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Characters / Half Upon a Time

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Watch out! Spoilers abound.


The hero of the story, a 14-year old ordinary boy from the village of Giant's Hand. He lives with his grandfather and is at the bottom of his class when it comes to princess rescues.

  • Adorkable: He has his moments, especially when he's around May.
  • Aw, Look! They Really Do Love Each Other: For all the resentment he has toward his father and Jill, he still can't help but give them a hug when all the fighting is over and everyone is celebrating the victory over the Wicked Queen.
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  • Because You Were Nice to Me: Implied towards Mary. In the second book, when Lian calls him out for sacrificing himself for the others, he responds that she was the one person who didn't treat him like dirt because of his father.
  • Belligerent Sexual Tension: With May, oh so much.
  • Butt-Monkey: He just can't seem to catch a break, can he?
  • Deadpan Snarker: He's as snarky and witty as they come.
  • Disney Death: He actually dies by his own sword at the Queen's hand, but comes back to life because he put a healing potion on his sword.
  • Dude, Where's My Respect?: Despite being the hero, just about everyone he meets tends to have little faith in him.
  • Dying Declaration of Love: In the third book, as he's about to die and he looks at May. He doesn't say anything, but does he really need to? Subverted when he survives.
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  • Establishing Character Moment: His first scene is him failing the class's princess rescue test. Everyone else passed it.
  • Failure Hero: He's the worst when it comes to being a hero, and he's the only one in his class to actually fail the princess rescue test. He starts to grow into a true hero as the adventure goes on, although that doesn't stop the other characters from putting him down at times.
  • Fish out of Water/Fish out of Temporal Water: When he lands in our world six months in the past, he is confused by everything that goes on around him, and it's only by some quick thinking and luck that he's able to get around. When he goes into the library and reads about the fairy tales that inhabit his world (especially the ones about his family), his reaction is one of stunned shock.
  • Guile Hero: His greatest power. He makes mistakes most of the time, but when he puts his smarts and cunning to the test, he can pull off miracles. He manages to outsmart and beat the Wicked Queen, of all people.
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  • The Hero: While May and Phillip play almost as major a part in the story as he does, he is the one who sets off with May to rescue Snow White, and he gets many of the central moments of the books.
  • Heroic Sacrifice: Pulls this off twice. For the first one, when Lian and an army of mermen are chasing after the trio and their mermaid companion Meghan, he lets go of the mermaid and takes on Lian to give the group a chance to escape. And for the second one, as he's about to kill Phillip in the Wicked Queen's throne room, he instead cuts out May's chains and triggers a fight in which the Queen kills him with his own sword.
  • History Repeats: His story draws parallels to the Charmed One's, and the Charmed One straight up tells him that he is destined to walk his path. Well, the Charmed One fell in love with a princess, betrayed the Wicked Queen, and ended up dying by his own sword at the Queen's hands. Guess what happens to Jack?
    • Exploited by the Wicked Queen, who tasks him with stealing a harp from the same giant his father stole from.
  • Idiot Hero: At his worst.
  • Insecure Love Interest: Implied throughout the second and third books, but some moments stand out. When Merriweather tells him about the glass slipper and May's true love, a prince, Jack thinks she loves someone else and Merriweather mocks him for thinking that May would care about him. It's also implied when May appears inside Jack's dream. When that happens, he gets angry and tries to force her out and mockingly tells her that she'll have plenty to say to her prince.
  • Jerk with a Heart of Gold: When push comes to shove, he'll always stick up for his friends, no matter what.
  • Kid Hero: He's just 14 years old and still gets it done.
  • Lightning Bruiser: As an Eye in the third book, he's a good swordsman who can beat up gangs of goblins in little time.
  • Loser Protagonist: He's basically the epitome of this—he's the worst at school, the son of a thief who stole from a giant who rampaged and destroyed everything to kill him, and all his peers look down on him and consider him a loser, especially the town bully, Robert. And he has to save Snow White with nothing but a bag of items, a magic sword, and two friends who can't stand him (at first).
  • Long Last Look: Twice, and both times when he pulls off a Heroic Sacrifice, and he looks at May. Subverted both times when he survives.
  • Meaningful Name: Jack the Thirteenth.
  • Official Couple: With May.
  • Really Royalty Reveal: Turns out he and Jill are the Charmed One's nephew and niece, making them the prince and princess of the kingdom of Charm.
  • Savvy Guy, Energetic Girl: The calm and rational Savvy Guy to May's hot-blooded Energetic Girl.
  • Sins of Our Fathers: Ever since his father stole from the giant in the clouds, he became hated by everyone for this. Jack gets hit with the brunt of it, though, as most of his fellow classmates look down on him and generally don't regard him in high spirits.
  • Took a Level in Badass: He takes several as the story progresses, as he learns to trick and trap his opponents, and becomes a better swordsman able to hold his own against armies of goblins. But the crowning moment is his Training Montage, when the Charmed One turns him into the ultimate Eye.
  • Undying Loyalty: To his friends.
  • Uptown Boy: Meets and falls in love with May (a princess). It's actually an inversion of the original Cinderella story, as May, who is Cinderella and related to the Wicked Queen, grew up as an average girl in our world (which, as Jack notes, puts her as royalty compared to him), and Jack, who grew up an average peasant with his grandfather, is supposed to be the royal boy, since he's the prince of Charm.
  • Vitriolic Best Buds: With Phillip.
  • Well, Excuse Me, Princess!: Has this dynamic with May.
  • Working-Class Hero: He's an average boy who lives with his grandfather in a small village, and who eventually beats the Wicked Queen.


A 14-year old girl who lives with her grandmother in the real world, her grandmother gets kidnapped by a guy in green and his minions, and she falls out of a blue fire portal and lands in Jack's world, in Giant's Hand.

  • Adorkable: She has her moments.
  • Action Girl: Grows into this throughout the story.
  • Belligerent Sexual Tension: With Jack.
  • Big "NO!": When Jack is about to kill Phillip. And when Jack slices his sword through her chains.
  • Break the Cutie: Sorry, May, but your Grandmother is the Wicked Queen.
  • Deadpan Snarker: A classic one. She doesn't go an hour without having something snarky or witty to say. This is exploited by the prison imp, who takes her sarcasm in exchange for Jack reappearing inside the cell.
  • Defrosting Ice Queen: She initially acts like a jerk toward Jack, but warms up to him through the course of the book.
  • Fire-Forged Friends: With Jack and Phillip. Nothing forges a friendship better than surviving life-and-death scenarios one after another.
  • Fish out of Water: At first, when she lands in Giant's Hand, she feels out of place in the world of fairy-tales, but she becomes used to it after a while.
  • Hair of Gold, Heart of Gold: Has blond hair, and is a generally sweet person.
  • Little Miss Snarker: She brings a whole new meaning to the word "sassy".
  • Official Couple: With Jack.
  • Royals Who Actually Do Something: She takes it upon herself to track down all the former rulers of the kingdoms the Wicked Queen conquered after the latter's death.
  • Rebellious Princess: She's a sassy, smart-talking princess who won't sit around and wait for life to get better. After all, she was brought up in the real world, so she would know.
  • Savvy Guy, Energetic Girl: The snarky, hot-blooded Energetic Girl to Jack's calm and rational Savvy Guy.
  • Skunk Stripe: Inverted. She has blond hair with a blue streak.
  • Tomboy Princess: She fits all the check marks.
  • Tsundere: Acts as a type B. The one person she rags on is Jack.
  • Uptown Girl: Meets and falls in love with Jack (a peasant boy). It's actually an inversion of the original Cinderella story, as May, who is Cinderella and related to the Wicked Queen, grew up as an average girl in our world (which, as Jack notes, puts her as royalty compared to him), and Jack, who grew up an average peasant with his grandfather, is supposed to be the royal boy, since he's the prince of Charm.
  • Violently Protective Girlfriend: Attacks the Wicked Queen when the latter tries to go after Jack.
  • Well, Excuse Me, Princess!: Has this dynamic with Jack. She thinks he's a loser and expects him to get everyone killed with his plans.

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