Say Anything (1989)

Average student and eternal optimist Lloyd Dobler seeks to capture the heart of Diane Court, a beautiful but unattainable valedictorian classmate. He surprises just about everyone - including himself - when she returns the sentiment. However, Diane's divorced, over-protective father soon begins to disapprove of the match, and Lloyd realises that it's going to take more than just the power of love to conquer all.