Doormen go on strike, transforming the Upper East Side into a war zone. Meanwhile, Jill and Andy have a Valentine's Day dinner, where they pick sides in the strike, and Lex and Brooke take a big step in their relationship.

Age issues plague Jill, Andy and Vanessa. Also, Jill and Andy head to a "Dinner in the Dark" with Lex and Brooke.

Things go from great to gruesome when Jill, Andy, and the kids drive to a party in the Hamptons and get stuck in a traffic jam where Jill has a run-in with Brooke's idol, Joy Green (Molly Ringwald), author of The Joy Manifesto. Lex gets an enticing offer for Brooke's company, but Brooke has other ideas.