In the first episode of season 6.
the second episode.
4
In the episode ''Get the Show on the Road'' season 6.
The first one
ash meets dawn in Pokemon platinum.Pokemon pearl and the Pokemon diamond series
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."
i think they first meet in the episode called 'now that's flower power' ;D yeah flower power is that episode you can watch it on youtube.
Episode 30
Ash has never kissed May in any Pokémon episode. There's a rumor that he kissed her in a banned episode, but it was false.
May first appears in Pokemon Advanced Generation. She meets Ash through the course of this series and serves as his traveling companion.
Ash leaves May on the last Hoenn tv episode where Ash heads off to Sinnoh with Pikachu and Aipom