Question: If Lucy's father was the one that gave Henry the Beach Boys CD, how could Henry take that as a sign that Lucy remembers him?
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Chosen answer: Lucy's father previously told Henry that she only sings on days that she meets him - then you see a flash of her painting in the garage, singing a Beach Boys song. Right before he hands Henry the Beach Boys CD, he tells him that she's even singing again. Henry realized as he listened to CD - maybe if she is singing again, she is thinking of him, hence, remembering him. (It happens to be the same song that she was singing in the garage that's playing on the boat when Henry turns around to go back. It's called 'Wouldn't It Be Nice').
Why wouldn't the father just tell him directly "hey she's been painting and singing again, so she probably might remember you"