Jessi-Jo could be a male friend up north where the ice floes are or a guy he travelled with - a guide perhaps on canoe trips....
there isn't a 'she' or 'her' reference in the song...it's always Jessi-Jo.....
at first listen/read it seems like a woman he's talking about, a woman giving him advice, a woman he's needing because he's flyin blind....
BUT the male bonds/friendships on wildnerness adventures and shared experiences that were good and bad, perhaps dangerous, may have him thinking of his buddy, perhaps no longer around, Jessie-Jo...and the warnings he had....
just a thought....
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