After losing a ribbon to Harley, May arrives on Chrysanthemum Island, ready to win her third ribbon. Ash is also working hard trying to help Sceptile regain its ability to use Grass-type attacks after breaking its heart. When Drew shows up, May finds out he didn't send her the letter. Later, while training on the beach, she meets a girl named Brianna who reveals that she sent the letter and rose to May. When Brianna finds out May knows Drew, she grows embarrassed as she has a crush on Drew and intended the letter and Rose to be sent to him. When she finally meets Drew, Brianna claims that she will beat May in the contest and win Drew's respect and love! Meanwhile, Jessie also enters the contest with James' Mime Jr.