While on night patrol, Stoick is ambushed by the Flyers and gravely injured, leaving Hiccup torn between his duties as a son and as the Riders' leader.
- Art Shift: At the start of Astrid's story, it shows stock-footage taken from the movie of the moment Hiccup was aiming for Toothless. It shifts back to the show's cheaper animation shortly after and it is very noticeable.
- Cliffhanger: The episode ends with a gravely injured Heather telling the gang that the Dragon Flyers are attacking Vanaheim.
- Foregone Conclusion: Stoick is believed to have been "fatally wounded" in this episode, but since it takes place before the second movie, we know he's not going to die yet.
- In Spite of a Nail: All of the Riders' versions of what would have happened had they not left Berk for the Edge results in Krogan and Johann attacking Berk. Astrid's meanwhile has Hiccup losing his leg and befriending dragons even if he had never shot down Toothless, since he would have come across Toothless eventually in that cove, and not have been able to kill him, then Astrid posits that the Whispering Death would have attacked, causing Toothless to grab Hiccup and make a run for it.
- Heroic BSoD: Hiccup suffers one after learning about Stoick's injury, believing that it was a culmination of all the choices he made that changed both Berk and dragon-kind, and the series-long journey to the great beyond. Astrid later snaps him out of it.
- King on His Deathbed: Stoick is badly injured by the Flyers on a flight out and is being tended to by Gothi. Because he was more or less the reason the Flyers targeted his father, Hiccup suffers from a crisis on his decision to leave for the great beyond in the first place. Later averted when he gets better by the end of the episode.
- Refusal of the Call: When he is told that he has to step up and be the chief until Stock recovers, Hiccup refuses on the grounds that it was because of his decisions that Stoick was left in the sorry state that he is in.
- Suddenly SHOUTING!: Hearing the riders' interpretations of what would have happened if they stayed on Berk (mostly comedic) does not help Hiccup's mood in the slightest, and their bickering over which scenario would have been more plausible finally makes him snap. Everyone present is noticeably more shocked at this than the time Hiccup suspended Snotlout from the dragon-training academy.
- That Came Out Wrong: When Hiccup tells Toothless he did not regret shooting him down.
- What If?: Each member of the riders tell their own interpretation of what may have happened if Hiccup and the riders decided not to pursue the mysteries of the Dragon Eye and stayed on Berk "Rashomon"-Style.
- Ruffnut and Tuffnut claim that if they did not venture off to what would eventually become Dragon's Edge, the twins would proceed to escalate their pranks more and more around the village and go "full Loki." Not only would it lead to uncontrolled chaos throughout the whole village, it would lead to a fish-throwing civil war before the Dragon Hunters led by Johann and Dagur would invade, all of Berk completely unprepared.
- Fishlegs claims that all of Berk would have been peaceful, civilized and free of all conflict, interpreted as being similar to a flower-power commune, complete with meditation, flower-crowns and frolicking. Peace would have been brokered between Berk, Dagur, Viggo and Johann... before the Dragon Hunters summon their Flyers and destroy everything. Subverted, as Snotlout was the one who interrupted and pointed out that they would have sprung the trap under those circumstances.
- Snotlout claims that if his job as weapon's tester were to continue, he would have been promoted to official weapons inventor. He would have created an over-the-top super weapon - the Mace-Axe-Sword - and be revered by everyone, including Gobber, Astrid, Ruffnut and his father, complete with a statue made in his honor.
- Astrid, on the other hand, has the first movie's premise play out pretty much the same way. The only differences are the setting (this being still on Berk), the condensed timing of events to each other, the Whispering Death's arrival replacing the Red Death's debut (with its rivalry with Toothless still being relevant and present), and the way Toothless and Hiccup lose their limbs: Hiccup gets his leg burned and shot off by one of the Whispering Death's attacks, and Toothless still has his tail fin intact after getting shot down but loses it shielding Hiccup with his tail.