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So Desmond is going through some groundhog day type thing. Charlie is supposed to die and my guess is, so is claire. The old lady that sold him the ring acted like he had been there before. Why she is aware and no one else is is an unknown to me. Perhaps that is how he knew Jack would fix his wife that day they met while running bleachers. Maybe he is the link that can help everyone get off the island, which is a strong enough reason to leave his fiancee. He also knows she will find him and everyone else later on (hence the ending of that one episode where they are on a boat in the arctic). He just can't remember.