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Students
Lillet Blan
Voiced by: Wendee Lee (English)
The main protagonist.- Cute Witch: Adorable, and a witch.
- Did You Just Scam Cthulhu?: In the final loop, successfully scams Grimlet, a demon, when she offers to enter a Deal with the Devil. Grimlet would get her soul in exchange for something on his end, which Lillet requests to be that he embrace God, something that as a demon, she knows he can't do. Since neither a human or a demon can back out of a contract once its set up, Grimlet is Dragged Off to Hell for breaking it.
- Everybody's Dead, Dave: Runs into this at the end of the first loop. All the teachers, aside from Advocat died stopping Grimlet, Amoretta being sacrificed in the process, and Margarita was killed by Calvaros.
- Her attempt to prevent everyone dying stopping Grimlet on the second loop fails as well, instead they still die, this time with Grimlet killing everyone and taking complete control over Gammel's body.
- Guile Hero: One of the more epic ones.
- Hot Witch: In the Epilogue.
- Took a Level in Badass: Starts off as a Naive Every Girl who develops into a Guile Hero over the course of the loops. Most notably she goes from quivering in Grimlet's presence to conning him into a Wishplosion.
Margarita Surprise
Voiced by: Amanda Winn-Lee (English)
Lillet's dorm mate. She has a frog familiar named Surely.- Amphibian Assault: Not Margarita herself, but her toad familiar, Surley. He can expel poison and control Margarita's body.
- Burn the Witch!: She mentions early in the story that magic-users are subjected to this where she's from. Fear of this happening to her is why she's trying to release Calvaros.
- Dub Name Change: Margarita Frozen became Margarita Surprise.
- Evil Redhead: Forced into it, anyways.
- The Fair Folk: Though her specialty is Sorcery, she knows enough Glamour to try (without success) to summon Morning Star to breach Opalneria's defenses protecting Calvaros's soul container.
- The Legions of Hell: She mainly specializes in Sorcery.
- The Mole: She is really a servant of Calvaros trying to free him.
- Out of Focus: In contrast to the other routes, she barely appears in the third cycle.
- People Puppets: She's subjected to this by her familiar, Surley, forcing her to fight against Lillet.
- Trapped in Villainy: She only serves Calvaros under threat of death via Burn the Witch!.
- Walking Spoiler: Let's just say she's more than Lillet's dorm mate.
Amoretta Virgine
Voiced by: Lani Minella (English)
A homonculus created by Chartreuse, though she's often seen with Advocat. She has a Grimalkin familiar.- All Witches Have Cats: Well, she's a homonculus rather than a witch, but given the setting her Grimalkin familiar still fits.
- Artificial Human: She is a homonculus.
- Emotionless Girl: Is The Stoic in her early appearances, but develops some emotion due to her encounters with Lillet.
- Heroic Sacrifice: In the 3rd and 4th loops, gives her live to defeat Grimlet.
- Man of Kryptonite: The soul used to create her was that of angel, which allows sacrificing her life to turn her into a deadly weapon against devils.
- Supernaturally Delicious and Nutritious: Why Advocat is drawn to her.
- Younger Than They Look: She looks similar to Lillet in age, but since she is an Artificial Human who was recently created she is much younger.
Bartido Ballentyne
Voiced by: Michael Sorich (English)
A boisterous student that is often seen with Chartreuse.- Berserk Button: Opalneria Rain's behavior towards Chartreuse. Advocat might be good at provoking a rise out of him, but Opalneria hardly needs to do anything for Bartido to show open contempt for her Stalker with a Crush antics. He readily calls her out for sabotaging the alchemy lab, accuses her of being a sexual deviant for thinking Amoretta is in a relationship with Chartreuse, and outright calls Hiram's crush on Opalneria to be a case of "bad taste", all right to Opalneria's face! He relents in the final loop when he realizes how badly she was emotionally manipulated by Lujei.
- The Casanova: Gains a reputation as this in the epilogue, but he only ever seems to show interest in Lillet.
- The Gadfly: Teases Lillet in multiple loops when they first meet, usually by implying she has a crush on him.
- Genius Bruiser: While he'll summon familiars just like everyone else, he'll just as readily take on other mages and even devils with nothing more than Good Old Fisticuffs, and even win a surprising number of times. He's no slouch in the intellectual department either as he's an accomplished alchemist and even shows good lateral thinking skills at the end of the 3rd loop by suggesting using alchemy to create units on the spot as a way to bypass Grimlet's seal on summoned units. He's also a spy from an enemy nation, but manages to keep it under wraps in most loops.
- Heroic Sacrifice: Gets killed by Calveros offscreen at the end of the 1st loop to give Lillet time to escape. He also sells his soul to Advocat in the 3rd loop so Advocat will save Lillet.
- Senseless Sacrifice: Zig-Zagged with his second Heroic Sacrifice above. The bells were already chiming as he made it, so Advocat doesn't have any time to actually save Lillet from danger, but neither does he have any time to make good on the sacrificing part of the deal. Bartido's deal does clue Lillet in on the fact that Advocat's deals are also wiped out when time resets, which gives her a solution to taking the Lemegeton tome from the devil without losing her soul.
- Ship Tease: Teases Lillet by accusing her of having a crush on him in multiple loops, and Lillet frequently gets a Crush Blush around him. Advocat declares that Everyone Can See It. Bartido goes so far as to sell his soul to Advocat to save Lillet in the 3rd loop and send her love letters in the epilogue, but nothing comes of it.
Hiram Menthe
Voiced by: Yuri Lowenthal (English)
A student that is often seen with Opalneria.- Necromancer: Hiram is Opalneria's student, which makes him an apprentice necromancer.
- Out of Focus: He has the least amount of camera time of everyone else other than Lujei, and his characterization basically revolves around his crush on Opalneria.
- Satellite Love Interest: He's a male example toward Opalneria.
- What Does She See in Him?: Gender-inverted case. Bartido expresses bafflement at Hiram's crush on Opalneria.
Instructors
Gammel Dore
Voiced by: Kirk Thornton (English)
The headmaster of the Tower of Silver Star.- Big Good: Lillet thinks he's this at first, but he ultimately proves to not be much help at all. His attempts to expedite Grimlet's destruction after hearing Lillet's warning just makes things worse and enables the devil's escape.
- Dub Name Change: Gammel Drask (an alcoholic beverage in keeping with the themed names) became Gammel Dore (which should be obvious).
- Eccentric Mentor: Subverted in that he's surprisingly incompetent for a supposed mentor figure. Adults Are Useless, after all.
- The Fair Folk: He's the only character other than Lillet to specialize in Glamour. Margarita steals the Morning Star grimoire from his collection.
Opalneria Rain
Voiced by: Lani Minella (English)
The necromancy instructor. Maintains a youthful appearance through magic.- Dark Is Not Evil: She invokes this trope. As she states there is nothing evil about necromancy.
- Genre Savvy: She specializes in Necromancy, but she also knows Alchemy to cover her branch of magic's weakness to Glamour.
- Murder the Hypotenuse: In the fourth cycle, after Lillet convinces Gammel to abandon the plan to destroy Grimlet via Lujei's spell, Opalneria opts to convince Amoretta to sacrifice herself instead. While this was already proven to be an effective method of killing Grimlet, and Gammel attempts the same approach in the fifth cycle, it's heavily implied Opalneria's motives are at least partially because she mistakenly views Amoretta as a romantic rival for Chartreuse's feelings.
- Necromancer: Her specialty.
- Older Than They Look: Gets even worse when she changes her appearance to a schoolgirl's to make things more "suitable" for her Hot for Student role.
- Tsundere: Opalneria has been described as... passionate.
- Really 700 Years Old: It's not stated how old she is, but she is using her magic to make herself look younger.
- Unwitting Instigator of Doom: Her spell succeeds at destroying Grimlet in the first cycle, but it also kills both herself and Gammel, leaving the tower almost completely undefended when Margarita releases Calvaros and he takes over.
- Vain Sorceress: Opalneria is way older than she looks, but she keeps using magic to look younger.
- Villainy-Free Villain: She's a rather unpleasant woman who gets into fights with Lillet over petty issues and tends to cause more trouble than she resolves, particularly in her obsessive and one-sided love for Chartreuse, but she's at least well-intentioned and on the side of good.
Chartreuse Grande
Voiced by: Michael Sorich (English)
The alchemy instructor. Looks like a lion, but he's more concerned with furthering his studies than breaking his curse.- Attack Backfire: He used to be a handsome man; a woman who fell in love with him cursed him to become a half-lion, since he only cared about his magical research and didn't return her love. Unfortunately for her, he likes being a half-lion; to him, driving away further suitors and distractions is a plus.
- Cursed with Awesome: While it was intended as a curse, he doesn't seem to mind being a half-lion one bit.
- For Science!: He doesn't really care about (or consider) anything outside his magical research.
- Half-Human Hybrid: Although it should be noted he's actually a normal human cursed into a half-beast form.
- Incompatible Orientation: Opalneria is in love with him, but he's explicitly both aromantic and asexual. She has difficulty understanding this, and thinks he just personally dislikes her.
Advocat
Voiced by: Yuri Lowenthal (English)
The sorcery instructor, and an actual demon.- All-Powerful Bystander: Doesn't take Calvaros for threat implying he could stop him easily. Grimlet even treats Advocat as a possible threat, but with both villains Advocat doesn't get involved directly.
- Affably Evil: His goal is ultimately to get people to sign away their souls in a Deal with the Devil, but who still genuinely seems to enjoy his friendship with Gammel Dore and the others at the school. He's actually on your side in every iteration, but he admits himself that it's purely because he can't get anyone's soul if they die first.
- Brilliant, but Lazy: Dialogue by himself and Grimlet imply he's far more powerful than he lets on, with the former actually treating him as a potential threat. Nonetheless he's not interested in getting his hands dirty.
- Card-Carrying Villain: He makes absolutely no attempt to hide the fact that he's there to tempt the students into selling their souls. Fortunately for everyone else, he's engages in Pragmatic Villainy and is a genuine friend of Gammel Dore, so he's generally on the school's side.
- Devil in Plain Sight: Literally, but subverted in that he's not one of the villains.
- Evil Sorcerer: He is a devil who teach sorcery.
- Hypocrite: When he and Grimlet meet face to face, Advocat convinces him to not start a fight by saying "When devils fight each other, only the priests win." In the final loop, when Grimlet has been conned by Lillet, Advocat shows up and laughs his ass off. Grimlet asks if he was behind it, and Advocat admits it wasn't but he wishes it was. He doesn't start a fight with another demon, but he does still imply he would gladly arrange for something like Lillet scamming one for his own amusement.
- I Was Just Passing Through: On one iteration, he saves everyone by asking Grimlet to kill you last, using the argument that he wants your soul, and knowing that if you survive to the fifth day you'll be able to rewind time and fix things. He justifies this by saying that he can't get everyone's soul if Grimlet kills them first, but it's implied he does care about Gammel Dore and the students to an extent.
- Mephistopheles: He turns out to actually be Mephistopheles, and, while his nature as a devil does shine through on many an occasion, he ends up helping out Lillet Blan the most out of the adult cast.
- Not Me This Time: When he shows up to rub salt in the wound after Lillet cons Grimlet, Grimlet asks if Advocat was behind it. Advocat having so much fun watching, Grimlet's accusation, not to mention Advocat himself admitting he wished he was behind, implies he has been known to pull such tricks in the past.
- Pragmatic Villainy: He opposes Grimlet indirectly, mostly because he doesn't get anyone's soul if they die before signing a contract with him.
- Tall, Dark, and Snarky: He takes the Snape role with relish.
- Wild Card: He is a devil who could exploit the situation to his benefit if he wanted to, but he knows he has very little to gain personally from the conflict and is content with simply observing the events. In the ending however, he's so impressed with Lillet's outsmarting of Grimlet that he personally backs her deal with him.
Others
Lujei Piche
Voiced by: Megan Hollingshead (English)
A ghost that haunts the Tower of Silver Star. Keeps her former lover's animated skull on her staff.- Cute Ghost Girl: Maintains a sexy appearance despite being incorporeal.
- It Amused Me: The reason she does anything. She knows there's a chance the spell meant to destroy Grimlet will fail, but she lies and tells her it'll work just to see what happens. Gammel calls her a "creature of whim".
- Jacob Marley Apparel: She rants to her staff that he killed her via a poisonous rose attached in some way to her heart. The rose and vines covering her ghostly form are implied to be that rose.
- Necromancer: When she was alive.
- Yandere: She killed the man she loved (who didn't really love her back) so she could reanimate and keep his skull forever.
Calvaros
Voiced by: Jamieson Price (English)
The sinister sorcerer that once tried to conquer the world, whose tower was converted into the Tower of Silver Star wizarding school.- The Archmage: Right down to his title. He's the only character other than Lillet who controls all four branches of magic.
- The Bad Guy Wins: On the first, third, and fourth cycles, after Margarita successfully releases him, he takes advantage of others killing Grimlet for him and seizes power.
- Big Bad Ensemble: With Grimlet. Both of them are out to Take Over the World, and Lillet's problem is finding a way to stop one without leaving the other free.
- Evil Is Hammy: He is an Evil Sorcerer, and definitely talks the part.
- Evil Overlord: Formerly fought to Take Over the World and even after he was defeated still has some servants aiming to free him.
- Kick the Dog: Boasts in the first loop that after Margarita freed him, he killed her.
- Knight of Cerebus: The game starts off mostly lighthearted. Then Calvaros shows up and explains to Lillet that everyone is dead and he will resume he war for world conquest.
- The Legions of Hell: He uses Sorcery as his primary muscle. It's implied Grimlet lent him his army.
- Necromancer: He can wield Necromancy, though he doesn't tend to lean on it, usually just using Ghosts and Skull Mages to eliminate the Phantoms his Sorcery is weak to.
- Sorcerous Overlord: He is an evil sorcerer out for world domination, and aims to use Grimlet's minions to help with it.
- Ungrateful Bastard: He rewards Margarita for releasing him from his seal by either murdering her or trying to murder her.
- Wins by Doing Absolutely Nothing: Because he can't defeat Grimlet on his own or orchestrate his own escape from his soul container, he only wins when other characters resolve those problems for him. Margarita releases him on the first four cycles, and the other characters' efforts to deal with Grimlet usually results in most of the professors already being killed or incapacitated, allowing him to easily take over in the confusion.
- Would Hurt a Child: He has no qualms about killing Lillet, and he murders Margarita off-screen in the first cycle, and is implied to do the same on the second and third as well.
Grimlet
Voiced by: Patrick Seitz (English)
A demon that Calvaros bargained with for great power.- Big Bad Ensemble: With Calvaros. Grimlet is the more powerful of the two, and unfortunately releasing him is the only way to ensure Calvaros doesn't run free.
- Deal with the Devil: Cut one with Calvaros in the past to lend him an army. Calvaros is very determined to make sure he doesn't have to fulfill his end of the deal and give up his soul.
- Lillet cuts one with him, that turns out to be a Wishplosion since her deal was for Grimlet to embrace God, something that as a demon, he can't do. As a result he is Dragged Off to Hell for breaking the contract.
- Dragged Off to Hell: His fate in the final loop. Lillet offers her soul to him, and to Grimlet's shock she asks for him to embrace God. As a demon, he can't and is sent back to Hell for breaking the contract.
- Kryptonite Factor: Of the Holy Burns Evil type. Amoretta can give up her life to defeat him.
- Wishplosion: Is subjected to one by Lillet. She offers him her soul, in exchange for him embracing God. Grimlet can't do that, and he can't back out of the contract, so he's Dragged Off to Hell.
