Grace finds out that Karen once starred in a fetish video, causing Karen to be so embarrassed that she quits her job as Grace's assistant. However, when one of Will's acquaintances starts treating Jack horribly, Will stands up for his friend and rejoins the wait staff. Jack challenges Will to become a cater-waiter on his staff, but when Will finds out that the catered event is for the American Bar Association, he backs out and joins the dinner guests.
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Stan puts Karen on a budget to stop her wild spending, and she becomes terrified when Grace takes her to an outlet mall to teach her how to shop smarter. But Will gets a harsh lesson when Harlin decides to fire him, leaving the lawyer without any prospects. Will's ego inflates after closing a major deal for Harlin, and he decides to focus solely on the millionaire's business by dumping all of the smaller clients who supported him when he first became a lawyer. Luckily, Jack makes a big show of his love for Rosario, and the INS officers passes them just for trying so hard. Jack and Rosario are being interviewed by the INS to make sure their greencard marriage is for real, but it turns out their interviewer is somebody that Jack has met and hooked up with before. Grace finally admits that even though she's been telling her mom to stop setting her up for years now, she feels bad that her mother has actually stopped. Grace looks at this as an opportunity to show her mother how bad she is at setting people up, but is horrified when Will actually gets along with the guy. It turns out, however, that her mom is more interested in setting up Will with someone. Grace's mom comes to town and Grace is scared that her mom will try to set her up again. Will feels terrible, and tries to arrange a reconciliation between Jack and Walter, but when he does so it turns out that Jack was thinking about someone else and he isn't interested in Walter at all. Jack finds out that Will hooked up with his ex-boyfriend Walter and dumps Will as a friend because Walter was the love of his life. He calls her too shallow for his taste and quickly ditches her. With Karen's help she buys a water-filled bra that makes her look much larger up front than she is, but she springs some leaks while on her date at the art gallery and has to admit to her crush that she's wearing a water-bra. When an old high school crush calls her and asks her out, she is incredibly excited until Karen points out that she'll now have to live up her published dimensions. Grace is written up in the newspaper with an accompanying picture that makes her look much bustier than she actually is. And the keys are only to Grace's office anyway. Karen finally gives him the keys to an expensive boat, and he finally feels so guilty that he tells her what he did, and then she tells him that she actually knew all the time because she had video cameras everywhere. When Guapo comes back, Jack hides the bird in the closet so that he can keep getting expensive gifts from Karen. Karen lets Guapo, the parrot out the window by mistake, and goes on a buying spree for Jack to make it up to him. But Grace isn't sure she wants the position when Will actually seems psyched to not have the job anymore, and she starts being pestered by all the tenants. They run an ugly race, slandering each other and buying vote, and in the end Grace wins when the two of them pester the last tenant for his vote while he's in his hospital room. When Grace finds out that Will, acting as tenant board president, is the only tenant with a working fireplace, she decides to run against him in the upcoming election and take him down a notch or two in arrogance.
Jack has to move in with Rosario in Karen's apartment to make things look good for the INS. Will stresses about a date with a man from a bookstore. Grace moves into an apartment across the hall and decides to throw a party without Will's help to show her new-found independence. Note: the episodes on the Season 2 DVD are not in the same order as the broadcast dates shown below. Veronica Cartwright as Judith McFarland.
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