Before the First Curse
Before the casting of the Dark Curse, Killian Jones and his brother Liam are sent to Neverland by their king who secretly are looking for the Dreamshade to take down his enemies. The brothers come across Peter Pan who tells them that Dreamshade is a dangerous weapon and while Killian believes Pan, Liam does not. Trying to prove Killian wrong, Liam injects himself with the Dreamshade, which starts to kill him. Pan helps Killian save his brother by giving him special healing water, which will heal Liam but it means he will never be able to leave Neverland. Although Killian gives Liam the water, they leave the island despite Pan's warnings and Liam dies as they leave Neverland.
Years later, Captain Hook procures a dangerous poison called dreamshade from the thorns of a plant on the island of Neverland and returns to the Enchanted Forest to find the location of a dagger to kill his nemesis, the Dark One. Instead, he is offered protection by Cora to wait out twenty-eight years after the Evil Queen casts the curse over the Enchanted Forest and get even with the Dark One.
After the First Curse
After the breaking of the Dark Curse, Hook teamed up with Cora in finding a pathway to Storybrooke. They both have someone to seek out in Storybrooke, and for Hook, he looks for vengeance against Rumplestiltskin for, many years ago, killing the love of his life, Milah. Once there, his attempts to thwart Rumplestiltskin's new identity, Mr. Gold, are sidetracked when Hook sustains injuries when a stranger's car plows through into town. Later, while Mr. Gold leaves Storybrooke for New York, Hook works together with Cora and Regina to find the whereabouts of the Dark One's Dagger. However, when betrayed by them, he steals back his hook from David, sails on an invisible Jolly Roger and tracks Mr. Gold down to a Manhattan apartment complex. Having previously coated his hook with dreamshade, Hook stabs him in the chest with it, and goes in for the killing blow when he is knocked out by Emma.
On the verge of death, Mr. Gold is ushered back to Storybrooke where he sways Mary Margaret, who has bad blood with Cora, to use an enchanted candle to kill her so he may live. As Cora dies, Mr. Gold is restored to health.
After Henry David, Emma, Hook, Mary Margaret, Mr. Gold and Regina travel through a portal to Neverland in search of him. While combing through the jungle, David leads the group by slicing away stray branches in the way of the path. Blocked by a bushful of thorns, he prepares to cut them down, but Hook hastily stops him. Even though David assures him he can handle it, the pirate refuses to relent and explains the poison oozing from the thorns are the real problem. Additionally, Hook points out it's the same substance he used in a concentrated dose in killing Mr. Gold, and in dreamshade's natural form, it causes inevitable death on an even more excruciating slow level.
Emma, approached by Pan, is given a way to reach Henry in a form of a map. However, she must stop denying her true self, and only then will the map open up for her. After several attempts end in failure, Regina is tired of being toyed by Pan and casts a locator spell on the map, which leads them straight into a pit in the Dark Jungle. At first glance, in the distance, they see what appears to be Henry standing with his back facing them. When Emma calls out to him, the boy is revealed to be Pan dressed in Henry's clothes. Disappointed they tried to cheat at his game, Pan sends the Lost Boys into battle against Emma and the rest of her group. Hook warns to be careful of the Lost Boys' arrows as they are coated with dreamshade. Unfortunately, David is grazed by one of them, and after the fight is over, he brushes it off as a minor injury. In truth, the poison of the dreamshade is beginning to spread rapidly on his body.
Though Emma is able to unlock the map, Pan keeps moving his camp frequently; making it difficult for them to keep backtracking in directions. As a possible solution, Hook suggests they seek the help of Tinker Bell. Noticing Regina is lagging behind in the journey, Emma stops to ask about her relationship to Tinker Bell. Regina refuses to elaborate, and only states it's a "complicated history". Urging Emma to catch up with the others, Regina stays behind to rest. Once alone, Regina, aware she is being watched, calls out a spying Tinker Bell. Hostile and guarded, Tinker Bell knocks Regina out with a whiff of poppy dust and kidnaps her to a cave.
Regina awakens with her wrists bound together with rope, but frees herself effortlessly with magic. However, she underestimates what else Tinker Bell has planned, and soon finds a sharp blade smeared with dreamshade pressed against her neck. Tinker Bell threatens to make her suffer with it, but Regina promises to make things easier, and pulls out her own heart. Placing it in Tinker Bell's hands, Regina asks her to crush it, but a heated exchange follows in which misunderstandings of their past are cleared up. Tinker Bell is convinced by Regina that it's not too late for herself to choose hope over vengeance, and returns the heart unscathed.
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