Trivia: Allen Covert, the actor who played "Ten Second Tom," is an old friend of Adam Sandler's who has been in 13 of Sandler's last 15 films. He was also in three of Drew Barrymore's films.
Trivia: When Henry (Adam Sandler) is at the golf course with Ula and his kids, everyone except Henry is teeing off in the same style as Happy Gilmore (also played by Sandler) in "Happy Gilmore" (1996). When Henry sees this, he replies, "That is the dumbest thing I have ever seen."
Trivia: The original title of this film was "50 First Kisses", but was changed to avoid confusion with Drew Barrymore's vehicle "Never Been Kissed".
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"