In order to land a handsome, gay TV news anchor (guest star Matt Bomer) with a pension for dim, frothy men, Jack (Sean Hayes) convinces Will (Eric McCormack) to not be himself and to act like someone silly and stupid - does he know anyone like that? Karen (Megan Mullally) learns that her alimony will be severely limited unless she can get photos of her ex-husband's affair with Lorraine Finster (guest star Minnie Driver), so she enlists Grace (Debra Messing) to go with her to the strip club where Lorraine works. Olympian Adam Rippon has a cameo as a barista with an attitude.