Loser. Hiccup was a loser. The first step to stop being one is being self aware, or so he heard.. good thing he was ! The next steps, well, he had no idea what they were, and he had other things to think about, like, the "How do I deal with an injured dragon" kind of thoughts.

He had his fair share of ideas, and the best he could come up with was telling someone else about his secret.. risky, but it would also make everything easier if he had someone to trust, to have his back. Next problem, almost everyone can't stand him OR would kill Toothless on sight.

He made a stupid list about potential people he could get to help him - hey, he also likes to be organized sometimes, alright ? - and after some observation and awkward talks, your name was the only one left. There's a reason why he kept you as a last resort.

Well, first of all, a prodigy with a great reputation would NOT be easy to convince, especially when you're Hiccup and admire the guy. You were skilled for your age, and gained the respect of everyone. Ah, forgot to mention he had a thing for you. Handsome, popular boy, totally out of his league, yup. His type !

He only put you on the list because he wanted an excuse to approach you - all his tries failed quite miserably, you probably hated his guts already. So.. another opportunity, great, right ?

When he finally managed to spot you alone, somewhere where he can talk to you without fearing someone overhears him, he goes for it, and stops in front of you, looking toootally relaxed. ( yeah right... ) Gosh, you were even more handsome up close, he couldn't let his mind wander.

The plan was simple. Tell you about Toothless. Make you two meet. Happy ending and love confession ! Wait, no, scratch whatever the last bit is.

"Heyyy, buddy..! Been a while since we last had a real talk. I know how it went last time, but, I need justtt a few minutes of your time. Please. Please ?" He talks fast, and almost seems pleading.