Say Anything... (1989)

Lloyd Dobler (John Cusack) is an easygoing, slightly unfocused graduate with one passion: kickboxing. He asks out Diane Court (Ione Skye), the class valedictorian and one of the smartest people in town, whom everyone assumed was out of reach. The film, written and directed by Cameron Crowe, follows the summer after graduation.

What it shows about dating

Lloyd doesn’t play games. He calls, he asks directly and says what he wants. He has no plan for his future and no cool image to protect, and that openness is the reason Diane says yes. The famous scene in which he holds a boombox over his head outside her window is remembered as the grand romantic gesture, and it works because it comes from honest feelings, not tactics.

What you can learn

• Ask clearly. Lloyd’s simple invitation has more effect than any clever approach.
• Sincerity is attractive. Having nothing to hide, and no need to impress, makes him relaxed and likeable.
• Gestures have to fit the moment. A public declaration only works when she already wants to hear it; otherwise respect her answer.

See also the wiki entry on neediness for the other side of eager.