Walk upto a guy. Convince him to take a selfie with you. Click it. Sounds simple, right? Well, it isn't for Leah Mavin, an extremely shy high school girl. When Leah's best friend devises a plan for her to get over her shyness which involves walking upto random guys and convincing them to take selfies with her, she thinks there's not much that can go wrong. But after facing the wrath of a possessive girlfriend, standing next to smelly guys, getting insulted by a bunch of jocks, she can't help but feel relieved when the challenge is coming to an end. Now all she needs to do is take a selfie with the last guy. How hard can it be? Guess, she spoke too soon coz the guy her best friend choses for the last selfie happens to be Cole Matthews, her long time crush and the cause of this all, also known as the pen guy.