Im not really type of person which can easily cry,but i have to admit how some moments got me teary like, such as:
When Butterfree was released: It was sad to see Ash parting of with it after having it for so short and Butterfree finding his "love of life" and courage he demonstrated to be with her was admiring and touching to see. Whole goodbye scene was heart breaking in general.
When Arbok and Weezing departed with Team Rocket: They were TR signature pokemon back in day being like part of family. You can tell how much they were attached to Jessie and James having lot of loyalty to their trainers and having them leave after going through so much so much with their partners was very moving. Especially sad scene to which i didn't stayed indifferent was when TR was beat to death by Tyranitar to buy time for their pokemon to escape, and music which played was doleful.
Hopefully we will see them at least once more before anime ends.
When Misty released Togetic: somehow goodbye episodes always seem like saddest ones to me. Whether you liked Togepi or not it was hard to stay indifferent to departure with Misty and Togetic having to split up after so much time they spent together. Their relationship was like mother-son and Misty and baby pokemon clearly showed how attached they became to each other, with lot of care being put into his growth. Whole ending scene when trainer and her partner burst into tears was truly sad, and it showed growth in character coming to understand how regardless of how she may felt its for best to leave him to go with his friends protecting Mirage kingdom.
"Gotta Catch Ya Later"- probably one of most heart moving episodes which pokemon ever had. Whole episode was full of emotions and sad atmosphere which surrounded it, being sad to see Ash, Misty and Brock having to split up after so many adventures they spent together going through both bad and good times, becoming very close and attached to each other as friends. Most touching parts were when Misty was forced to leave her friends and go back to gym being on verge of tears and whole Goodbye song which started to play only added more to momentum. And when Ash burst out in tears when Misty and Brock left him really accented how much their friendship and everything they went through meant to him. I admit i got little teary in this episode.
Coincidentally this happened to be Misty last episode as main character too and it was disappointing to see such a great character leave, because she really knew how to add more life into cast and i felt she had potential to offer much more .
I wish she returns to cast for one more ride tying up loose ends and getting more development, but at this point its a pipe dream sadly.