My Greatest Failure: Nine years ago (as of Season 1-2), he and Rook were separated on the day they stayed out too late after he had been late for his appointment. He has been obsessed with keeping his word ever since.
Parental Abandonment: His parents died when he was little and his guardian, Baron Kaido, sent him off to a boarding school in England.
Team Mom/The Heart: Even though she stinks at solving puzzles, she's essential to the group because she helps keep the others at least somewhat grounded in reality, and brings Kaito back from his Heroic BSOD.
Made quite literal when Freecell decides that she is going to be his new 'mother.'
Hypocrite: So he thinks that Kaito has to be dealt with because his armbad makes him disregard the lives of his friends and he constantly puts them in dangerous situations. What is his solution Join POG and try to kill Kaito with his puzzles, therefore putting his friends into even more dangerous situations.
Then there's the fact that Kaito friends have gotten into dangerous situations of their own free will without telling Kaito including Gammon and Gammon only survived the exorcism labryinth puzzle in Venice thanks to the armband.
The Starscream: After joining P.O.G. he tells Elena is is going to crush both Kaito and Rook
Smug Snake: Ever since he became a Giver and before it as well. The first time as a Giver Kaito showed mercy on him while Gammon kept on trying to egg him on into beating him and proving he's right. The second time Kaito chose not to take the two beams and win thanks to the vision he saw though Gammon doesn't know this. The Puzzle involving vehicles and the Exorcism Labryinth puzzles he couldn't solve were solved thanks to the armband. Yet he still acts like he is better than Kaito and the armband in every way.
Out of Focus: In season 3. Cubic only gets one focus episode to himself and even then has to have Kaito come and help him solve that episode's puzzle. The only other episode he has is shared with Ana. He is even passed up as one of the Phi Brian's that Orpheus wants to possess.
Ana: Hey, this is a Lolacchi! Michen-an! Ruben-pi!
Out of Focus: In season 3, even worse than Cubic. Ana has no focus episodes to himself and the closest he gets is one shared with Cubic. He is also passed up for being one of the Phi Brains that Orpheus wants to possess.
Underestimating Badassery: Ana's abilities are frequently underestimated by friends and foes alike, and in the latter case his carefree antics tend to annoy his opponents so much that they don't see the finishing move coming until it's too late.
Unsettling Gender-Reveal: Despite the crossdressing and girlish looks, Ana identifies as a boy which he will immediately tell whoever is mistaking him for a girl. It leads to some very comical facial expressions, such as Maze and later Raetsel.
Broken Pedestal: Kaito learns that his perfect image of Jin isn't as good as it appears in season 3 concerning the one year where he disappeared. Though how broken is something the characters are trying to figure out. Amongst other things he created Fools Puzzles but also solved many of them so they wouldn't harm others, entered some form of contract with Enigma and Raetsel, and has said he hated puzzles.
Averted. It turns out that Enigma twisted Jin's hatred on puzzles from his own after his childhood friend, who was Jin's rival, died due to a Fool's puzzle.
Distressed Dude: The poor guy had been a captive to POG in Season 1 and later, in Season 3, where's he's kidnapped by Raetsel and possessed by Orpheus.
Laser-Guided Amnesia: He has forgotten all of his past and only recalls certain tiny tidbits after regaining his self during Season 3. Before that he barely ate and spent most of his time just playing with puzzles puzzles.
Later in episode 17 of season 3, it turns out that his memories weren't completely lost, only locked away by Orpheus, who possessed his body.
Stalker Without A Crush: He suddenly starts telling what he knows about Kaito during the Rink Slider game, from what happened to Rook nine years ago to how Kaito was out of shampoo when he took a bath the night before. What's funny is that it is Cubic who confirms this.
Irrational Hatred: Towards Ana, to the point where she wonders to herself why she loathes Ana so much. Some of it does seem to come from the fact that her friend Eve's dreams being crushed when she saw how much better her brother Ana was at drawing. The rest most likely comes from the armband influencing her.
Well-Intentioned Extremist: How he views his actions as a member of the Orpheus Order. He joined as he believed the one chosen by the orpheus ring is destined to lead humanity, which would be either Kaito or Freecell after their final battle.
Psycho Prototype: Was the test subject for the first generation of Replica Rings. The Ring warped her emotions so that even though she loved her son, there were times when she felt uncontrollable hatred for him.
Ignored Epiphany: She was starting to doubt whether Jin really hated puzzles, but then goes back to her old ways after Enigma sent a Master Brain who tried to assassinate her and the others. Ana even mentions her scent is gone.
Insane Troll Logic: Clearly it's Kaito's fault that Jin is being hurt by puzzles even though they are the ones sending the Master Brains to assassinate Kaito with the deadly puzzles that cause Jin pain!
Teacher/Student Romance: At least implied on her side when it comes to Jin. The jury's still out on what Jin feels.
Unwitting Pawn: Raetsel doesn't have an idea what Enigma is up it. She only knows that Enigma wants to fulfill Jin's wish to eliminate all puzzles but she's being used by him several times for some underlying motive of his.
Villainous Breakdown: When she learns that Jin doesn't need her, but instead Kaito, she breaks down. Raetsel then convinces Jin to come with her and makes both Enigma and Kaito chase after them.
Freudian Excuse: His fiance, Lovushka, died while solving a Fool's puzzle in order to become a Phi Brain and restore her country's wealth which made him hate puzzles. But it turns out that he led her to her own death by not telling her about the country's rising economy and he blames the puzzles for it.
Hidden Agenda Villain: While he says he's trying to fulfill the contract with Jin, he seems to be up to something else.
Manipulative Bastard: Enigma is very cunning and was not only able to convince Raetsel to continue her mission after sending a Master Brain to kill her and the others, but reset the disarmed puzzle that Melancholy made since he knew she was only faking being his ally and then put her into the puzzle.