chaos that litters their apartment, and while preparing for an annual decorators' contest, Grace develops a dependency on her maid and can't create without her.

Grace's (Debra Messing) visiting mom, Bobbi Adler (guest star Debbie Reynolds), a would-be star whose propensity for breaking out into show tunes and impressions dismays her daughter - and delights Will (Eric McCormack), Jack (Sean Hayes) and Karen (Megan Mullally).

A 'surprise' birthday party for Jack (Sean Hayes) astounds Will (Eric McCormack) when his estranged older brother Sam (guest star John Slattery) turns up at the fete at Grace's invitation. Not only do sparks fly between the brothers, but electricity of a different sort crackles between Grace and Sam.

A wary Grace (Debra Messing) tells Will (Eric McCormack) of her romance with his brother, Sam (guest star John Slattery), and unleashes an avalanche of resentment.

Stunned to find they have a 'date' with the same guy, Will (Eric McCormack) and Grace (Debra Messing) compete for the affections of a handsome, charming new neighbor (guest star David Newsom, 'Homefront') at dinner, and even Jack's 'gaydar' can't pick up his preference.

The gang retreats to a cabin in Vermont for the weekend, where Grace (Debra Messing) rekindles romance with an old flame (guest star David Sutcliffe) and tries to hide the fling from Will (Eric McCormack), who's pining on the eve of his would-be anniversary.

Will (Eric McCormack) finds a 'substitute Grace' in Val, a new neighbor who is available for plans with Will while Grace (Debra Messing) is consumed with work. As Will and Val continue to spend more time together, Grace fears that she has been replaced.

Will (Eric McCormack) invites Jack (Sean Hayes) to his gym on a 'buddy pass,' but when he expresses his embarrassment to Grace (Debra Messing) over his buddy's gay behavior, Jack overhears the comments and looks to set him straight about prejudice.

Miguel Ferrer ('Lateline') guest-stars as Nathan, a successful New York publicist who hires Grace to decorate his office on the condition that Will agrees to date him. Meanwhile, Jack (Sean Hayes) uses Karen (Megan Mullally) to teach Will how to kiss someone he finds unattractive.

When Rob (guest star Tom Gallop) and Ellen (guest star Leigh-Allyn Baker) admit that they don't have fun playing games with Will (Eric McCormack) and Grace (Debra Messing) because of Grace's competitive nature, Grace works to change her image.

After Grace (Debra Messing) contemplates a renewed relationship with her ex-fiancée, Danny (guest star Tom Verica, NBC's 'Providence'), she and Will (Eric McCormack) re-think their living situation.