Ask Again, Yes tells the story of two intertwining families who share a decades-long bond through their patriarchal careers, their being neighbors, their tragedies and a marriage. From their upbringings to their personalities to the events of their personal lives, the Gleesons and Stanhopes are forever tied to each other yet forever in contention given their differences and the events that unfold. Can they move on from where they’ve been? Can their children break the mold of the past? Will their children even understand their pasts as adults?