A deep and lifelong friendship existed between Hugo von Hofmannsthal and Carl J. Burckhardt. It began in Vienna in 1918, lasted until Hofmannsthal’s death in 1929 and is documented by a literarily and psychologically prolific exchange of letters. Research on this intensive male relationship has long been surprised by the large age difference between the two friends, which was almost 18 years, and which apparently never played a role. The present essay is an attempt to find reasons for the intensity and cultural fruitfulness of this strange bond.