Say Anything... (1989)

In a charming, critically acclaimed tale of first love, Lloyd (John Cusack), an eternal optimist, seeks to capture the heart of Diane (Ione Skye), an unattainable high-school beauty and straight-A student. It surprises just about everyone when she returns the sentiment. But Diane's overly possessive, divorced father (John Mahoney) doesn't approve and it will take more than the power of love to conquer all.