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I know that back in the Sinnoh games, there was a story told that in the past, people and Pokemon used to get married, so it's not like it hasn't happened before. I could never see myself dating a Pokemon though- just seems a bit weird to me.
No, even if it looks human, it is still technically bestiality as all Pokémon are animals, and that is against the law. If Pokémon's suppose to be based off of the real world, then it must apply real world rules.