Sierra accidentally agrees to go out with Charlie, the weirdest boy at school. She's too nice to break up with him, so she and Lily hatch a plan to get Charlie to dump her instead. Their plan backfires however, and Charlie falls deeper in love. Sierra pulls out all the stops and finally gets Charlie to call it off - but her victory is bittersweet because she realizes that she has fallen for him - and needs a new plan to win him back.