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The Heroine of the game. She's a witch with the power to foresee the future. She has her blood sucked by vampire brothers Rupert and Alfred and forced to be their "belonging". She has ten days until she becomes a vampire.
- All Girls Want Bad Boys: Three of her love interests are vampires and two are werewolves.
- Curtains Match the Window: Subverted. Her hair is black, but the ends are purple like her eyes.
- Dark Is Not Evil: She's a witch, wears black clothing and has black hair. However, she's a nice girl, especially considering that she's stuck in a hotel filled with supernatural beings.
- Dude Magnet: Like any other Dating Sim and the rest of the Shall We Date? series, she has a habit of attracting a lot of male attention.
- Even Girls Want Her: In Jack's route, Bridget attempts to turn her into a belonging. When she fails, Bridget declares that she will make the player her belonging.
- Hello, [Insert Name Here]: Her name is set to default in the beginning. However, the player can change her name whenever they like.
- I Choose to Stay: In the Serenade Ending (and sometimes in the Toccata ending as well), she will abandon her quest to turn back into a human.
- Identical Granddaughter: Implied with her ancestor, Tatiana.
- Purple Eyes: Indicating her witch heritage and her mystical abilities.
- The Seer: She can "see" into the future at random moments in time. The visions always come true and these visions often Foreshadow certain events, especially the climax of the route.
A talking cat who helps Mina in her quest to become human again.
- Meaningful Name: If you look closely, you can see an actual spade on his back.
- Mentor Archetype: He serves as one for Mina.
- Properly Paranoid: He says that Mina should be this, considering the brothers are trying to use her for their own purposes. He will abandon this idea the further the player goes along her selected route.
- Talking Animal: Although it depends on who he talks to and his willingness to cooperate with them.
- Team Pet: He reveals that he's Harold's pet cat.
Alfred's older and more collected brother. He's one of the vampires who took Mina's blood in the prologue. He and Alfred are descendants of Harold, the father of vampires.
- Beware the Nice Ones: At first, he seems like a nice guy. However, he has a dark side that's hinted at multiple times in the game.
- In Jack's route, he tries to attack him with a sword.
- Big Brother Instinct: He tries to show his brother how much he cares for him. However, since his primary concern is trying to make Mina love him and fulfill his grandfather's will, his brotherly affection is put on hold.
- In Chapter 9 of his route, he gives some of his blood to heal Alfred who was injured by Daniel's bullet.
- Bookworm: He likes to spend his time in the castle's library.
- Freudian Excuse: Harold raised him in a strict household. Thanks to him, he never learned what love was and he seeks the destruction of Rosapast. It turns out that Harold did love him, but he had a hard time showing it.
- Green Eyes: They turn red when he tells Mina to do something or when he takes her blood. When his eyes turn red and he orders her to kiss him, he quickly realizes that she's not his belonging.
- Heroic BSoD: He goes into one in his route after Alfred is injured by Daniel.
- I Just Want to Be Free: His wish for his route is this. He wishes to no longer be bound to castle and explore the world. In the Toccata Ending, he allows Mina to turn back into a human and wish for his freedom so that he can visit her any time he wants.
- Knight Templar Big Brother: One the reasons why he tries to destroy Rosapast is because Alfred was injured trying to keep Rosapast out of the werewolves' hands.
- Lethal Chef: Jack tells Mina that Rupert once made sour cookies.
- Subverted in his Maiden Desire route. While he makes unattractive food, it's not as bad. It certainly helps that he made the food for Mina to recover from blood loss.
- Love Redeems: In the Serenade and Toccata Endings, he refuses to kill Mina when she starts defending Rosapast.
- Nice Guy: He's primarily this, but that can change if something upsets him.
- Perpetual Smiler: He's almost always seen smiling. Mina acknowledges that when he refused to let her go that his smile became more unnerving rather than comforting.
- Royal Rapier: His weapon of choice.
- Sibling Yin-Yang: He's calm and gentlemanly while Alfred's angry and forceful.
- The Unfavorite: During his route, he reveals that he felt like this growing up. He felt like Alfred was favored by Harold and Tatiana and wished to be like him. It turns out Alfred felt the same way.
- What Is This Thing You Call "Love"?: He has never been loved before curtsey of his ancestor, Harold. During his route, he tries to explore the aspect of love. Although he initially tries to gain The Heroine's love for his own purposes, he gradually falls in love with her.
- You Gotta Have Blue Hair: With a little bit of green on the ends.
Rupert's younger and more abrasive brother. He was one of the vampires who took Mine's blood in the prologue. He and Rupert are descendants of Harold, the father of vampires.
- Adorkable: He could come across as this, especially when Spade is close-by.
- Curtains Match the Window
- Jerk with a Heart of Gold: Although he comes off as a complete jerk in the beginning, he turns out to be pretty nice deep down.
- His primary goal in any route is to save Rosapast.
- No Social Skills: He tries and fails to get Mina to fall in love with him in his route. Unfortunately, Mina doesn't like his forceful and forward actions.
- Sibling Yin-Yang: He's more forceful and direct with his desire to be loved by The Heroine.
- Supernatural Gold Eyes: They turn red when he tries to control Mina or take her blood.
- Tsundere: Type A. He comes across as difficult to talk to at first, but he starts showing off his dere side as he explores his route with Mina.
- Well-Intentioned Extremist: In Jack's Farewell Ending, he tries to kill Jack in order to make the player love him and save Rosapast.
- Whip It Good
A former human turned into a vampire. He is the current owner of Hotel Libra Sincera in place of his master, Harold.
- Beauty Mark: Has a small one just under the left corner of his lip.
- Parental Substitute: Acts like one to Alfred and Rupert.
- The Stoic: He doesn't seem to be that expressive. Though that might change later. Subverted as he does get angry with the player for not working.
- Not So Stoic: When Mina fails to do her chores or when defending the Rose Garden, he does emote.
- Undying Loyalty: As Harold's belonging, he's eternally faithful to his master.
The energetic and mischievous cook of Hotel Libra Sincera.
- Cute Little Fangs: Shows these whenever he smiles really big.
- Double Entendre: He can't wait to eat Mina up.
- Evil Redhead: Less evil and more mischievous.
- Knife Nut: He's often seen carrying a fork with him. He also used one in the prologue when Mina was captured. That's how he gets Mina to remember him. In Chapter 9 for Rupert's route, he uses a knife as his primary weapon.
- Mr. Exposition: Once a chapter is complete, he'll provide a sneak peak for the next one. There will be times when other characters interrupt him.
- For his route, Alfred and Rupert will provide the sneak peaks.
- Shirtless Scene: While bathing together with The Heroine. The Premium story also includes artwork showing him getting very close to her.
- Supernatural Gold Eyes: To correspond with his werewolf nature.
- The Tease: In every route, he flirts with Mina.
- Unusual Ears: He has a pair of white wolf ears and a long tail to match.
- Vampire Hunter: His real job. In his route, he revealed that he planned to make the heroine turn into a vampire so that he could capture her and sell her blood. Once he develops feelings for her, he regrets thinking about betraying her like that. In Alfred's route, she offers her blood on her own and he gets positively thrilled.
- What Happened to the Mouse?: In his Farewell Ending, Daniel runs off with him to heal his whip wounds. The story ends with the player wondering where the two of them are and if Jack is okay.
A mysterious resident of Hotel Libra Sincera.
- Apologetic Attacker: In Chapter 9 for Rupert's route, he apologizes to Mina for using her as a hostage.
- Beast and Beauty: He shares this with the protagonist in his route.
- Big Eater: The portion sizes in chapter 3 suggest he's this.
- Declaration of Protection: He makes this to the heroine.
- Icy Blue Eyes: Although he warms up to Mina during his route.
- Mr. Fanservice: Without his coat on, he has an open shirt revealing his muscular and scarred chest.
- No Sense of Direction: He gets lost pretty easily.
- Odd Friendship: With Jack.
- Scars Are Forever: He has scars on his face and body.
- The Stoic: He's mostly expressionless. However, he definitely has some When He Smiles moments in his route.
- Tall, Dark, and Handsome
- Unusual Ears: Like Jack, he has wolf ears and a tail.
Humphrey is a mysterious resident of Hotel Libra Sincera. He starts appearing during Raymond's route.
- Acquired Poison Immunity: He consumes a potion that makes his blood similar to a vampire, resulting in Mina being able to bite him without causing him to turn.
- Alchemy Is Magic: He is a wizard, but his main speciality is making potions for the guests as well as Jack and Humphrey to hide their werewolf features from the vampires.
- The Casanova: He openly flirts with the heroine.
- Really 700 Years Old: While hinted at in most routes, his route reveals that he personally knew Harold and Tatiana, making him at least 500 years old.
- Supernatural Gold Eyes: To indicate his mystical nature.
- You Gotta Have Blue Hair: Purple on top and blue on the bottom.
Dominic is the heroines childhood friend and the apprentice of Humphrey. He's currently in the forest around Hotel Libra Sincera.
- Childhood Friends: He and the heroine come from the same village and thus grew up together.
- Hot-Blooded: While a bit calmer towards the heroine, he is very temperamental, quick to anger and highly jealous. He neds up punching Humphrey during the latters route and almost kills his best friend Cedric when finding out that he is a vampire.
- Magic Knight: What he seems to aim for, considering that he is Humphrey's apprentice, yet dressed up like a warrior.
A vampire that has been sleeping in his room for many years and the older brother of Bridget. Also a good friend of Dominic, Jack and Daniel.
- Becoming the Mask: He has a few moments at the beginning of his route where he seems to have forgotten about certain vampire characteristics due to taking the human potion for so long.
- There's also the thing about him playing her boyfriend to keep her save from Alfred and Rupert, only to fall for her for real.
- Beneath the Mask: He acts very playful, carefree and flirtatious in his route except for a few moments where he becomes pushy in his aim to become heir. When he actually falls in love with the heroine, he reveals that he is insecure, lonely and only wishes for all races to get along.
- Big Brother Instinct: Though not as obvious as in most cases, he IS very protective of his little sister and cares very much about her.
- Foolish Sibling, Responsible Sibling: He appears very playful and carefree in comparison to Bridget's serious and sophisticated behaviour. It is later subverted as both become very protective and responsible to protect Mina and each other.
- Really 700 Years Old: He is a vampire and thus this applies, of course. This comes at a surprise for Dominic, Jack and Daniel though, who thought he is human.
A young vampire resident of Hotel Libra Sincera. She has an obvious crush on Alfred.
- All Love Is Unrequited: She has a crush on Alfred, but it's clear he doesn't feel the same way towards her.
- Annoying Younger Sibling: Gives off vibes of this in both Alfred's and Cedric's route as she constantly meddles with the heroine. Later in Cedric's route, she interestingly subverts Big Brother Instinct and actively tries to protect Cedric and the heroine from their parents as she recognizes that the couple is happy and good for each other.
- Beware the Nice Ones: Her character info informs you that she will try and cause trouble for you, especially on Alfred's route.
- Big Brother Worship: She has an older brother whom she admires a lot.
- Clingy Jealous Girl: She'll act like one towards Alfred.
- Foolish Sibling, Responsible Sibling: She believes to be the responsible one of the pair. Cedric's route reveals that they are both responsible, just in different ways.
- If You Ever Do Anything to Hurt Her...: In Cedric's route she first says something along these lines as a active threat to her parents who want to kill Mina. She later hints at this towards her brother as a sign that she now cares for the heroine.
- Innocent Blue Eyes: Subverted. She's anything, but innocent.
- Pretend Prejudice: Played with. In most routes she is very open about disliking Mina on the simple ground that she's a human. In Cedric's route she struggles with it though as she starts to like Mina, leading to her becoming this. In the good Cedric endings, it is hinted she might overcome her racist thoughts with Cedric's help.
- The Rival: She becomes this in Alfred's route.
- Tsundere: A non-romantic example towards the player any time a Love Challenge is completed."...I-It's not like I'm h-happy for you or anything! Now hurry up and move on!"
The Heroine of the game. She's a hunter with her Canine Companion Bernhard, short Bear. Looking for a cure for her ill sister, she wandered into the forest, trying to find the infamous vampire castle.
- Archer Archetype: Downplayed. Yes, she is stealthy, graceful, used to work alone (save for Bear) and vulnerable up close. No, she isn't arrogant and ignoring orders when given.
- Even the Girls Want Her: Bridget is usually smitten by Mina on first sight. In some routes such as Ioannis, she even starts a fight with Jack so she can have tea with her. Mina even lampshades the absurdity of it.Mina: I don't know what to do having a vampire and a werewolf fighting over me.
- Hidden in Plain Sight: She claims to be a werewolf while at the hotel to be save from the creature's hate for humans. It only works because she smells like wolf thanks to Bear. Played for Laughs when she succeeds in fooling Jack and Daniel despite struggling a lot in relating to them, yet can barely fool most other characters.
- Hunter of Monsters: Her main occupation. While she also hunts animals for food, she is mostly the protector of her village. Becomes a Chekhov's Skill in almost all routes.
The heroine's Canine Companion.
A vampire that the heroine meets in the forest. He allows her to act as his fiance in the hotel in exchange for her helping him.
- Becoming the Mask: He initially acts as the heroines fiance to force the staff to let her stay. Of course he falls in love with her soon after.
- Not So Different: He will always be on the side of the Hotel against the Organisation as he shares the hotels sentiment that all creatures are equal.
- Pretend Prejudice: Subverted. He pretends like he IS racist towards humans in his route, but he instantly knew Mina is one and doesn't care at all. In other routes, he doesn't even do that.
A young vampire resident of Hotel Libra Sincera. He is an artist and wants to become better by learning from the artwork in the hotel.
A mysterious man that is specialized in inventions. He has been tasked with producing weapons for the hotel.
- Dark Secret: He shares one with Finn, being having worked with a group of evil mages that want to rule the world with modificated beasts. It also leads to his werewolf condition, causing him and Finn to run away.
- Gadgeteer Genius: His job, though his specialisation is in weapons.
- Odd Friendship: With Finn.
- Our Werewolves Are Different: In opposite to Jack and Daniel from Season 1, he always fully transforms into a wolf.
- You Gotta Have Blue Hair: His is a purple-red. When in wolf form, his fur is purple-red, too.
A mage that often interacts with Gordon.
- Dark Secret: He shares one with Gordon, being having worked with a group of evil mages that want to rule the world with modificated beasts. It also leads to Gordons werewolf condition, causing him and Gordon to run away.
- Friend to All Living Things: He is a mage who is tuned on interacting with the spirits of nature and thus in general a friend of everything with a soul. Doesn't stop him from being a Jerk with a Heart of Gold though.
- Jerk with a Heart of Gold: While he is this most of the time, he increases the Jerk part when interacting with the heroine in Gordon's route.
- Odd Friendship: With Gordon.
A mysterious masked man that seems to be able to sense the future by looking at people.
- Career Versus Man: He has to decide between fulfilling his duty of killing Mina or letting her live. He tries to Take a Third Option, the outcome deciding on the Ending.
- Dark Is Not Evil: He runs around in a dark coat with mask, acts suspicious and mysterious and often spends his time telling Mina she might or will die soon. He is telling her as a warning though in an attempt to ensure she will avoid that fate.
- Face Death with Dignity: He wants to grant Mina this by letting her live until the Hotel is safe. For bonus points, not taking her life before the day is over would end his own. And he would be fine with that as well.
- The Grim Reaper: He and his brother are "Angels of Death".
- Love Makes You Crazy: He risks more than just his job when he falls in love with Mina.
- The Spock: He has no emotions and acts very passive. That is, until he is hit with First Time Feeling when he falls in love with Mina.
A beautiful vampire lady and guest at Hotel Libra Sincera. She quickly becomes protective and friendly towards the heroine and supports her in all routes.
- Beauty Equals Goodness: While applying to all characters to some extent, she is one of the very few that never does anything bad to anyone.
- The Beautiful Elite: She is absolutely stunning, her dress and behaviour are typical of the higher class and most characters refer to her as "Lady Bridget". She isn't bragging about it in any way though and treats everyone as her equal.
- Even the Girls Want Her: Though not an option, there are hints that Mina fully recognizes Bridget's beauty and appeal and she often blushes when Bridget hugs her.
- Gorgeous Period Dress: Wears a outstanding red dress.
- If You Ever Do Anything to Hurt Her...: Treats almost every suitor of the heroine with this, once she gets attached to Mina.
- Onee-sama: She is beautiful, ladylike and respected by all characters. The heroine usually looks up to her and Bridget returns it by feeling the need to be protective of her.