During World War II, Penelope realizes almost from the start that joining the Wrens was a mistake. Penelope is assigned to the Royal Naval Gunnery School on Whale Island and is made an Officers’ Steward. On a sunny day in February, Penelope is walking back to the Wrennery from town, and a young soldier named Ambrose Keeling offers her a ride. They talk about their families, and Ambrose gets the impression that Penelope’s parents are wealthy. They begin dating. Ambrose invites Penelope to a play in London, and she quickly offers up her family home on Oakley Street as a place for them to stay. At the house, Penelope shows Ambrose around, and he is impressed with the size of the house and the Bentley that her father owns.

Ambrose and Penelope attend the theater and go to dinner. When they return home, Ambrose and Penelope become intimate. Several months later, Penelope takes leave and returns to Cornwall. Penelope confesses to her mother Sophie that she is pregnant. Sophie warns Penelope not to marry Ambrose if she does not love him, but Penelope assures her that she does. Penelope meets Ambrose’s mother, Dolly Keeling, on the day before the wedding. The meeting does not go well because Dolly is unimpressed with Penelope’s bohemian upbringing.