Despite her moving out (to across the hall), Will still feels that Grace clings to him, so she asserts her independence by having a dinner party without him. Meanwhile, to keep the INS at bay, Jack is forced to move in with Rosario.

24. Election

When Grace feels that Will is abusing his power as president of the tenant's association, she runs against him. Karen tries to buy back Jack's forgiveness when she lets his beloved bird, Guapo, fly out the window.

25. Das Boob

When a newspaper photograph makes Grace look more "endowed" than she actually is, she uses it to her advantage when meeting a former high school heartthrob; Jack is devasted when he learns that Will had a fling with Walter, "the love of my life"

26. Whose Mom is It Anyway?

Grace is jealous when her mother stops match making for her, and instead sets Will up; Jack must convince an INS agent (who he dated once) that he and Rosario are happily married.

27. Polk Defeats Truman

When his work for Harlan takes up all his time, Will drops all his other legal clients; a decision that later bites him you-know-where. Meanwhile Grace tries to teach Karen how to live on a budget.

28. To Serve and Disinfect

An unemployed Will agrees to serve as one of Jack's cater-waiters, until he learns that he'll be catering for American Bar Association. Grace discovers Karen's darkest secret: she once made a porn video.

29. Homo for the Holidays

Will and Grace are shocked to learn that Jack never told his mother he was gay and encourage him to open up to her at Thanksgiving. The evening brings a revelation for Jack as well: his father isn't who he thinks it is.

30. Terms of Employment

Grace hires Will to help her sue a deadbeat client, who they learn is actually a ruthless lawyer. Meanwhile Jack and Karen attempt to make a sexual harassment video.

31. I Never Promised You an Olive Garden

Will and Grace ditch their longtime (but boring) friends for a fun loving couple. Meanwhile Jack faces old demons when he accompanies Karen to her stepkids' school.

32. Tea and a Total Lack of Sympathy

In order to get a major client (and thus keep his job), Will must kiss up to Karen like you wouldn't believe; Jack and Grace scheme to appear on Antiques Roadshow.

33. Seeds of Discontent

Grace is excited to meet Will's best friend from high school until she learns that the woman has made a request: to be implanted with Will's sperm.

34. He's Come Undone

Erotic dreams about Grace send Will to a therapist, who seems more interested in Grace. Meanwhile Jack and Karen clash over her treatment of Rosario.

35. Oh Dad, Poor Dad, He's Kept Me in the Closet and I'm So Sad

Will is angry and confused when he learns that his dad has told all his collegues that Will is married to Grace, so as not to acknowledge his homosexuality; Karen thinks she's located Jack's father.

36. Acting Out

Will and Jack appear on Today to protest NBC for cutting a gay kiss out of a egearly-waited sitcome episode. Will is frustrated with Jack on how much he wanted to see that kiss and kisses him. Else where Grace confides in Karen about dumping her boyfriend.

37. Advise and Resent

When Will goes on a blind date arranged by Ben, he is shocked to discover that he is a lousy first date. Meanwhile, Grace continues to stuggle with her wimpish boyfriend Josh.

38. Hey La, Hey La, My Ex-Boyfriend's Back

Will thinks that he has another chance with Michael, his old boyfriend and Grace's new client. Meanwhile Karen decides to take her "career" more seriously.

39. The Hospital Show

After Stan is put in the hospital, Will, Grace, Jack, and Rosario take bets on who Karen will turn to for emotional support. Once Karen finds out Stan is okay, she also discovers the bet going on between her friends. She then makes each one of them do something they would rather not do in order to pay them back, and once they have done what they are asked, she tells them the truth and reminds them that Karen Walker does not do emotions. Afterwards, she goes back into the room where the doctor gives her an envelope with Stan's information. She begins looking through these and starts to break down in tears. Grace walks in to apologize, but once she realizes Karen is crying, she goes to walk back out...yet Karen asks her to stay. Grace helps Karen and afterwards, she gets a little hug from her...then Karen sends her out with a comment on her wardrobe

40. Sweet & Sour Charity

After winning concert tickets from a radio contest, Grace vows to get more involved and she volunteers herself and Will to help out at the community center. Unfortunately, her charitable work conficts with the concert. Meanwhile, while collecting clothes to give to the mission, Jack donates a pair of Karen's most-prized shoes.

41. An Affair to Forget

When their friends Rob and Ellen get engaged, Grace tells Will a dark secret: she once slept with Rob.

42. Girls, Interrupted

Despite their history, Grace spends a fun evening with Val [ from ep. # 18 Grace, Replaced] only to have Will suspect her of stealing. Meanwhile Jack becomes attracted to the leader of Welcome Home-an organization for gays who have converted to going straight, so he acts straight to woo the man.

43. There but for the Grace of Grace

Will and Grace visit their old college professor, whose relationship with his best friend, Sharon, eerily matches Will and Grace's, much to their horror. Meanwhile Jack has a little competition going on with Ben.

44. My Best Friend's Tush

Will helps Jack promote his "subway tush" but is put off by Jack's presentation style; Grace competes with an internationally known interior decorator for a job.

45. Ben? Her? (1)

To help make peace between Grace and Ben, Will has them both over to dinner, only to have their relationship go beyond friendship. But then Will finds out that Ben is dating someone else. Meanwhile Jack catches Rosario in a clinch with a lover and learns that she wants a divorce.

46. Ben? Her? (2)

Forced by his boss to betray both of his friends, Will quits--only to discover that everything isn't as it seems. Frustrated, he leaves a lost Jack and Grace behind and ends up on a tropical island without a care in the world. Until Ben shows up.