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 gives local newscaster McCoy Whitman a second chance and, with the help of Jack, finally gets to know the man behind the newsman. Grace's campaign for Design Guild President hits a snag when the deciding vote comes down to her old nemesis, Val. Karen acts as Grace's campaign manager, and attempts to secure Val's vote by any means necessary.

When both of their boyfriends ask to move in, Will and Grace use each other as an excuse to get out of it. A snowstorm traps Karen at the office and Jack in an elevator, where he reunites with old flame Drew and tests his commitment to monogamy.

Jack and Estefan's wedding takes a detour when they're forced to get married at the airport by their friend Miss Coco. Will's worried his relationship may turn long-distance. Grace meets a charming guy. Karen reconsiders her commitment to Nikki.

Grace returns from her European travels a new woman, but her elation is short-lived when she receives life-changing news. Karen teaches Will how to be better at phone sex. Jack has a yard sale to discreetly get rid of Estefan's annoying cuckoo clock.

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.