When Gayngst is the central theme of the story, such a thing is expected.
- When Jack witnesses Astrid kissing Hiccup, he has an intense emotional breakdown. It is there that he realized that he had feelings for the viking. Mavis manages to find him and gets him to confess this, later telling Flynn and Merida too.
- Hiccup confides in Jack and eventually the rest of his friends over the tortures he suffered under Thomas, Peter and Andrew, each time nearly reducing him and the rest to tears.
- Chapter 23. It's filled with death and violence. So long beloved franchise characters. Especially you Ruffnut and Tuffnut.
- Any time loved ones get separated by death. Particularly painful are the two dragon and rider separations detailed.