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i just finished rewatching "fire+water" in season 2. The scene where hurley and libby do laundry made me suspicious of libby, in the scene hurley asks if he's seen her before. she looked somewhat like her "cover was blown" and quickly came up with a story that hurley stepped on her foot on the plane. and since we knew that she was in santa rosa along with hurley and in the airport with desmond i was thinking prehaps she is like abbadon in the way that he "helps people get to where they need to be". She was keeping an eye on hurley in santa rosa and she gave desmond the boat because she knew it would get him to the island.