Can't Hardly Wait (1998)

This is a movie about the last night of a group of high school graduates are together. Preston Meyers (Ethan Embry) has just learned that the love of his life and recently dumped Amanda Beckett (Jennifer Love Hewitt) will be at the post graduation party that night. He is accompanied by his down on men and the world best friend, Denise Fleming (Laura Ambrose). One guy, Kenny Fisher (Seth Green) is a wanna-be rapper and has vowed to lose his virginity that night. He is hated by Denise. The two find themselves thrown together in a twist of fate and sparks might just fly if they can stand one another long enough. Preston spends the whole night trying to tell Amanda how he feels, hoping to get his true love before he leaves town in the morning.