History Characters / HalfUponATime

* SkunkStripe: [[InvertedTrope Inverted.]] She has blond hair with a blue streak.

* {{Adorkable}}: He has his moments, especially when he's around May.

* {{Adorkable}}: She has her moments.

* MeaningfulName: Jack the ''[[ThirteenIsUnlucky Thirteenth]]'' often ends up being the butt of everyone's jokes.

* BigNo: [[spoiler: When Jack is about to kill Phillip. And when Jack slices his sword through her chains, because she thinks Jack killed Phillip.]]

* LoserProtagonist: He's basically the ''epitome'' of this--he's the worst in his class when it comes to being a hero, 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. 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).

* DudeWheresMyRespect: Despite being the hero, everyone expects him to [[EpicFail fail]] all the time, and in spectacular fashion.

* FailureHero: He's the worst when it comes to being a hero, as 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 May from putting him down at times. As he says

* LoserProtagonist: He's basically the ''epitome'' of this--he's the worst in his class when it comes to being a hero, 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. 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.

* AwLookTheyReallyDoLoveEachOther: [[spoiler: For all the crap he has with 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.]]

* DeadpanSnarker: Often makes sarcastic and bitter comments and generally expects the worst to happen.

* FailureHero: He's the worst when it comes to rescuing princesses, as 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 May from expecting him to pull epic fails all the time.

* TheHero: 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 adventure.

* EstablishingCharacterMoment: His first scene is him failing the class's princess rescue test.

* EstablishingCharacterMoment: The adventure starts with him failing a princess rescue test in spectacular fashion.

* ButtMonkey: One way or another, the world keeps finding hilarious ways to beat up on him.

* MeaningfulName: Jack the ''[[ThirteenIsUnlucky Thirteenth]]'' can't seem to get a break in his life.

* BelligerentSexualTension: With May. Oh boy.

* FishOutOfWater[=/=]FishOutOfTemporalWater: [[spoiler: When he lands in the real 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, mostly the Jack tales, his reaction is one of stunned shock.]]

* JerkWithAHeartOfGold: As snarky as he is, when push comes to shove, he'll always stick up for his friends, no matter what. To the point where he'll die for them.

* LoserProtagonist: He's basically the ''epitome'' of this--he's the worst in his class when it comes to being a hero,

* GuileHero: 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''. [[spoiler: He manages to outsmart ''[[BigBad the Wicked Queen]]'', of all people.]]
* TheHero: While May and Phillip play 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 adventure.
* HeroicSacrifice: [[spoiler: Pulls this off ''twice''. 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 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.]]

* InsecureLoveInterest: 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. [[TearJerker Frustrated because he thought that he had stopped dreaming about her, he tries to force her out and mockingly tells her that she'll have plenty to say to her prince.]]

* LoserProtagonist: Everyone he comes across thinks he's a loser.

* ReallyRoyaltyReveal: [[spoiler: Turns out he and Jill are the Charmed One's nephew and niece, making them the prince and princess of the kingdom of Charm. In other words, he's Prince Charming. Does that ring a bell?]]
* SavvyGuyEnergeticGirl: The calm and rational Savvy Guy to May's snarky, hot-blooded Energetic Girl.

* TookALevelInBadass: He takes several as the adventure progresses. But the crowning moment is his TrainingMontage, when the Charmed One turns him into the ultimate Eye.

* BelligerentSexualTension: With Jack. A lot.

* DefrostingIceQueen: She initially acts snarky and fiery toward Jack, but warms up to him through the course of the book.
* FireForgedFriends: With Jack and Phillip. Nothing forges a friendship better than surviving life-and-death scenarios after another.