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Tora Igarashi
Do not let that Gentlemanly smile fool you.
Voiced by: Kenichi Suzumura (Japanese), Andrew Love (English)
Student council president of the high-class and expensive Miyabigaoka Academy. He initially presents himself as a gentleman who admires Misaki's reforms at Seika and offers her a scholarship to Miyabigaoka, but it's quickly revealed that he's a lecherous young man who's used to being able to manipulate people thanks to his wealth and his family's high social status. He also seems to be familiar with Usui's background.
- Always Someone Better: To Misaki in martial arts skills. As skilled as Misaki was in using Aikido to defeat most men, Igarashi knew Judo and had an even better sense of ground game which enabled him to easily overpower Misaki.
- Arch-Enemy: To both Misaki and Usui.
- With Misaki, It's Personal. There have been plenty of other male characters who have either tried to rape or harass Misaki in the past like the Three Idiots, Kuuga, and the two guys who broke into Maid Latte one night to tie up Misaki. However, Misaki hates Igarashi more than any of the others and always sees him as the biggest threat.
- With Usui, Igarashi is almost like Foil. The two of them are respected by their peers, rank at the top of their class, beloved by the girls at their school, skilled in martial arts, and come from rich families. After that, however, the similarities end. Unlike Usui, Igarashi is not a kind soul and is thoroughly rotten enough that he'll try to take what he wants through force, bribery, or other unscrupulous methods. And whereas Usui doesn't call attention to his rich background, Igarashi isn't afraid to flaunt or take full advantage of his family's riches. In short, Igarashi is everything Usui would be if Usui allowed his Ace status and riches to go to his head and become thoroughly corrupted.
- Attempted Rape: Tries to pull this on Misaki.
- Big Bad: Arguably one in the early arcs of the story, particularly during the Footman arc. Subverted in the Britain arc where he basically becomes the Jerk with a Heart of Gold.
- Curtains Match the Window: Bright gold hair and eyes.
- Defeat Equals Friendship: He loses out to Usui when it comes to winning Misaki over. Also, they have a physical fight later on and while Igarashi wasn't exactly beaten to an inch of his life, it was still pretty apparent that Usui was the superior combatant who had him beat at the end. After this, the two of them apparently get on much better terms over the years to the point where during Misaki and Usui's wedding, it's revealed that he's been helping out Usui with offscreen matters.
- Easily Forgiven: Okay, so he wasn't "easily" forgiven in the conventional sense as it isn't until much, much later in the story that he stops being an outright antagonist to Usui and Misaki. And he and Usui would eventually come to blows towards the end of the series. However, it's still saying something that Usui gets on friendly terms and becomes something resembling casual business acquaintances with the guy who once tried to rape his future girlfriend and wife. Granted Igarashi did help Usui out in a big way by helping reunite Misaki with him late into the story but even then, Usui repaid the favor by helping Igarashi fight off some goons sent to beat him up... he didn't need to continue hanging out with the guy who tried to rape Misaki after all that.
- Everything but the Girl: Has the wealth, the influence, and the swag, and yet he could not sway over Misaki's affections for Usui.
- Evil Counterpart: To Usui. Like Takumi, he's The Ace at everything, excelling in school, being a martial arts expert, attracting most of the girls at his school, and coming from a rich background. Unlike Takumi, he's a Smug Snake and a pretty rotten guy.
- Forceful Kiss: Gives one to Misaki after arriving from Britain. In full view of Usui.
- Hidden Depths: Plays Tennis.
- I Love You Because I Can't Control You: The reason why he sees Misaki as a step above the other women he's met.
- Jerkass: His introductory arc portrayed him as this, particularly when he tried to force himself onto Misaki.
- Knight of Cerebus: His presence doesn't make the story excessively dark but by the standards of a Romantic Comedy anime, he's probably treated as the most serious antagonist in the story, being willing to commit the most open form of Attempted Rape. And though Misaki gets into plenty of conflict with other men who harass her or have bad intentions for her, Igarashi is treated more seriously than them because while Misaki can mostly handle those other men, she most definitely can't handle Igarashi and needs Usui's help to deal with him. And in final contrast to all of Misaki's other male antagonists, Igarashi's presence tends to draw out more fear and revulsion from her than any other foe and it's a something that never really goes away until the end of the series.
- Pet the Dog: Decides to help Misaki in her quest to be reunited with Takumi in England.
- Student Council President: Of Miyabigaoka. Like his Seika High counterpart, retires from his post in the final few chapters.
- Ungrateful Bastard: At one point he's attacked by some men sent to beat him badly. Takumi actually comes by and helps him fight those men off. What does Igarashi do? He decides to take a swing at Usui and then try to claim it was an accident, which leads to the two of them getting into a fight. Keep in mind, this was already after Igarashi had kissed Misaki in front of Usui, which could only pour more gasoline on an already-raging fire and make Takumi want to beat him up even more.
- Villainous Crush: Towards Misaki.
- Wake-Up Call Boss: For Misaki. She finds out for herself that he's the first antagonist she's gone up against who can't be overcome with her strong personality, martial arts, or a rousing speech.
Maki Kanade
Voiced by: Tomoaki Maeno (Japanese), Jack Ivy (English)
The vice president at Miyabigaoka High.
- Beneath the Mask: See Hidden Depths.
- The Dragon: To Igarashi.
- Eyes Always Shut: It's very rare for him to show his eyes whenever he appears in the story.
- Hidden Depths: Is legitimately touched by Misaki's speech about helping others in the cafe.
- Noble Top Enforcer: To Tora, as Miyabigaoka's Vice President.
- Perpetual Smiler: He's almost always seen smiling.
- Undying Loyalty: Maki shows great loyalty towards Tora and tries to think of the best for him.
Hirofumi Koganei
The president of Miyabigaoka's Chess Club, and the first character of the said school whom Misaki and co. encounters in the story. Ends up as Usui's classmate when the latter transferred there.
- Arc Villain: Basically his role in the series, paving way for Miyabigaoka's involvement in the story.
- Jerkass: His first appearance has him berating a couple of Seika high students for merely admiring a chess set in display.
- Put on a Bus: Twice. First was after Usui defeated him in Chess; then later after the introductory arc for the rest of Miyabigaoka's elite upon Usui's transfer.
- Sanity Slippage: Completely lost it in Chapter 83 when he hired thugs to roughen up both Usui and Tora (and possibly Misaki, if the conversation of the thugs during the center test is to be believed). Tora definitely went his way with getting payback afterwards.
- Villainous Breakdown: Upon losing to Usui in an impromptu Chess game.
Kanon Umekouji
One of Takumi's new classmates, and Tomu's twin sister.
- Berserk Button: Don't insult her bear.
- Girls Love Stuffed Animals: Is never seen without her bear, Edward.
- Sibling Yin-Yang: The Hot-Blooded yin twin to Tomu's Cool-headed yang.
Tomu Umekouji
Kanon's older twin brother, who's also trying to befriend Takumi.
- Big Brother Bully: He enjoys tormenting his sister.
- The Faceless: His hat is almost always covering his eyes.
- The Slacker: While Tomu takes her responsibilities seriously, he’s known to slack of do to his lack of competitive spirit.
- Sibling Yin-Yang: The cool-headed yang twin to Kanon's Hot-Blooded yin.
Ichitarou Tomikouji
The Umekouji twins' childhood friend.
- Childhood Friends: As stated above, he's this to the Umekouji twins.
- Curtains Match the Windows: He has short spiky dark hair and dark eyes.
- Motor Mouth: And it irritates people, particularly Kanon.
- The Voiceless: Subverted. Due to his annoying Motor Mouth, Kanon makes him speak via the tablet he is holding.
Tenryuu Arashiyama
Another student who's trying to befriend Takumi. He is obsessed with fashion and is Lin's fiancé.
- Crazy-Prepared: Keeps makeup supplies underneath his shirt.
- I Want My Beloved to Be Fashionable: Wanted to change Lin's plain look and as a result became obsessed with fashion.
- Mad Artist: Can basically make any girl very beautiful within a short period of time, despite acting like a complete pervert.
- Mundane Made Awesome: In the form of a Badass Bandolier loaded with beauty products.
- The Makeover: His specialty.
- Perfectly Arranged Marriage: With Lin.
- The Stoic: Normally.
- Not So Stoic: When fashion is involved.
Yi Hua Li
Another student who's trying to befriend Takumi. She is also Arashiyama's fiancée.
- Anime Chinese Girl: Lineage-wise, since she's the only daughter of a Hong Kong billionaire. Appearance-wise, not so much.
- Beautiful All Along: Yes, that is the same person.
- Perfectly Arranged Marriage: With Arashiyama.
- Single Woman Seeks Good Man: When asked why a beauty like her was with Tenryū, Yi Hua reveals that it was due to the effort he put into making her beautiful, knowing herself to be his masterpiece.
