Will & Grace S10E08 - Anchor Away

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.