As I've mentioned in my post about Pokémon and conventional sports, it is not strange to think that both can go together. Skateboards too belong in that vein of sports, so there is no reason that the two can't go together. Trainers represent the most natural people in the Pokémon world to ride skateboards. Of course, with the recent developments in Alola, it might seem apt to think that some Team Skull members are riders of skateboards. Even so, the most hippie of Trainers might have a penchant for this equipment. One of them is not exactly that, but nonetheless is very familiar.
That Trainer is Ash. In the Johto saga episode for which its English title is "Extreme Pokémon", he divulged that he had some boarding experiences on the grassy hills near Pallet Town. It is this experience that led him to win a sled-skateboarding challenge in the very same episode with Bayleef. I think this is nothing short of impressive and admirable. Though I can't ride a skateboard, I'm interested in owning one and learning how to ride it because of this. It would seem like I'm getting to know his character more.
As for skateboards themselves, I don't mind riding any old plain skateboard. But based on the above, it would be thrilling to have and ride a Pokémon skateboard. I can already think up of possible Pokémon that could be on one. Pikachu is a given, of course, but some of the more down-to-earth Pokémon could be put on a skateboard. Treecko could be one of them, as could be Chimchar and Totodile, for example, to round up the starters. It could very well be exciting to ride a skateboard with motifs of these Pokémon.
Skateboarding tends toward the extreme side of conventional sports, but it is one nevertheless and therefore could still be complemented with Pokémon. There's already a precedent for it in the anime with Ash riding a skateboard, and to have a skateboard decorated with Pokémon is an intriguing prospect. All these connections are seemingly affirmative that skateboarding belongs in the world of Pokémon as any other conventional sport, enough to make me want to ride one right now and realize a "Pokéskateboard" fantasy.
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