How far would you go to win over the woman you love? The picturesque village of East Upbury still looks much as it did a century ago, but middle-class professionals have long since replaced the agricultural workers who once lived there. When the villagers decide to stage an open-air summer production to commemorate the centenary of the tragic events that occurred there during the Great War, rivalries quickly emerge. The director intends her production to be authentic, but her vision conflicts with the nostalgic view of the past held by influential village factions. Toby has never harboured any desire to appear on stage but has always been fascinated by the history of the Great War. He supports all the director's plans and is delighted to be appointed as stage manager. However, he finds it difficult to focus on his responsibilities because of his fascination with Sarah, a visitor to the village who is helping him backstage. Sarah appears to like him, but the demands of the production mean that whenever they secure any time together events conspire to interrupt them. As the last night of the production approaches, disaster strikes when one of the actors disappears. This forces Toby to confront his fears and decide exactly how far he is willing to go to win over Sarah before she returns to London. By turns tragic, comic, historic, and pastoral, The Woman in the Wings shows that a tragic history can sometimes repeat itself as romantic comedy.