Note: Despite the title, the story has NOTHING to do with Taylor Swift. --- When new-girl-in-town Reese is at the mall, her newly purchased lingerie falls out of her shopping bag and an attractive teenage boy picks them up for her after making some inappropriate comments. She hopes that word won't get around, but as luck would have it, he turns out to practically be her neighbor. She begins hanging out with him, and he makes her a bet. To win the bet, she must pretend to be a guy at the start of school (which is quickly approaching) and convince everyone at Blair High of it. The bet is off once someone realizes that she's a girl. So begins the extensive training of Reese on how to act, dress, and talk like a guy, and most awkwardly, on how to pick up girls. Soon after the bet is made, Ashton begins to see Reese as a gorgeous and witty girl rather than someone to fulfill his bet, while Reese struggles with falling for him and remaining loyal to her boyfriend from her old town.