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My dearest Anne is a poetic war story based around world war two. The young American soldier James (Alexander Ekberg) and his girlfriend Anne (Steinunn Rán Bengtsdóttir) is torn apart due to his enlisting in the 101st Airborne division. The only thing that keeps him going is the letters he sends her, hoping one day they will meet again. But once he lands in the woods of Normandy on the 6th of June 1944 James gets lost and can't find his squad. He must fight the German army alone and afraid with only one thing in his head, getting back home.