PokéBase - Pokémon Q&A
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Obviously, Meowth of Team Rocket and even Copycat's Dudou (and let's not forget Chatot!) proved that Pokémon are capable of speaking. But are they capable of understanding the human language? Meowth seems to be the only Pokémon so far that actually understands what it's saying.

That's what I'm wondering. Could there be a time where all Pokémon learn to talk, and above that, understand what they're saying? If you taught a few to speak, would they teach others around them and their offspring until it continues to the point where you can step out of your house and a Pidgey says 'hey, how's it going?' in sort of an evolution?

An example specifying Staka's claim would be Latios and Latias.

And yes, from an anime standpoint, they can clearly understand it, though they don't speak it, usually.
Do you think they would speak only the language of the The region they are from? If so, what would Magikarps speak, seeing they are everywhere...
Pokémon understand their trainers, and other people. But, all Pokémon can talk to their trainers if they are bonded. Just like in the Detective Pikachu game/movie, Pikachu can talk, but that's because Tim is very close to the Pikachu.

Spoiler about the movie: an even when they just met, in the movie the Pikachu was Tim's father.
Yo. That is a big spoiler. Also, I am unsure if all Pokémon can understand their trainer if bonded enough. I spent 3 years with this Gyarados and it still won’t obey my orders.
That's a game mechanic. You as the character are still 10/11. Forever.

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I wouldn't think so. Pokemon are like animals, and animals do not carry the same type of intelligence that humans do. There's a reason animals are not called "intelligent life" like humans are - their forms of cognition are different, and I believe that this difference would render a talking Pokemon teaching these things to another Pokemon unlikely to be feasible.

If this answer isn't good enough or doesn't answer your question, I don't know if there is one suitable enough.

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There was a gorilla that can do sign language and understand humans.
Also animals can understand your basic words and body language if you train them. Guess what else you train? Pokémon!
The Pokémon franchise often expresses Pokémon as just as intelligent, if not more, than Humans. There are loads of times Pokémon are seen doing tasks unaided that intelligent life is incapable of. Also, Alakazam exists. :P

I think there is just a language barrier that only few can break- like how Ash somehow seems to understand Pikachu... kind of like how The Guardians of the Galaxy understand Groot. :P
I. Am. Groot.
Ash isn't always able to understand what Pikachu is saying, iirc.

Yes, gorillas can communicate back with humans, but the question was, if i'm interpreting it correctly, if that communication could be passed on by the gorilla to another, for instance. I don't know if that's possible. I'm not thinking that it's impossible for humans to teach Pokémon to do this, but my (I believe) educated conjecture would lean away from Pokémon further teaching it down the chain, if you get what I'm saying.
Staka, there are a select few outliers. Alakazam, Metagross, Beeheyem, and generally a lot of Psychic types are ones that come to mind, but I'm postulating this as a rule of thumb. Psychic and ghost types, I think, are a different story. (good example would be the Gen 2 movie Slowking)
N is able to understand Pokémon and have intelligent conversations. The Pokémon mystery dungeons series, while not being "canon", intelligent Pokémon. Pokémon anime episode portray Ash's (and other trainer's) Pokémon as having their own conscious thoughts and conversations when not listening to their trainer (also, they are able to understand move names pretty intelligently, for some reason). I'm not saying every Pokémon can learn a human dialect, but most, if not all Pokémon are intelligent lifeforms. :P
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Like in Pokémon anime terms, the solution would be Arceus or Mewtwo giving all Pokémon the power of speech. Even unknown and magnemites could probably use sign language. I don’t know if all Pokémon can learn to speak, some Pokémon probably wouldn’t want to speak.

It seems like legendary Pokémon can speak, either with their mouths or telepathically.

So theoretically in the Pokémon world, some, most of even all Pokémon could speak.
(Basically if the same way humans could fly if god said “let all humans fly”, it’s just Arceus being “let all Pokémon speak”).

Mewtwo, Latios, Arceus, Latias Bill(from Pokémon blue, as a Pokémon), Chatot, Darkrai(using Illusions), Zoroark(Also illusions), Gastly and Hunter, Lapras, Hoopa and countless other Pokémon learn to speak. I don’t see why any Pokémon can’t learn some form of communication.