- Diaspro's reasons for being a villain: she was raised to be Sky's wife and the actual ruler of Eraklyon while Sky, who is more likable but not as skilled as a ruler, puts his face on the front, and then Bloom came out of nowhere and Sky broke up with Diaspro, leading the Fairy of Jewels to believe that Bloom is a Gold Digger who somehow ensnared Sky and driving her to join Valtor (with plans to doublecross him later) to save Eraklyon from her. What really makes it sad is that not only Diaspro was willing to let bygone be bygones when it came to Bloom's unprovoked attack due to (correctly) guessing she was a hyperprotective friend of Sky who didn't know the actual situation, but her reasoning, from a royal's point of view, is so sound that Stella and Aisha would have reached the same conclusion had they not known Bloom well enough to realize it was true love.
- This comes to a head in Lapidary, where we see what happens when Diaspro actually Activates, and we see exactly what happens when someone like her has her desires stomped on, over and over again. Among other things, she actually ends up killing Bloom once, only to notice Bloom's reaction, actually commits suicide (the effects we see afterwards when that Loop's Sky blows off her funeral and flirts with Bloom in front of Diaspro's grieving parents), and eventually realizes that her true love never loved her back.
- Long after Diaspro got over that, there was a Loop where Sky did love her. She didn't take it well.
- When they start Looping, the Trix explain they had realized they had become monsters during their time with Tritannus... But they felt they had no choice but continue being villains.
- What became inevitable when Flora put Miele in her Subspace Pocket. Even worse, Fand opted not to let Miele get Activated, instead opting to make that version a program for her terminal, meaning that when she died, that was last time Flora got to see that iteration of her. This led her to tears.
- A trip through Jo Jos Bizarre Adventure Diamond Is Unbreakable doesn't really do much for Nabu beyond give him a Stand that he doesn't understand at all... until it turned out that Yoshikage Kira visited Aisha while Nabu was away. Nabu literally went catatonic as a result once he realized what happened.
- Helia's Setsuna Syndrome. What's worse is that he's completely convinced he's doing it for the good of everyone, and isn't happy about what he has to do for it.
- Helia's encounter with Setsuna Meioh. It looked like she was getting through him before he could do anything stupid... And then Michiru and Haruka burst in chasing the giant fire-breathing chicken Naruto had left there as part of the Great Prank War, and between that and Setsuna's attitude to it Helia convinced himself he had to act for the good of everyone.
- The group finding out how Tecnas Pocket exploded. Tecna herself is completely devastated and nearly stopped doing what she loved.
Tear Jerker / The Winx Club Loops