Ash and May are characters in the Pokémon anime series. Ash meets May in the Sinnoh region in the 541st episode.
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Yes, May returns during the Sinnoh season for the Wallace Cup competition where she meets up with Ash and Brock again.
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Ash meets May in the episodes that take place in the Sinnoh season during the dubbed season of Pokémon Diamond and Pearl: Battle Dimension. The episode in which Ash and May reunite is the episode that is titled "A Full Course Tag Battle" however she first appears near the end of the episode that is titled "Our Cup Runneth Over." May returns in order to participate in the Wallace Cup which takes place in the episodes that are titled "Staging a Heroes' Welcome" and "Pruning a Passel of Pals."