The To Do List (2013)

It's 1993, and high-school valedictorian Brandy Klark (Aubrey Plaza) decides she needs to shed her uptight image before college. She puts together a list of all the activities -- including sex -- she missed in high school. When she soon realizes she is out of her depth, Brandy enlists the aid of her friends, older sister, and boss. Summer marches on, and members of the group realize that they will need plenty of imagination and open mindedness to complete her project before September.