America Rossi has been thrown into the dark side of teenage life, unprepared. Now she must figure out her senior year goals for The Assignment, a four-year long project of goal setting and letters of reflection. But after years of unexpected heartbreak, traumatizing sexual experiences, and uncovering some harsh societal truths, she's found herself with no goals. In hopes of finding a renewed outlook, she decides to open the Freshman, Sophomore and Junior letters that were already completed for The Assignment. The letters take her back to the start of high school and into the relationships she has desperately tried to forget. Will reading these letters remind her of how far she’s come, or will they send her into an even darker place? She has to take time to look back on where she's been to understand where she wants to go.