In order to land a handsome, gay TV news anchor (guest star Matt Bomer) with a pension for dim, frothy men, Jack convinces Will to not be himself and to act like someone silly and stupid—does he know anyone like that? Karen learns that her alimony will be severely limited unless she can get photos of her ex-husband's affair with Lorraine Finster, so she enlists Grace to go with her to the strip club where Lorraine works.

Will and Grace's plan to win over Will's new boss goes awry when he drops dead in their apartment; Estefan and Karen's mutual dislike puts Jack in full damage control mode at his birthday dinner.