My Summer with Amanda (2008)

Aspiring filmmaker Gaby falls desperately in love with supermodel Amanda. But he is too shy and innocent for his sassy, superficial crush — and she is also completely unaware of his feelings. Gaby and his friends decide to hit his uncle's summer house for the season, and everyone in Gaby's crew gives him the absolute worst romantic advice — but he asks for their help anyway. What could possibly go wrong?