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Tear Jerker: Xiaolin Showdown
Omi coming to the ralization that Raimundo has and has never had a SECRET ELABORATE PLAN.
Omi's Face-Heel Turn in the end of "Judging Omi", and his speech to the other warriors before turning to Chase Young:
"When I tried to lead, none of you would follow; when I tried to talk, none of you would listen. Only one person stood by me, believed in me, and trusted me. That is where I choose to go."
"Return of Pandabubba" when Kimiko's zombiefied dad shuts her down when she tries to talk to him about Pandabubba, telling her harshly to get out and making her cry. Omi's assures afterwards that he doesn't believe her father is really evil and there is something else going on.
"Omi Town", poor Omi.
Omi's disappointment in Jack at the end of the episode "The Apprentice".
During the finale when Good!Chase Young willingly drinks the Lao Meng Long Soup to give the others a chance to escape.
Also during the finale two-parter, Omi having to watch his aged friends die one after another briefly leaves him shocked, such that Dojo has to activate the Sands of Time to save him. Then Omi breaks down crying at what he's just witnessed.
Poor Omi is a magnet for these. In "Crystal Glasses" he thinks that he's going to grow up to be a villain and destroy the temple. Vlad convinces him the only thing to do is take the Long Walk- out into the cold, and never return. Before leaving, Omi looks at a picture of him and the other Chosen Ones.