Emotional anime moments?

I only have seen two of the movies, and I don't watch the anime anymore.
I really don't "get" why people cry over nonexistent characters. It isn't real.

During Lucario and the Mystery of Mew, (I watched it during the GT with some other PC users) I was one of the people who were complaining that Ash should've been the one who was stuck there instead of Lucario. I:
It was a bit pitiful to see Pikachu sobbing hysterically while watching Ash "die", though haha.

"Go West Young Meowth" really got to me as a kid, watching Meowth try to impress Meowsie by learning to talk and walk on two legs and then him getting rejected by her and beaten down by a Persian was pretty sad. Also James leaving his Chimeco behind.

Whenever any of the main characters released a pokemon. Even Team Rocket grew close to their Pokemon. Like Arbok and Weezing. That episode still makes me sad. Along with Butterfree's goodbye, the episode where James left Chimecho, and the episode when Jessie left Dustox.

Ahhhh, I haven't watched in a looong time, but I do remember beginning to tear up in an episode centered on Max and a ralts. I really wanted him to begin a journey later on with a ralts after that. I actually don't remember what happened or what that episode was about, though. :/

1. good bye buttfree-saddest moment in the anime ever can't deny that
2. good bye pidgeot- envolved into a pidgeot to protect the pidgey the saddest part of all ash never came back for him

the last episode where brock and misty where together and they said there goodbyes saddest moment

For me the most emotional moment will be Pikachu's goodbye and return.

Definitely the moment Pikachu & Ash say goodbye! And not to forget the moment that little cutiepie returns!

The episodes Bye Bye Butterfree and Gotta Catch Ya Later!, definitely. Especially the latter since it had Misty's really emotional song, although I'm not a PokeShipper.

I'm surprised nobody said the Let's Join Hands ending from the Da! arc yet.

I probably cried during Gotta Catch Ya Later! when I was younger.

Also, that moment in the first movie where Ash dies, and all the Pokemon revive him with their tears. Doesn't matter how many times I've seen it, it never gets any better. 8|

After looking up the episode names...

Bye-Bye Butterfree (Ash releases Butterfree)
Charizard's Burning Ambitions (Ash leaves Charizard behind)
Gotta Catch Ya Later (Ash, Brock, and Misty go their separate ways)
Pikachu's Goodbye (Ash releases Pikachu but Pikachu returns to him)

Those are definitely the four saddest. Especially Gotta Catch Ya Later. I remember really feeling Ash's pain when they left each other.

Bye-Bye Butterfree, by far!

I also remember the Ignorance is Blissey episode getting to me to a fair bit, too.

When Latios sacrificed himself in order to save Alto Mare. I think I actually started crying. Granted, I was like 6 or 7 when I saw it. Ahh good times. I've always enjoyed the emotional episodes.

Though it was a movie, that famous scene where Ash turned into stone and all the Pokemon near him were crying... I still find myself going emotional when I see that scene, and I usually don't get emotional over this kind of stuff.