When Alakshmi takes Allie's father into the Darkness Realm. Allie cries, and when there, Artie starts to go insane when finding Piper note really Megaria .
The complete abuse from Alexander towards Carny. Even Ray feels sorry, and Tatsurion is pissed.
Sasha's being seemingly killed by Saguru removing her heart. Even more heartbreaking when Gabe finds out about it.
Later in the same episode, Saguru's situation after getting his memory back.
Evolved Saguru getting banished into the Creature Realm before Ray's very eyes. He sheds tears at this.
Also, the fact that Ray has to keep this a secret from his family, who are all hoping that Ken is still alive.
Ray finds Alakshmi on one of the Volcano Ships, losing hope of being free and giving up. Ray gives her an emotional speech to lift her spirits, but he gets taken away by the Fire Creatures with Tatsurion, leaving her in a very depressed and saddened state.
Alakshmi: For a moment there, I almost believed you.
When Ray and his friends go to the Water Civilization, they meet up with Ray's father. Ray starts talking about how much fun he will have when Ken returns, but he cannot.
The next episode, where Artie is so relieved to see Piper again that he gets abusive and careless towards Allie.
Made even worse when she tells her dad that Piper's gone, and not coming back.
Artie: I... suppose it was too good to be true.
Allie's influence from the Cloak of Dark Illusions has made her so dangerous that she runs away from her friends, and when she sees Ray with Squeaky, as well as Megaria being a conscious, she loses control. She even rants on Ray about proving that she is too dangerous.
Allie: Do you want me to destroy you?! Do you want to be sucked into this stupid cloak?!
Ray's pat on the back makes it even more heartbreaking.
"Deluge" finally reveals Ken to his family again. Though by then, he's a barely human beast, who can barely contain himself anymore.
For most of "Fallout", Tatsurion is sure that his family is dead.
Ray having to leave his family to deal wit the crisis of the episode.
The sheer devastation of water's attack.
The episode "The Siphon" reveals The five Beast Kings WILLINGLY gave their power to the original masters to power the veil for the sake of both worlds, but for some unknown reason, the masters backstabbed them, buried them alive, and created a myth portraying them as Eldritch Abominations that exists to the present day. Ray seemed saddened and confused, Master Chavez looked completely horrified.