America Rossi's life used to be easy. She worried about not missing Saved by the Bell reruns, collecting enough Lisa Frank school supplies, and trying to convince her parents to switch from VHS to DVD. That was, until high school changed it all.

The start of a new millennium was also the start of America's real-world experiences. They were nothing like she thought they'd be. Not her first kiss or the boys she thought she loved. Not the town she grew up in or the peers she thought she knew. 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.

Were things really that bad? In hopes of finding a renewed outlook, she decides to open the freshman, sophomore, and junior letters she 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?