Beautiful Loser (2008)

His parents named him Reginald Regineld. His friends call him "Ditto." At the age of eleven he decided he wasn't going to do anything with his life. And that was going pretty well until senior year when he saw Tracy. This wasn't so much love at first sight as much as it was "completely-head-over-heels-gonna-get-her-at-any-price-even-if-I-make-a-complete-fool-of-myself" love at first sight. And it would burn for decades. Whether she loved him or not.