High School student Hiccup is a bad boy, in with the wrong crowd and a pest to those around him. Astrid Hofferson is Class President, cheerleading Captain and most popular girl in school. But neither are what they seem: Astrid's popularity hides a determined but very insecure young woman battling against impossible expectations while Hiccup struggles in an abusive home he endures for the sake of his ailing mother. Both wear masks at school-but can they see behind the other's facade and help each other through? Modern AU, Hiccstrid.