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The lead female protagonist and heroine of The Wonderful Wizard of Oz. She's currently residing with her Aunt Em and Uncle Henry.
- Hello, [Insert Name Here]: Like any other Shall We Date? heroine, you can change her name.
- Iconic Outfit: Despite the game being based on the books, the outfit Dorothy wears in CGs and promotional material is obviously based on Judy Garland's iconic dress from the film.
- The Ingenue: Sweet, young, and innocent to the point where most of the (intentional) flirtations directed her way go over her head.
- Innocent Blue Eyes: Dorothy's canon appearance and default eyes, though this can change in the dress-up portion of the game.
- Oblivious to Love: Dorothy either misses the romantic signs completely or doubts that they were intentional until her love interest confesses outright.
- She Cleans Up Nicely: Dorothy's cute, of course, but the guys have this response after she changes into a fancy gown for the ball.
- She Is All Grown Up: Invoked by the love interests, as Dorothy was a little girl the last time they saw her.
- Wide-Eyed Idealist: Although she handles more serious issues like her part in the rebirth of Oz better than most such Idealists do.
The Scarecrow with a human body. Since Oz left the kingdom, Crowlie has been crowned king of the Emerald City. With a little magic from Solomon, he's granted a human body with a human heart. Upon reuniting with his long-lost friend, he hopes to win her heart.
The Lion with a human body. With the courage granted to him by Oz, he has been able to reign over the forest without hesitation. Thanks to Solomon's magic, Leonardo feels more comfortable getting close to the girl he loves.
- Big Eater: Has a, well, lion-like appetite.
- Cowardly Lion: Not anymore, despite being the Trope Namer.
- Fearless Fool: To the point where, as things get more serious, others accuse him of being too dense to understand how serious everything is.
- Keet: Very energetic and lively.
- My Instincts Are Showing: Leonardo is initially unable to control his animal urges and subsequently gets too aggressive with Dorothy in his route.
- No Sense of Personal Space: Leonardo loves to Glomp Dorothy and, thanks to being newly human, often forgets that personal space is a thing. This extends to his other friends, as in Wesley's route when they aren't able to go on a date with Dorothy and Leonardo cheerfully suggests that he, Crowlie, and Heartmann take a nap together.
- Punny Name: "Leo" is another term for "lion".
- Raised by Wolves: Well, he was a lion until very recently.
- Too Hungry to Be Polite: Leonardo seems to eat like this as a matter of course.
The Tin Man with a human body. Heartmann is more than willing to give his beloved all the love in the world. However, he seems to be keeping something important from her.
- Hair of Gold, Heart of Gold: He might not have a literal golden heart, but he's possibly the nicest, sweetest-natured character in the cast.
- Perpetual Smiler: He's almost always seen with a pleasant smile on his face.
- Prone to Tears: Played for Laughs, as he's often moved to tears by minor things.
- Punny Name: It looks like "Hartman", but with an "e" in the beginning to emphasize his heart.
- Wide-Eyed Idealist: Almost as much as Dorothy.
The Wizard of the West. Ever since his defeat, he's developed quite an interest in the young heroine. He hopes to get close to her and show a different side of him that no one else knows about.
- 0% Approval Rating: Even though he's changed, no one trusts him.
- Be All My Sins Remembered: He knows he did terrible things in the past and he's not comfortable glossing over it, even if the others persuade the masses that he's changed.
- Break Her Heart to Save Her: Tries to do this to Dorothy in his route. It doesn't work.
- Dark and Troubled Past: Not quite on part with Wicked, but it's definitely both dark and troubled.
- Dark Is Not Evil: He's a changed man since the events of The Wonderful Wizard of Oz. If he wasn't, then he wouldn't be a love interest.
- The Dreaded: As the Wicked Wizard, of course.
- Emotionally Tongue-Tied: When he tries to admit his feelings for Dorothy, or to say nice things in general, Wesley has a hard time getting anything out.
- Eyepatch of Power: He can use his right eye for divination; the eyepatch he wears is able to block that power for his everyday life.
- Gender Flip: Of the Wicked Witch of the West.
- Heroic Sacrifice: Towards the end of his route. Everyone is shocked and Norton ends up having to resurrect him again.
- Hidden Heart of Gold: He's really not a bad guy, at least post-resurrection.
- Insufferable Genius: He's extremely proud of his magic and doesn't hesitate to bring it up.
- Jerkass Woobie: Once you find out about his backstory.
- Loony Friends Improve Your Personality: Thanks to Dorothy and the rest of the main cast, Wesley slowly opens up.
- Mark of the Supernatural: He has one red eye, usually covered by an eyepatch, and one black eye, formerly a black eye of evil.
- Multicolored Hair: His black hair shades to white/gray at the ends.
- Parental Abandonment: Wesley spent his earliest childhood in an orphanage, having been left there by his mother.
- Punny Name: Wesley sounds like West, as in, The Wicked Witch of the West.
- Spared by the Adaptation: Of a sort; while he was defeated during Dorothy's journey, Solomon brought him back to life for a chance at redemption.
- Trash Talk: Engages in this frequently, usually directed to the "Three Stooges" of Crowlie, Leonardo, and Heartmann.
- Tsundere: He becomes this as he softens up towards Dorothy and the cast, trying to hide it and insisting that he's an "evil sorcerer."
- Used to Be a Sweet Kid: Implied after Dorothy finds the photo from Wesley's childhood.
- Weaksauce Weakness: Water, just like in the original.
The consummate showman with a love of hot air balloons, Oz has been called back to Oz to celebrate Dorothy's birthday. He seems to have an agenda of his own.
- The Atoner: Returns to Oz primarily to make up for accidentally leaving Dorothy behind the first time they were in Oz.
- Attention Whore: A benign form, but he's definitely at home in front of a crowd and is more than happy to show off at the drop of a hat.
- Berserk Button: Don't you dare imply that stage magic is nothing but worthless tricks.
- The Charmer: Not only with Dorothy, but he flirts playfully with random NPC townswomen.
- Chivalrous Pervert: A mild version, in that he's the love interest most likely to make deliberate moves on Dorothy and be open with his flirting, but of course he veers strongly towards Chivalrous nonetheless.
- Deadpan Snarker: In contrast to Wesley's Trash Talk. Oz also directs this towards Wesley as often as towards Crowlie, Leonardo, and Heartmann.
- Florence Nightingale Effect: A turning point in his relationship with Dorothy comes when she takes care of him after he's injured and falls ill.
- Genre Savvy: Knows from the start that there's more going on than just Dorothy's birthday.
- Loony Friends Improve Your Personality: It's not so much that they get him to loosen up as they convince him to believe in The Power of Friendship.
- The Magnificent: He's "The Great Oz," after all.
- Nice Hat: A green top hat.
- Older and Wiser: He's not that much older, especially compared to the wizards, but Oz fills this role in the main cast as the older and more worldly guy.
- Sharp-Dressed Man: Complete with Waistcoat of Style.
- Snake Oil Salesman: His former trade, though it's only occasionally mentioned or alluded to.
- Stage Magician: And proud of it!
The Wizard of the North, second in power only to Solomon. Acts mostly like a servant and assistant to him, though he ocassionally takes a stand against him as well.
- Anywhere but Their Lips: In his route, he will often give Dorothy a "charm" aka a kiss on the forehead. He did it on her previous journey as well.
- Bad Dreams: He rarely - if ever - sleeps since he suffers from this. It's his payment for his powers, each spell making him more tired while increasing the horror of his nightmares.
- Evil Is Deathly Cold: He is ruler of the frozen north and acts like this in his, Solomons and Wesleys route.
- First Girl Wins: In his own route. In some of the others, he will question why it isn't the case since he had kissed her in her previous journey.
- Hidden Agenda Villain: In Wesley's and especially Solomons route, he is.
- Ice Queen: He sees himself as this, especially in his own route. Dorothy is able to melt his heart though.
- Jerkass Woobie: When he isn't The Stoic, chances are he is this.
- Stepford Smiler: Though he doesn't always smile, in almost every route Dorothy will mention at least once that his smile doesn't reach his eyes. He gets worse in his own route before getting better in the ending again.
- The Stoic: He does smile, but his demeanor is mostly very unemotional and cold.
- Well-Intentioned Extremist: He and Solomon both simply want to save the Land of Oz. But while Solomon is simply waiting for how everything plays out, trusting that any result will be fine, Norton is very eagerly trying to keep Oz exactly the way it is.
Lord Solomon is the Wizard of the South, the most powerful sorcerer in Oz as well as its de facto ruler. He's responsible for bringing Dorothy back to Oz and hosting her birthday celebrations.
- The Ace: He's the most powerful wizard, a kind and just ruler, a monarch beloved by all, and an amazing dancer.
- The Archmage: Solomon is apparently the most skilled wizard around and frequently performs a wide array of magic with little more than a thought or a wave of his hand. The only magic that he can't perform himself and thus needs the help from Norton is resurrection magic.
- Asskicking Equals Authority: He's the strongest mage in Oz and appears to be its acting ruler.
- Gender Flip: Of Glinda, Good Witch of the South.
- Pointy Ears: Apparently a trait of Oz natives, wizards, or both.
- Power Crystal: Both the source of his magic as well as his major weakness. Since it resides in the basement of Quadling Castle, he isn't able to leave the castle without losing most of his powers and shattering the crystal would instantly kill him.
- Reasonable Authority Figure: As the apparent ruler of Oz, he's as fair as he can be and listens to the concerns of the rest of the cast, doing what he can to alleviate their fears.
- Sage Love Interest: If you play his route, he spends the early portion acting more as a kind counselor than an outright love interest.
- Shipper with an Agenda: Serves this role in all routes but his own, given that he wants Dorothy to find a boyfriend and save Oz from destruction.