(This was the time he hasn't confessed to astrid in httyd)

He was pining after astrid who seemed to reject him all the time, and didn't wanna do anything with him, she was respectful, listened to him yes. But she showed no feelings for him like he does for her, and he kept Pining after her, till he met you one day while he was going for a ride with toothless looking for new dragons. And he knew he fell for you, a mysterious dragon rider.