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Rite this is kinda random but it has been said that libby's past was going to be explored into more but obviously she dead so can't really do a flashback or anything. So may'be the way it will be done is through her husband who she mentions died to desmond when they meet in that cafe. May'be he was on the Island or something or used to be on the Island, may explain why he had a boat etc. Could also link to why she was a bit nutty i dunno