Grace is dating her ex again, which Will thinks is wrong but tries not to interfere. Karen's maid Rosario risks being deported, so Jack agrees to marry her.

Rob and Ellen want to stop having game nights with Will and Grace due to Grace's poor behavior when she plays.

An arrogant and overbearing client lets Grace design his apartment, but only on the condition that she gets Will to go on a date with him.

Will takes Jack to his gym, but is embarrassed by Jack's overly gay behavior.

When Grace is too busy with work to spend time with Will, Will builds a friendship with Val, a neighbor.

Will, Grace, Jack, and Karen spend a weekend together in a cabin in Vermont.

Will and Grace get a surprise when they find they both have what they think is a date with the same guy.

Will is not happy when he learns that Grace and his brother Sam spent the night together. Karen helps Jack accept that he has turned 30.

Grace runs into Will's estranged brother, sparking tension when she invites him to Jack's birthday party in order to get him and Will speaking again.

Grace's interfering mother visits, and Grace realizes she may be becoming just like her.

Will hires a maid that Grace initially doesn't want, but ends up being reliant on for her decorating work.

Will gets taken to Champions on Ice for his birthday, even though he's just wanting to spend a quiet evening at home.

Will and Grace become addicted to a real life soap opera that they can hear through a vent in their floor. Jack puts on a play that he bases on his friends.

Will finds himself dealing with dog issues when Grace brings one home.

Will assists Grace in buying her office space, but Grace gets insulted at his way of doing things. Karen helps Jack learn massage.

Grace thinks her friendship with Will is keeping her from having fun and stops doing things with him. Will has to help Jack when the IRS comes after him.

Grace gets paranoid after Will takes on Karen as a client and refuses to tell her due to lawyer confidentiality.

Will and Grace get stuck taking Harlin's kids trick or treating.

Grace decorates Harlin's apartment in an extreme cowboy fashion, which Will finds to be too excessive. Jack decides on a career in singing and gets Karen to help him.

Grace has issues with her tiny bathroom after moving in with Will, who has a large one.

Karen and Jack first meet. Will has to decide on letting Grace move into an apartment in a bad neighborhood, or move in with him. Complicating things is Jack, who already lives there.

Will tries to be supportive of Grace's choice to marry her boyfriend. He eventually tells her that she's making a mistake, even though it may jeopardize their friendship. Jack is supposed to move in with Will.