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No, Ash did not show feelings of being upset once May announced that she wanted to leave in order to travel in the Johto region in order to compete in the Pokémon Contests that were held in the Johto region. Ash likely felt some disappointment but he was likely feeling proud for May's decision to decide to travel all by herself in the Johto region in order to compete in the Pokémon Contests there.

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Q: Did ash from Pokemon get upset when may lefy?
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