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1) Ash's battle vs Korrina's newly mega evolved Lucario - whoa, the expressions here were really good
2) Ash's battle against Kukui, the entire thing was so amazing
3) That scene with Mallow and her mom in SM108. I've never cried so much for a series episode and it has really stuck with me since.
There are probably so many more scenes I like but these three are easily the top.
I like the moment when Dawn screams at the balcony. She had a lot of emotions and finally let them out.
The Winding Woods episode was great. We rarely get to see Ash doubt himself.
The summer festival when Misty shows up in a yukata and when Ash comes back to life were my favorite Pokeshippy moments. May and Ash swimming in the sea with the Luvdisc and when he grabs her shoulders after missing the ferry are also good moments. Amourshipping is cute too but it didn't have these kinds of intense moments which was a little sad. The kiss scene is cute but the fact that she didn't confess first or got any hints in her cameo episode will always bother me.
The arc with Chimchar was great. Both the final battle and the moment when it bit Ash.
A really underrated Brock moment is when he stood outside of Charmander's hospital room. That moment really established Brock as the reliable friend/adult.
Not the biggest Iris fan but I love her backstory and the moment when she cried after being defeated by Cynthia who she looked up to was a powerful moment.
Hunter J's death was pretty epic. A fitting ending for a serious villain. Cyrus disappearing was also intense. The admins trying to rescue him but being forced to accept his death (?) in the Amazon special was also interesting.
The entire Birth of Mewtwo special is also great. It's even better if you listened to the CD drama first.