In The Lord of the Rings and other writings, J. R. R. Tolkien creates enchantment for the reader while at the same moment he puts enchantment at risk for loss. Tolkien never resolves whether enchantment or loss “wins,” instead leaving them in a dialogue. This interplay between enchantment and loss symbolizes the need to maintain metaphorical enchantment (connection, meaning) while confronted by loss. One reason many adolescents are absorbed by Tolkien and other fantasists is that adolescence involves a “normal disenchantment” due to turning from play to increased engagement with adult realities. Tolkien embodied the interplay of enchantment and loss in his life. His writings are an expression of his struggle to maintain enchantment in the face of the many losses he experienced, ranging from his orphaning to the horrors of World War I.