Unmarked spoilers below
- Mokou's backstory is tragic enough, especially when paired with her theme song.
- Nitori Gets Caught In The Flow has its own soulcrushingly painful take on the story of Kaguya and Mokou's feud. Mokou's Father secretly never loved her and tried to make use of her bond to Kaguya to marry the Moon Princess, so Kaguya decided to humiliate him and let Mokou hate her. This fanfic goes even further with the sadness, as a time-displaced Nitori futilely tries to change her destiny after making friends with her. To twist the knife even more, when Nitori returns to present-day Gensokyo, Mokou has somewhat forgotten her after the thousand-or-so intervening years. Luckily, they at least get a happy ending.
- Yuyuko's backstory is just as bawl-worthy. Her ability was, at first, to manipulate spirits of the dead. As time went on, it grew stronger and stronger, to the point of being able to will death onto mortals. Terrified of her ability, she committed suicide, and her body was used to seal off a misfortune-bringing tree, which later led to the events of Perfect Cherry Blossom.
- Parsee Mizuhashi. Jealousy is a very strong emotion, as anyone who has felt it can attest to. Feeling it for a just a short time can bring great pain to the person, and Parsee has to feel it for thousands of years as part of her curse. Imagine how much pain she is in now, and how many times have a person crossing her bridge felt pity for her just for her to shrug it off again and again, out of, well, being jealous of all of them for even showing pity, even if she doesn't even need or have to. And she's stuck with it, forever.
- Koishi Komeiji's backstory is also pretty saddening. Like her sister Satori, she was born with the power to read minds, however she hated the fear it caused people towards her, so she closed her third eye to prevent herself from reading other people's minds. Sadly this included herself, denying her the ability to think, leaving her as an Empty Shell who can only communicate to people through her subconscious. Even worse, unlike her sister, she travels around Gensokyo and whoever looks away from her after seeing her will forget they ever saw her, meaning that she practically doesn't exist except to the people who have prior knowledge of her. And if that wasn't enough, her dialogue after her fight with Reimu and Marisa implies that she is starting to feel regretful.
- Hopeless Masquerade has her actually expressing some emotions and thoughts; however, this is due to her having the Mask of Hope, and when she gives it to Kokoro, it's implied that she will go back to her Empty Shell state. If there is any consolation, Byakuren does mention that by being an Empty Shell, Koishi is close to Enlightenment.
- Junko's backstory, what with possibly having lost her husband to another woman, and then learning that her son was killed by the same man, causing her to become mad with grief and resentment to the point she became a spirit representing her own feelings of anger and sorrow, with no other purpose to existence than to feel an everlasting hatred.
- Looking at Hecatia and who she's based on reveals that she suffered a loss almost as painful and equally scarring from Apollo's death - Hecate is often depicted as an aspect of the moon goddess Artemis. Hecatia lost her twin brother.
- Some music from the series can be sad, too. See "Legend of Hourai", "Soul's Resting Place", and "The Purest Sky and Sea". "The Wheelchair's Future in Space" from Magical Astronomy also ended up qualifying as this.