Even the toughest Street Urchins will cry when they see their dead sibling again only for it to be a mere illusion.
- In the second Kingdom, it becomes clear that the world of the Kingdoms is likely part of Toshiro's mind, like some kind of Palace. In an optional hideout talk, Erina has a brief existential crisis, as she now has reason to believe she might literally be a figment of Toshiro's imagination. The rest of the party reassures her, but it later comes to full-blown fruititon as Erina was revealed to be a Persona taking Natsuhara's form.
- It's nowhere near as grim as some of the examples that occurred in the series, but Natsuhara's fall easily counts. After Toshiro and Natsuhara expose Nakabachi and subject him to justice, a lynch mob formed against the Evil Teacher and drove him to insanity. As they're discussing him in a train station one night, the unbelievable happened. An insane and obviously wrong Nakabachi absentmindedly tried to throw Natsuhara onto an incoming train as revenge only for her to slip off the train tracks and get ran over by an incoming train. It's heartbreaking when we find out the once-confident and upfront girl ends up despondent and gravely injured, but the worst is Toshiro's response to the fallout. He believed that Nakabachi got the last laugh and blames himself for ruining Natsuhara's life despite it being an accident that nobody really saw coming; even Nakabachi had done this in a delirious haze rather than specifically to get revenge, as neither Toshiro nor Natsuhara could have predicted the other students would break him that badly. The only thing that holds this back from being as bad as say, Kasumi being ran over and killed instantly or Hikari being driven to near-catatonia by an ultra-realistic Trauma Conga Line is the fact that Natsuhara is still alive and doesn't remain depressed for very long, although she's crippled for life and can no longer live as a normal girl.
- The post-credits scene where we find out Natsuhara is still alive is this mixed with heartwarming. Despite being gravely crippled and no longer having a shot at a normal life, she still manages to live optimistically all the way to adulthood, and approaches Toshiro to rekindle their relationship as he is no longer under the bounds of his arranged ex-fiancee and his father.
- Toshiro's mother was a fatally ill woman, and his father's strict discipline prevented Toshiro from seeing her when her illness got worse (though, she was far kinder than his father ever was). In a moment of rebellion, a young Toshiro took his mother out to a park on the top of a convenience store. Initially, the two were incredibly happy to share this rare moment of joy, but then Yuki collapsed (and died not long after). This resulted in Toshiro blaming himself for his mother's death, even though he was a child at the time who just wanted to see his mother again. Not only did his father become even stricter after that, but he contributed in further blaming Toshiro for his mother's death. And he still felt that guilt into adulthood.
- Toshiro's Giver of Lame Names running gag suddenly becomes Harsher in Hindsight when we find out he got it from her.
- Gets worse when he finally remembers this during Yoshiki's kingdom. Upon entering an area that takes the form of an amusement park, he's confronted with a disembodied voice that, considering the kingdoms are based on Toshiro's own cognition, representative of his own guilt (it torments him by saying that it's all his fault and that he killed his mother and so on). This causes him to Freak Out and start screaming and begging for forgiveness. He gets over it quickly, but it clearly seems to affect him.
- Not aided by the fact that the cognitive Yoshiki ends up killing a cognitive Yuki (in an attempt to kill Toshiro, the cognitive Yuki pushed him out of the way and took the blow herself) before disappearing. Toshiro still feels guilty for what happened and sounds on the verge of tears. Yuki assures him that it was never his fault and that she never resented him for it either (something he also worried about), along with saying that she loved him. And then we're treated with a flashback of a younger Toshiro and the real Yuki happy in Yuki's final moments, proving it was never a mistake. And then the cognitive Yuki disappears. Which is enough to bring Toshiro to tears. Ouch.
- It's clear the events of this whole arc resonate with Futaba, as she's watching Toshiro go through something very similar to what she did (though for better or for worse, there was no utterly depraved maniac to blame for his mom's death unlike Futaba — the whole thing is a mere mishap that just happened). While she's grown enough over the events of Persona 5 to help Toshiro through this, there are times you can tell she's putting on a brave face.
- Yusuke, as well, takes the revelation of Toshiro's Missing Mom hard - although he, like Futaba, is adamant that Yuki loved Toshiro because he has proof of a mother's love in the form of the Sayuri painting, he solemnly notes that he never actually knew his mom - so he can only speculate.
- Speaking of Toshiro's father, he was already strict from the start but became even worse after Yuki's death to the point of being emotionally and physically abusive to Toshiro. From mentions of him enabling his son's thoughts that he caused his mother's death (despite it not being his fault), to resorting to corporal punishment if Toshiro didn't follow his orders, to strictly controlling his every interaction, it's not hard to feel terrible for Toshiro for what Yoshiki put him through, especially if you have overbearing and controlling parents who legitimately believes their oppressive actions are for your own good, something that happens a lot in real life. After the downfall of Shido, Yoshiki further controlled Toshiro and rigged elections (using his shady connections) to get Toshiro the spot of Prime Minister, along with forcing him into an Arranged Marriage, but Toshiro was too scared to rebel against by that point considering the last time he tried to overturn a corrupt authority figure, it got many people hurt and/or arrested, lest be said figure being his father who heavily influenced his life since childhood rather than a random corrupt teacher who just happened to lay his dirty hands on his school.
- Guernica's backstory. Once an orphan named Tao who lived alongside her sister Luca, they were thrown away by their parents and forced to live on the streets as orphans. As horrible as the lives of some of the characters are, at least they aren't scraping at the streets. On the other hand, Tao and Luca had to salvage scraps and fight with rats for food. Then Luca died to starvation and Tao rechristened herself as "Guernica" and resorted to vandalizing public buildings as revenge against society, only to be captured, manipulated and brainwashed by some god who didn't care about her by the slightest bit other than as a weapon to be unleashed into the real world to eradicate humanity. When Guernica breaks out of her programming by "Luca's" encouraging words, she just breaks into tears as she finds out the sister she's "reuniting" with is nothing but an illusion. Getting to see your lost beloved sibling, the only person who cared about you only for them to reveal themselves to be an ephemeral clone is heartbreaking, and is enough to put even the most hardened street punks like Guernica into tears.
