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May

May (Left third gen and the battle frontier seasons and Right from when she showed up in Sinnoh)

May was originally sent on her Pokémon Journey by her father, Norman - The Gym Leader of Petalburg City. At the start she wasn't really fond of Pokémon and was just going so that she had a chance to travel. After having her bike trashed by Ash's Pikachu, she decides to tag along with him on her Pokémon Journey. She picks Torchic as her starter Pokémon and continues on. Before long she is joined on her journey by her brother Max, who can sometimes annoy her, she does really care for and look out for. Into her Pokémon Journey, May discovers Pokémon Contests, a way to show off you're Pokémon's talents in ways other than just battling. Captivated by this she decides to train her Pokémon specifically for the contests. Through this passion, she ends up getting several rivals and competing in Grand Festivals across the world. She is a kind person to everyone but sometimes can get a bit carried away and still shows a bit of naivity when it comes to Pokémon.

 Pokémon

For the list of May's Pokémon click here.