As many awesome moments as there are, there are also just as many heartbreaking moments.
- In its own way, the downfall of Dr. Peachbody. Once a dangerous villain, he's forced to fuse with first his pet boy Benji, thrust into the ancient past, and then fused with Dreadwing, who promptly takes full control of the fused body. By the time Peachbody had encountered Dreadwing, Benji's personality has seemingly died, leaving only a lonely, mad Dr. Peachbody who doesn't seem to realize that Benji is gone. The shredded remnants of Peachbody's soul are eventually forced out of his body, left adrift on the astral plane. By the time Gina encounters him again to finish him off, it's more of a Mercy Kill...
- Ayane's entire life. She's a warm, friendly, loving individual who adores cute things and desperately wants to be a Friend to All Children. However her eyes are so scary and evil that even many of her closest friends can't look her in the eye without being frightened, to say nothing of how children react to them. She's managed to form friendships over the years, and there are some characters (like Brittany) who can look her in the eyes without ill effect, but she also has no memory of her family. In addition, she did have a brief moment of happiness, love, and respect when the Prince of a kingdom of evil Oompa Loompa expies kidnapped her and made her his queen. When her general friendliness started to actually reform the Prince and his people, the Prince's witch sent Ayane back and mindwiped everyone, Ayane included.
- Tirant was the child of superheroes, but after his parents died when fighting with him to stop an evil Mad Scientist who took For Science! to its logical extremes, and noticed how his family members had all dies young, he snapped and decided to become a villain after believing that everyone expected him to make a Heroic Sacrifice as well. But then he ends up eventually making one anyways, to save his lover Array, who had just rescued him and another accomplice from an extradimensional prison.
- Array's first conscious moments were of being tortured by Sherisha, who wanted her ability to create "magends", living spells, using her status as a Magitech device to keep the heroes from doing anything to save her. When Tirant broke into the lab and resued her instead of the items he had originally come to steal, she and all the magends/personalities she made fell in love with him. Right after finally recuing him, he made his Heroic Sacrifice, and she was eventually forced into Dreadwing's service in the hopes of bringing him Back From The D Ead.
- One of Gina'd rivals makes a Heroic Sacrifice to stop a Magma Man Elemental Embodiment under Manhattan she accidentally released, rendering them both Taken for Granite. In her Last Testament that Gina finds and reads right as this is happening, she expresses wistful thinking on how she never had someone like Brittany is to Gina to keep her from reading the inscription that had let the Sealed Evil in a Can loose.
- Former dragon queen T'Mat. Brutally raped and tortured by Dreadwing, she's clearly a PTSD-ridden mess who's desire for revenge against Dreadwing causes her to take actions that nearly have tragic results. Her daughter is forced to dethrone her (non-violently) and take over, doing what she can to care for her mother.
- Calandra the werelioness. She hunted Ash deer for the high bounty on them, only to get slapped with a huge fine when she was caught. She found out she got off VERY LIGHTLY, as Ash deer are actually Ashlander infants who were changed to counteract their power incontinence. Calandra is so horrified by what she did that she throws up, and nearly takes a swan dive over the Despair Event Horizon.
- In the Ayane sidestory webcomic, Nin-Nin, Ayane's pet kitten, is afraid of her despite how much he loves her. (He views her as a friendly T-rex.) Ayane wants nothing more than to pet him, but he's too scared to let her near because of her cursed eyes. One day, Nin-Nin bullied by some alleycats and tries to get Ayane to come with him to scare them off. She gets distracted by talking to a friend, and Nin-Nin ends up along against the bullies. Nin-Nin tries to fight, acting fierce while still frightened, and the alleycats seem to falter. A friendly female alleycat saves Nin-Nin and drives them off. But when she turns to look at Nin-Nin, she's overcome with fright and runs off. Nin-Nin, confused looks at himself... and realizes that his claws are long, almost like katanas. As deadly and ferocious looking... as Ayane's eyes... Realizing how Ayane's felt all this time, he powers through his fear of her eyes to snuggle her, Ayane shedding tears of gratitude at finally being able to cuddle her beloved kitten.
- Ryan and Portia commiserating over their failures to find love, though luckily the Ship Tease they get with each other negates it a bit.