American Pie (1999)

Overview
At a high-school party, four friends find that losing their collective virginity isn't as easy as they had thought. But they still believe that they need to do so before college. To motivate themselves, they enter a pact to try to be the first to "score." And of course, the senior prom is their last best chance. As the fateful date draws near, the boys wonder who among them will get lucky.