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Yes, this game is unflinchingly dark, but it's not without its heartwarming moments, either.

Base Game

  • After everything they've been through in the previous game, it's quite touching that Sugiura would band together with Tsukumo to start a detective agency of his own, having been inspired by Yagami himself. He and Tsukumo even let Yagami and Kaito treat their office as their own hideout while in Yokohama, too.
    • It's especially touching when you remember that Sugiura himself was also an introvert and shut-in like Tsukumo before his sister's death, so to see the two have plenty in common with each other while working together to pursue detective work is quite uplifing to see.
  • Yagami, Kaito, and Sugiura posing as students in the classroom via hidden microphones, all stand up for Koda while encouraging the rest of the students present to also take a stand against Matsui, Sakaki, and Akane for their abhorrent behavior towards Koda. Pragmatically speaking, Yagami had little reason to do this, but he did it because it was the right thing to do.
  • Yagami's brief, but reassuring You Are Better Than You Think You Are speech to Koda where he not only supports her decision to quit the basketball team, but to also pursue the sport on her own terms, without their involvement.
  • The School Stories also have moments as well:
    • The finale of Boxing Story has Kenya being offered to join the pro circuit.
    • The final mission serves as one huge Call-Back to the "Golden Mouse" side story. In it, after Itokura leaves with Koga, Yagami gathers all the students and people he helped during the School Stories to help find her. Everyone contributes, from the Robotics Club stealing Koga's gun to the members of the Boxing Gym and Biker Gang handling the goons. Even the Rabbits get their time by locating Itokura.
    • And in the end, Itokura tells her victims that she will leave Seiryo High as atonement for what she has done as the Professor. But the other students beg her to stay, saying they're at fault too for what happened at the Cultural Festival and they apologize for what happened. Itokura breaks down in tears as she realizes she had friends all along.
    • It's all made a lot more heartwarming considering the reason why Yagami seems so gung-ho about helping Seiryo High's clubs beyond trying to investigate a larger overarching mystery. When he's first introduced to Itokura, Tak sheds a bit of light in that he "became an adult without enjoying how to be a kid" - calling back to how he dropped out of high school after his parents were murdered. He admits that he doesn't want anyone to miss out on being able to enjoy such formative and enjoyable years of their life, and combined with a later statement from Amasawa teasing him over partaking in various social activities since joining Seiryo High as faculty, the amount of clubs he joins and the skills he picks up from them can be interpreted as Yagami enjoying the School Stories to actually make up for what he missed out on as a teenager too.
  • In a mix of both awesome and heartwarming, as the YDA start rushing to get to the Final Boss stage, they're assaulted by the RK which they take care of quickly. But just as they're done, the police start closing on them as well. The gang prepares for another long wave of fights as they lose more time, before Detective Watanabe, the former bully gang (Matsui, Akane, and Sakaki), and the Yokohama Liumang all turn up in their Big Damn Heroes moment to hold off the police so that the YDA can make their escape. Given that all of them were on antagonistic terms with Yagami and the YDA at some point, it's touching to see them all teaming up to help their previous foes.
    Kaito: Heh, looks like everybody's on our side. Except RK and the cops.
  • Combined with Tear Jerker, but in the ending, after Reiko turns herself in, she calls her son and tells him she won't be coming home anytime soon. Despite everything, Mitsuru tells her he managed to start walking again and he will support his mother in her time of need.
  • Also in the ending, in a case of Book Ends, we see a girl being harassed by some bullies when several other Seiryo High students, including Koda and the reformed bullies, finally stand up to them, forcing the bullies to leave. As the girl starts crying, Koda reassures her everything will be okay. Looks like Seiryo High is gonna be fine after all.
  • The ending credits features our main five characters hanging out together.
  • "Curse of the Amasawa Family Heirloom" is both a heartwarming and awesome moment for Amasawa. She's spent the last seven years haunted by the events surrounding the seemingly accidental and supernatural events surrounding her grandfather's death and her decision to run and hide instead of help him. However, with Yagami's help she's able to finally put that particular ghost to bed while also being the one who's able to figure out the lucky cat's secret and how the murderer used it to make her grandfather's death seem like an accident. Even though they got off on the wrong foot, by the end of the case it's clear that Yagami has grown to respect Amasawa's ability as he praises her for being the one to solve the mystery and tells her that her grandfather would be proud of her.
  • The Biker School Story is full of this. Seyama tells Yagami that most of those bikers are crying out for help with their reckless racing, and he makes sure that the leaders of each faction get their happy endings after Yagami bans them from doing death races.
    • Hanasaki is a disowned son of firework artisans who lives in the street and tries to have a relationship with a girl from a wealthy family, whose parents disapprove of their relationship. After racing him, Seyama brings Hanasaki's estranged father, who compliments his son's pyrotechnics skills, which prompts both father and son to reconcile. In the end, Hanasaki cleans up his act and is even given permission to date his girlfriend.
    • Rina has deluded herself that if she dies in a race, she can be with Reiji Murasaki. Both Yagami and Seyama manage to relay the last words Reiji had for her, that he wanted her to drive to a future instead of to her death, which is what prompts her to quit the gang.
    • Ghost, whose real name is Dan Murasaki, covered his face as he didn't want to rise to the top thanks to being the former leader's brother. Instead, he chose violence as a way of making a name for himself. After Yagami beats him, Seyama is able to reason with Dan to be his own man and mourn his brother in a healthy manner.
    • Then there's Yuma himself. Turns out he was into motorcross in middle school thanks to his father, but after he left for another woman, it became a Trauma Button for his mother and Yuma was forced to study for a good job instead, with her refusing the signs of what he really wants. After Yagami beats Yuma, Yuma admits he joined Made in Heaven because he want to race and can't let it go, so Yagami convinces him he has to stop being what his mother wants to see if he wants to truly be happy. Seyama says his mother is tough nut to crack, so Yagami summons all of Made of Heaven to help her see the truth. Yuma then lays it bare: he joined the disciplinary committee because he could take his frustrations out on people being able to pursue their passions while he can't and how he hated being a perfect student when he had his bike on his mind, begging his mother to stop being ignorant and for once see him for what he is. This finally convinces her to let her son pursue his dreams.

The Kaito Files

  • Kaito's treatment of Jun. Despite the fact that he isn't his biological father, it's rather sweet he quickly warms up to him and doesn't see him as The Load, especially compared to his actual father Kyoya, who flat-out cut him simply for daring to touch his precious knife collection.
  • Bizarrely enough, Fudo, who previously appeared in the main game's Boxing School Story as Kenya's Abusive Parent, gets a moment of nobility here. After being beaten by Kaito, he opts to leave despite still being more than physically able to continue the fight. As he believes Jun's word that Kaito is his father, he decides that he can't go through with tearing a family apart, relating to Kaito how he alienated Kenya by treating him poorly. It seems that Kenya's last punch before cutting all ties with him for good actually knocked a Heel Realization into him.
  • While staking out Kenmochi, Kaito decides to light a cigarette to pass the time. When it turns out that Jun happens to smoke the same brand of cigarettes as him, he swipes the cigarette from Jun and tells him off for smoking at his age. In this one scene alone, Kaito has already proven to be a far better father figure to the boy than Kyoya could ever hope to be.
  • The Final Boss in its entirety. Compared to facing down scheming Chessmasters like Shibusawa or Monsters like Iwami, Kaito's story doesn't end with him taking down Sadamoto, but rather fighting for his honor with someone of pure heart like Shirakaba, who also has feelings for Mikiko and shares his desire of wanting to see her happy.
    • And when Kaito wins the duel fair and square, Shirakaba ultimately steps aside and leaves Mikiko with Kaito - leading to the Yakuza franchise's first genuine Happy Ending. And given everything Kaito and Mikiko have gone through, it's very well-deserved.
    • Tellingly, the song that plays in their final bout isn't an intense and hype-inducing one like "Two Dragons" or a somber and tragic one like "Unwavering Belief", but rather the gentle and wistful "Duel", which is in fact a rearrangement of the base game's end credits theme, "Not Alone".
    • Oddly enough, considering Kaito is Judgment's equivalent of Kiryu, and the objective telling the player to defend [Kaito's] honor with [his] fists, it calls to mind what Kuze said to Kiryu during their final bout in Yakuza 0.
      Kuze: As long as a man has pride, he can die with a smile on his face.

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