Whatever It Takes (2000)

Overview

Ryan Woodman, an awkward high schooler, is infatuated with the stunning Ashley Grant, who seems oblivious to his affections. Conversely, the charming but dim-witted star athlete, Chris Campbell, is drawn to Ryan's intelligent and lovely friend, Maggie Carter. To win over their crushes, the two boys team up, offering each other support in their romantic endeavors. However, as they navigate the complexities of young love, both begin to question if they're truly chasing the right girls, leading to a comedic exploration of teen relationships and self-discovery.