You’re a high school student whose greatest secret—five heartfelt letters written to your past crushes—is exposed when your younger sister mails them. To avoid an awkward situation with your neighbor and one-time crush, Josh Sanderson, you pretends to date the most popular boy in school, Peter Kavinsky, a recipient of one of the letters. What starts as a fake, contractual relationship quickly turns real as you and Peter unexpectedly fall for each other.