Wendy struggles to pick an outfit for her date with James, and she finally settles on a dress that is flattering without being too revealing. She relishes the idea that James might like her for who she is, rather than for who her father is. As she gets ready to leave, she sees her brother, Jon, working on model airplanes. Jon is happy at home, and Wendy feels bad that he will be sent to boarding school soon.

Wendy thinks about canceling her date with James, but she decides to follow through with it on the chance that news of her date will draw her father back home. At the coffee shop, James is early, and he and Wendy flirt again. Angie encourages them to head out, telling Wendy to have fun. In the car, James gets very close to Wendy but backs away long enough to drive the car.

James brings Wendy to the Tiger Lily, the yacht he lives on. The boat is impressive, and the first mate, Smee, has prepared a dinner for them. They eat and chat, but James gets irritated when he suspects that Wendy is giving him a fake smile. She agrees not to display fake emotions, but she then turns the accusation around on James, noting that he is only showing her his possessions rather than allowing her to get to know him as a person.