Liz Hart is a young orphan with a love of animals and a somewhat unreliable talent for magic. Though she dreams of becoming a skilled wizard and using magic to bring smiles to the faces of others, more often than not she can't manage to get even basic spells to work right. She's surprised and elated, therefore, when she receives an invitation to Gedonelune Royal Magic Academy, a prestigious Wizarding School with a long history.
When she arrives, however, she learns that her acceptance as a student at Gedonelune is only on a provisional basis. She has two weeks to prove that she has what it takes to be formally accepted as a full-time student - a daunting task for a girl who's had to teach herself everything she knows. She'll have to rise to the challenge to pass the test, discover the secrets of Gedonelune, and find love with one of her fellow students.
Shall We Date? Wizardess Heart includes examples of:
- The Ace: Klaus Goldstein is the prefect of the school and good at pretty much everything, from magic to sports to making tea.
- Always Second Best: Elias Goldstein struggles to live up to the standards of his famous family, especially the example of his older brother Klaus. Although Elias is a genuinely skilled wizard, Klaus observes that he lacks imagination, and comes down hard on him in an effort to inspire him to improve.
- An Arc: The various routes of the game are grouped into story arcs dealing with a particular mystery. Elias, Yukiya, and Luca's routes make up the "Tower of Sorrow" arc; Klaus, Randy, and Azusa's routes comprise the "Spring of Unicorns" arc; and Joel, Vincent, and Leon's routes make up the "King of Fairies" arc. The details of the mystery and its full context are scattered across the three routes of each arc, so that while each individual route may be self-contained, the player only has the full picture if they play all three routes.
- The Big Damn Kiss: Every happy ending route has one, as expected of a dating sim.
- Big Man on Campus: Although overshadowed by his brother, Elias is very successful in his classes and popular around the school, with quite a few female admirers. He can be a little stuffy, but overall Elias is helpful and conscientious toward the heroine and their other fellow students, and was the only person willing to be Yukiya's roommate when everyone else refused for fear of being cursed.
- Brilliant, but Lazy: Luca is a gifted wizard, but hates doing work and constantly skips classes due to finding them "boring."
- Chekhov's Classroom: The school's professors frequently teach plot-relevant lessons to the class, with all the subtlety of dropping an anvil on the protagonist's head.
- Crossover Cosmology: Several magical creatures from many different mythologies appear. Chimeras, unicorns, nue, fairies, and even a half-human kitsune appear in this world! On top of that, there are a few creatures (such as Carbuncles and Wing Rabbits) that are original creations.
- Dark and Troubled Past: Being the bastard child of the princess of Gedonelune, Luca was taken away from his mother by her close companion Conrad Schuyler, and was locked in a cellar for most of his early life. He was only allowed outside once he was old enough to attend the academy, but this was effectively another prison in his eyes, as he was not allowed to leave. This is also implied to be the reason he wants to escape the school to travel around the world.
- Defence Mechanism Superpower: The protagonist has the ability to bend time, but due to her weak magic and control, this power is only harnessed when she or someone she loves is in danger.
- Disguised in Drag: Because their male children are at risk of being abducted by leanan sidhe for the rare magical talent that runs in their bloodline, the Crawford family of spellsingers disguise their young boys as girls until they are old enough to be out of danger. Joel Crawford was disguised as a little girl named June when he met and befriended the protagonist as a child, and she doesn't learn the truth until they meet again as teens.
- Familiar: Wizards have the option of having these as companions, and can use them to harness magical abilities. They can also see and speak through their familiar.
- Klaus visits the protagonist with his owl familiar in his route.
- In Luca's normal ending, Luca is allowed to leave with the protagonist under the agreement that he is monitored by Professor Schuyler through his familiar. Much to Liz's surprise, Schuyler's familiar is a cute black cat.
- The headmaster also has a familiar: a rare pink carbuncle.
- Fantasy Counterpart Culture: Hinomoto, the country that Azusa Kuze hails from, is a fantasyland version of feudal Japan. This is reflected in Azusa's clothing and in his use of Onmyōdō in place of the wand-and-incantation style used by most Gedonelune wizards.
- Glenn Qing comes from a fantasyland version of feudal China.
- Hiro Tachibana has Hinomoto heritage.
- Hisoka Hagakure, who is half-kitsune, is also from Hinomoto.
- Forced Transformation: During Elias's route, Elias suggests that the protagonist try casting a spell to make him taller after she mentions that the magic she casts on animals usually works. She accidentally turns him into a piglet. It happens again in the Goldstein brothers path of the "Battle Mode in Love Sandwich" side story when the protagonist tries to cast a healing spell.
- Forgotten First Meeting: In the "King of Fairies" arc, the protagonist and Joel Crawford were close friends as children and promised to attend the magic academy together when they were older. However, not only has the protagonist forgotten all about it until she arrives at the academy, she knew Joel as a little girl named June, so even when she does begin to remember it takes several days before she begins to put the pieces together. Late in the route, she learns that she forgot because Joel used magic to suppress her memories of their friendship so that she wouldn't be sad when he had to move away.
- Gender Bender: Headmaster Randolph turns into a beautiful red-headed woman at night, as the result of a magical contract.
- Girlish Pigtails: The protagonist wears her hair in twintails. Klaus, noting the resemblance to rabbit ears, takes to calling her "Bunnyhead."
- Handsome Lech: Luca. Noted to be quite good-looking by the protagonist and other students, he is also a shameless flirt. The protagonist is even advised by her roommate Amelia to stay away from him for this reason.
- Inept Mage: The protagonist's magic rarely works the way that she wants it to, even after she begins taking classes at the magic academy. Most of her attempts to cast spells misfire comically; much of this is chalked up to lack of concentration on the protagonist's part, but it happens so often and so dramatically that Klaus speculates that she has some kind of rare talent that she simply hasn't been able to make proper use of. His theory is proven on several of the routes which show her demonstrating uncommon magical abilities or unexpected levels of power, such as time travel, spellsinging, or the ability to perform magic with words alone.
- The Ingenue: The protagonist is painfully innocent and naive, a characteristic which is frequently taken advantage of by the more morally ambiguous characters.
- Jerkass: Luca. In Yukiya's route, he drags a very sick (and barely walking) Yukiya through the forest so he can complete his quest to find the Tower of Sorrow, ignoring the protagonist's pleas. They later battle in the forest, though whether he would've killed Yukiya to get his way is unstipulated. He also attempts to kill Professor Merkulova in Elias' route, though it is unclear whether he was really going to go through with it, or was just putting on an act because he knew the protagonist would stop him.
- Jerk with a Heart of Gold: Another interpretation of Luca. While he acts like he doesn't care about others, and repeatedly does things to hurt/confuse the protagonist, it is implied that he is trying to push her away so as to not feel bad about leaving Liz and the academy after obtaining the dragon eye. This is further proven by him giving the dragon eye to the Mysterious Beauty when Liz is threatened with danger. Taking into account his behaviour in other routes, it is probable that this heart of gold is brought out by his relationship with Liz.
- Jigsaw Puzzle Plot: Because of the way that the routes are divided into story arcs, the only way to get the full story with all relevant context is to play all three routes within the arc. Each route can be played on its own, but without completing the arc it won't be clear why, for example, Luca Orlem is acting as the antagonist of Elias and Yukiya's routes, or why Klaus speaks so derisively about Serge Durandal when the protagonist mentions wanting to be like the legendary magical beast tamer early in Klaus's route, or why Azusa Kuze is using dark magic and searching for the unicorn spring.
- Lampshade Hanging: One about dating sims, and reverse harems in general.Liz Hart: Why is everyone who goes to this school so good-looking?!
- Magic Music: Spellsingers are wizards with the rare talent for casting wandless magic by singing. Joel Crawford in the "King of Fairies" arc is a spellsinger.
- Manipulative Bastard:
- Luca is very eager to and successful at manipulating the people around him, the most prominent example being his using of Professor Murkoluva and the protagonist to bring him to the Tower of Sorrow.
- In "The Performing Festival," Klaus's spin-off story, he purposely gets the protagonist in trouble for speaking in class so that Schuyler will give her a part in the school play as punishment. Then he gets himself in trouble (or rather brings up all the times he's caused trouble), and is appointed director as his "punishment."
- He frequently uses a pillow to make a doppelganger of himself to attend class for him, to the point where Professor Schuyler can recognize the ruse almost immediately.
- In Klaus's route, Luca tells the protagonist a "spell to make people act nicely." It creates a giant pink toad on top of Klaus's head.
- In the side story "The Performing Festival," Luca gets Professor Schuyler to make him the director of the play. It goes exactly as you would expect it to.
- Mayfly–December Romance: Liz and Leon, due the latter being a unicorn.
- The Mirror Shows Your True Self: The Persona Mirror is a Magic Mirror enchanted to reflect a person's true self. When Elias looks into it, it reveals his insecurities and his frustration about having to live up to his family's legacy. When the protagonist looks into it, however, it shows that her outward self and her inner self are exactly the same.
- Mix-and-Match Critters: Chimeras and Nue!
- Mystical White Hair: Leon's white hair (and red eyes) serve to highlight his mysterious and otherworldly nature; he turns out to be a unicorn.
- Nue: Yep. And they're terrifying.
- Our Werewolves Are Different: Yukiya turns into a horned, fanged, black beast whenever his cursed eye looks upon the full moon. This is the product of a contract Yukiya made with his wolf companion to save his village when it was under attack. This contract is also the source of his magical power, and the reason he came to despise magic.
- Punny Name: The main character's default name is "Liz Hart," and she is an aspiring wizardess... which is to say, she hopes to become Wizardess Hart.
- Really Royalty Reveal: Luca is the bastard child of Princess Aulelia of Gedonelune. His real name is Luciano Orudeus Gedonelune.
- Sadist Teacher: Klaus claims that he wants to be a teacher in order to yell at students when they mess up, claiming they'd be like stress balls. His route makes it clear that he's exaggerating, however, and although he's a harsh taskmaster he's actually a good teacher who puts a lot of thought into adapting his teaching methods to what will best serve his students.
- School Idol: Prefect Klaus Goldstein is the most famous and influential student at Gedonelune. His fellow students call him "the Emperor," and he has enough status around the school that he's treated more like a teacher than a student, even occasionally teaching classes when the professors need a substitute.
- School Play: A school play features in the side story "The Performing Festival," with the protagonist and Elias stuck unwillingly in the lead roles and Luca enjoying himself far too much as the director. Shenanigans result, particularly after the protagonist and Elias learn that they're expected to perform The Big Damn Kiss at the climax of the play.
- Shipper on Deck: Liz's roommate and friend, Amelia, will happily support Liz and her selected love interest.
- Stern Teacher:
- Professor Conrad Schuyler defaults in manner to blunt and sardonic; he's quick to criticize his students' failings, and reacts with exasperation to the protagonist's repeated magical mishaps. Given what he has to put up with on a daily basis, it's hard to blame him.
- Klaus, though still a student himself, is also well on his way. On his route, he appoints himself the protagonist's personal drill instructor with the object of making sure she passes her acceptance trial, and though he's a merciless taskmaster he genuinely wants her to improve and puts a lot of thought into what methods of instruction would help her the most. Despite being promised a position in the Bureau of Magical Justice on graduation, when Headmaster Randolph suggests that he could instead become a teacher, Klaus reacts with the open glee of someone who's just been offered the keys to the candy store.
- Surprisingly Creepy Moment: Azusa's route definitely qualifies. Not only does he show his true villainous nature after a somewhat sweet beginning, but there are scenes where the player can have Liz tell him about the earrings—and he summons a Nue that LITERALLY KILLS HER. She gets resurrected and sent back in time, but still, daaang.
- Technician vs. Performer: Elias has studied and trained intensively, developing flawless technique to make up for what he feels is a lack of natural talent. Luca, meanwhile, has a lot of ability but skips class more often than he attends and uses magic irresponsibly. Unsurprisingly, the two are often at odds. Comparing them, Klaus criticizes Elias for being too by-the-book and pushes him to be more inventive, noting that Luca's magic has a creativity to it which Elias lacks, and pointing out that it's only via innovation and experimentation that magic can grow and develop.
- Tongue-Tied: The protagonist has a spell cast on her by Azusa that renders her unable to speak the truth about him. He also prevents her from saying the words "I love you."
- Two-Teacher School: The player only ever sees three members of the school's faculty: Headmaster Randolph, Professor Schuyler, and Professor Merkulova - and even Merkulova doesn't appear in all routes. The only other school staff mentioned is the protagonist's nameless, spriteless dorm mother.
- White-and-Grey Morality: Even the villains in this universe are at least somewhat sympathetic, though it can get dark sometimes. This is most pronounced in Azusa's route.
- Wizarding School: Gedonelune Royal Magic Academy is a school for the training of wizards. It even has a Snape Expy in the person of Professor Schuyler.
- Youkai: A few appearances. There are the creepy Nue, and there is also Hachi, a talking dog youkai who is Hisoka's familiar. Hisoka himself turns out to be half-kitsune.
