It made no sense that she wouldn't be angry unless there was something more to the way she felt about him- more than just the respect the other villagers had. He'd seen it in her smile and disregarded it simply because he couldn't believe it could be true. No one had looked at him that way since Astrid. 

He called for Toothless with a whistle and as the nightfury passed by under them he smiled at Castiel and then dropped onto the saddle. The black dragon carried him up through gaps in the flock and they circled around to drift close to Castiel. Hiccup extended one hand towards her: "come on." He encouraged, wanting her to climb on board. "Let me really show you Berk." She was fully healed now and he wanted to take her on a true flight. Without all the careful restrictions. Toothless rumbled in agreement because he knew how well a romantic flight had worked out last time- oh he'd let his human show her their aerial skill but once that was over it was fair game.