When Karen's has trouble dealing with a personal tragedy, Will, Grace, and Jack try to intervene. Will and Grace's new business relationship begins to show signs of stress.

In order to land a handsome, gay TV news anchor with a pension for dim, frothy men, Jack convinces Will to not be himself and to act like someone silly and stupid. 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. Olympian Adam Rippon has a cameo as a barista with an attitude.

Will is determined to not reminisce about his life in the city or his ex. Grace has false alarms of going into labor. Karen attempts to get closure with her ex-husband. Jack's dream of taking a bow on a Broadway stage becomes a very real possibility.