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I think May and Ash would do well together. Except she already has a boyfriend maybe in Drew? But I like May better then Misty and Dawn, but I like Misty better then Dawn. But Dawn is still cool a little weak in character lines though. May just seemed cooler and used more variety of Pokemon, she really showed character growth throughout the show.
May and Ash together look like to small kids playing Snakes and Ladder
Misty FTW...There had been many references in the Anime that Misty was in love with Ash...In one episode when Ash gave Misty her bike back she was still sad that she had to leave Ash...They both are passionate for each other lol
Obviously Misty, she and ash were just natural. May was a bit too far out for ash, and Dawn is... Way to young. Ash is a good 5 year older than Dawn by the time that Ash makes it to Dawn. Dawn is 10, Ash is 15.