First Lady of Jamaica

When Grace (Debra Messing) gets a marriage proposal, Will (Eric McCormack) risks their friendship by telling her what he thinks.

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.

Will (Eric McCormack) faces the big issues when Grace (Debra Messing) moves in and wants to knock down the bathroom walls.

Grace's (Debra Messing) decorating job on Harlin's (Gary Grubbs) place embarrasses Will (Eric McCormack), who then makes an even bigger mess.

Jack and Karen (Sean Hayes, Megan Mullally) head out to party, while Will and Grace (Eric McCormack, Debra Messing) go trick-or-treating with Harlan's (Gary Grubbs) kids.

Grace worries that Will is keeping secrets from her after Jack discloses Will's past affair with a client.

Grace (Debra Messing) blames Will (Eric McCormack) for her lack of a social life and decides that they can no longer have fun.

Grace (Debra Messing) seeks Will's (Eric McCormack) advice on buying a studio, then sets out to prove she can make the deal.

Will (Eric McCormack) develops a dog obsession after Grace (Debra Messing) brings home a puppy, forcing her to take action.

Will and Grace (Eric McCormack, Debra Messing) eavesdrop on the couple downstairs (guest stars Tom Sullivan, Corinne Bohrer), who are involved in a marital conflict.

Jack and Grace (Sean Hayes, Debra Messing) surprise Will (Eric McCormack) on his birthday with tickets to an ice-skating show with Rudy Galindo (as himself). With Megan Mullally.

Will (Eric McCormack) hires a cleaning lady (guest star Wendie Jo Sperber) to help Grace (Debra Messing) with her preparations for an upcoming decorators' contest. With Sean Hayes and guest star Raphael Sbarge.

Grace (Debra Messing) gets a visit from her mother (guest star Debbie Reynolds), who wreaks havoc by suggesting that she marry Will (Eric McCormack).

Will's (Eric McCormack) estranged, older brother (guest star John Slattery) turns up at Jack's (Sean Hayes) birthday party; Karen (Megan Mullally) shops with Jack. With Debra Messing.

Grace (Debra Messing) tells Will (Eric McCormack) about her romance with his brother (guest star John Slattery); Karen (Megan Mullally) helps Jack (Sean Hayes) deal with turning 30.

Will and Grace (Eric McCormack, Debra Messing) compete for the affections of their new neighbor (guest star David Newsom). With Megan Mullally.

Grace (Debra Messing) romances an old flame (guest star David Sutcliffe) while in Vermont and tries to hide the fling from Will (Eric McCormack). Tom Bosley also guest stars.

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 learns a lesson about prejudice from Jack; Karen tells Grace about her rocky marriage.

A successful publicist (guest star Miguel Ferrer) hires Grace (Debra Messing) to decorate his office with the condition that Will (Eric McCormack) dates him.

Grace tones down her competitiveness during game playing, while Will's focus changes to winning; Karen saves a workman.

Grace and Will (Debra Messing, Eric McCormack) rethink their living arrangement; Jack (Sean Hayes) agrees to marry Karen's (Megan Mullally) maid (guest star Shelley Morrison).