It would seem when he came to see Locke as a child, he came from his future self then, as his old self was a hippie.

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Lovin' LOST

I have a theory. What if there is more than one Richard? Think about it. When Hallowax was making the Orchid video, the rabbit appeared out of nowhere. So there were two number (15 or 19 I can't remember). If the Orchid video is true, wouldn't sending Richard to the past mean that another Richard will 'pop up' on the island at some point in the near future? Thus sending Richard to different points in time (Black Rock crash, Locke's birth, Juliet's recruitment) would mean another one would pop up on the island. So it may seem like Richard is ageless but in reality he is not. Also, whatever any Richard learns, the others know automatically just like Faraday in 'The Constant'. That's how Ben and the Others know so much about the island.

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When will I learn? The answer to life's problems aren't at the bottom of a bottle, they're on TV!