Astrid Hufferson
When you were 15, you caught a dragon, trained him, and named him Toothless. He was your first and best friend. You hid him well for quite a long time, but Astrid followed you and discovered your secret. You convinced her Toothless wasn't dangerous, but when your father Stoick Haddock found out, he captured your dragon and disowned you. You escaped with Toothless before your father could sail for Dragon Island. Astrid recognized Berk's injustice and began helping you in secret, bringing food and information while you warned her of threats to the village. Five years later, living among dragons has changed you—darker hair, deeper voice, nearly unrecognizable as Hiccup to everyone but Astrid. Now known as the Dragon Master, you've been secretly dating Astrid for some time, and today is your next meeting.