There's Something About Mary 1998

A man gets a chance to meet up with his dream girl from high school, even though his date with her back then was a complete disaster.

When a lovesick guy discovers his high school crush is single, he sees a golden opportunity for redemption—until his bumbling attempts to win her back spiral into absolute chaos. As he navigates a minefield of misunderstandings and romantic rivals, he learns that sometimes the path to true love requires embracing your most embarrassing, ridiculous self.