Eighteen-year-old Logan Witherspoon has just discovered that his girlfriend of three years cheated on him but things start to look up when a new student enrolls in his small-town high school. Tall, unconventionally pretty, and a bit awkward. Sage Hendricks appeals to Logan at a time when he trusts no one. And as Logan learns more about Sage, he realises that she needs a friend as much as he does, if not more. One day , he acts on his growing attraction and kisses her. Moments later, he wishes he hadn't. Sage discloses a secret: biologically, she's a boy.
Enraged, frightened, and feeling betrayed, Logan lashes out at Sage. Once his anger has cooled, however, his regrets lead him to attempt to rekindle thier friendship. Impressed that Logan is even trying to understand, Sage agrees to give him a second chance. But LOgan has no idea how rocky the road back to friendship will be, or how many unexpected, exciting, and painful places he and Sage will visit along the way.