If you could have a conversation with Ash what would you talk about?

[Master Cyrus]

Ash mah boy- Y U NO USE THUNDERSTONE. Or, why do you neglect palpitoad so much.

 

[John Understands]

Ash, have you ever gone on the Internet and looked up yourself...?

 

[CrystaI]

I'll ask him for a challenge of such:

Go beat Gary Oak, Paul, Barry and Trip in a 6 vs 6 full battle! If you fail such challenge, then you should really consider giving up being a Pokemon Master. Really, do you really think you can become a Pokemon Master, or may be just a League Champion if you lose to them so often? I'm sick and tired of watching you failing all the time, and I really don't understand how you personally can withstand such a long failure without even getting depressing, and more doubtful that you don't even have the thought of trying harder the next time. Other trainers give up long ago if they continue failing over and over......
You don't just "become" a Pokemon Master or League Champion by luck. Those two are something to be "achieve" by efforts!!! If you can't even make the effort to overtake your rivals, then stop your daydreaming. I don't want to continue daydreaming with you for anymore further. You had already daydreamed for 16 years, now show me you had the ability to turn your dream into reality!

 

[Five-Gate Omega]

I'd ask him one simple question: WANNA BATTLE?!!!

If he says yes, I'll take him on with a Cloyster, Exeggutor, Arcanine, Nidoking, Golem, and Porygon2(forget the fact that Porygon and Evos are banned from the show) against whatever six pokemon he has on him. He would most likely lose unless he happens to be carriying nothing but his best pokemon.

 

[Akromatic]

Have you ever heard of Palletshipping?
Do you know basic math?
Do you know anything besides Pokemon?
Do you know what Team Plasma is?
Do you remember your Pidgey?

 

[Paulisthebest]

Do you remember your Pidgey?

For some reason I can't help but feel that Ash would remember that Pidgey that knocked him away with Gust and then Sand-Attack before it flew away. Remember he didn't catch a Pidgey he caught Pidgeotto 2 episodes later though?

Haha, seriously it would not surprise me if he remembered "the one that got away" instead of the Pidgeot he left behind in Viridian Forest all those "years" ago.

 

[J J M]

Whether he actually had already aged and hit puberty a long time ago but is just pretending to hide it so things don't get awkward in the group.