The two Pokémon Characters that I most desire to witness interacting are Red and Cynthia. Not because I want to watch them have a battle (though for the record I think they'd be pretty evenly matched) but because of everything else I think would happen.
You see, both Red and Cynthia are highly respected trainers. They're pretty much two of the strongest trainers on the planet. Legends. Bastions of wisdom and valor. Their heroics are well known, and simultaneously mysterious. Pretty much anyone in universe would expect their meetings to be respectful and dignified. Surely these two great trainers are pillars of rationality.
Ding Dong, that's COMPLETELY wrong.
Red and Cynthia SEEM pretty reasonable in context. Red seems completely calm and controlled when compared to his counterparts, the hot-headed Blue and head-in-the-clouds Green. Cynthia SEEMS wise and mysterious because she shows up to provide exposition and leaves. But Red is the guy who decided to live on top of a mountain for months without a jacket just for kicks, and who has only ever spoken ONCE just to mess with someone. Cynthia goes on vacations to everywhere all the time for reasons that are unclear but seem to be related to archeology and summoning deities, and jumped into a wormhole to another dimension with pretty much no context. Both of them are absurdly powerful and as a result their internal sense of danger is completely broken. The horrors of both the heavens and the earth are known to them, and they survived it already. They both just wander around and actively seek out weirder stuff. (And considering their Pokemon continue to accompany them after all this, we can assume the Pokemon are just as nuts as their trainers.)
So my theory is that if Red and Cynthia ever meet, all semblance of having brain cells is rapidly defenestrated. You take your eyes off them for a second and they are already half a continent away. There's an equal chance of them spending the day petting baby pokemon at the daycare as there is them traveling back in time, summoning a God, and killing it. Heroes will weep. The Earth will shake. And neither Red nor Cynthia will be at all aware of what's going on outside their line of sight.
Please let this be a thing.
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Project Venus!Kieran meets his canon self...
Let's just say they are NOT FOND of each other or their hairstyles
I may draw a ref of PVenus!Kieran later! I also changed up the headband a bit
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🌟🏅 PREORDERS ARE OPEN 🏅🌟
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Simple, it depends on being Gen 5 or earlier and Gen 6 and later.
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Meeting of the Minds (They're all Champions in my au)
I'd go a little more into depth but that'd destroy the immersion and surprise for Project Venus.
Also, Kieran DOES NOT want to be there. At all.
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What’s yalls favorite canon vs fanon depiction chat (from Twitter)
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Before Ash Took The Throne
World Champion: Leon
World's Elite Four: Cynthia, Steven, Lance & Diantha
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