Harrison Haddock's life is a mess. His final year at Berk High is nearly over and things are not looking good for him. His father ignores him, his peer's ignores him even Astrid, the girl who Harrison is in love with ignores him. Harrison doesn't know what he's going to do, but that all changes when he bumps into a person who gives him an idea that could turn his whole life around.

Hoping to forget her depression, Astrid Hofferson decides to call a hotline number she finds on a flyer posted on her university campus. Astrid talks with one of their angels, a young man known simply as "Hiccup" which greatly helps. If only she could find this "Hiccup" and talk with him face-to-face. Can't be that hard, right? Not with a voice as unique as his...or so she thinks.

Dragged to a bar by some of his friends to celebrate a promotion, Hiccup Haddock consequently has to play a game of truth of dare, and the dare involves a certain blonde woman.