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The ONLY time I actually had a hard time with someone was ten years ago when Fire Red came out, back then I solo'd every game with my starter and that particular run I had chosen Charmander, needless to say, Misty wrecked my fucking shit sideways, not even overleveling helped. I dropped the game and picked it up again weeks later, restarted, picked Squirtle (which ended up being the better choice anyways), got myself some good ass Pokémon and blazed the game with them.