Scott Woolley, an old high school classmate seeks revenge on Karen for ruining his senior year by trying to become President of Walker Inc. After Scott prepares a presentation that wows the board of Walker Inc.,he takes over conrol of teh company, much to karen's dismay. Meanwhile, Jack and Grace take the day off of work to go to the movies. While at the supermarket getting snacks, they run into Vince and his co-worker and assume that Vince is cheating on Will.

Scott Woolley, under the alias, Haley Joel Osment, hires Grace to design his new restaurant under the condition Grace fires Karen from her design firm. Grace later tells Karen about the incident and they realize the man that hired Grace is really Scott Woolley. Grace and Karen decide to trap him in his lie. Meanwhile, Jack takes Will out for a boys' night to get his mind off of Vince, but ends up abandoning Will at the club. Will upset over being dumped at the club confronts Jack about his behavior. In an effort to make it up to Will, Jack takes him out to lunch and tries to ignore everyone around him except, Will. The task becomes incredibly difficult once Jack realizes Patti Lupone 9guest star as herself) has entered the restaurant. The waiter at the restaurant request Patti sing, "Don't Cry for Me Argentina". Before she sings she asks the surrounding patrons, including Jack, if it's all right with everyone if she sings. Jack, trying to ignore her request goes off on her. Will impressed by Jack's behavior is touched, thus proving Jack truly does cares for him. As Jack's reward, Will let's him cut a piece of Patti's hair to add to his wig collection.