First off I would like to welcome qrpo. I hope u enjoy your stay and don't worry about the english :)
Secondly EmperorEmpoleon, I think many of us would like to see what you will be able to come up with. Finally I have to agree that the emergence of many of these new members is both awesome and a good thing.
Now for the topic:
I like both episodes AG020 and AG042 because to me it looks that May goes out of her way to try and flirt with Ash. As for when Ash flirts with May I don't think there is one where does or at least tries but I haven't seen the show in some time so I am not really sure.