In 1946 Czesław Miłosz started his diplomatic service in the USA, which allowed him a more serious encounter with American culture, particularly with American poetry. He would observe it closely and participate in it till the end of his life. This article discusses the cultural shock experienced by Miłosz, who arrived in safe and affluent America from a Europe devastated by the war. It also talks about the poet’s distance towards American culture and about his interest, sometimes bordering on ambiguous fascination, in such authors as Walt Whitman or Robinson Jeffers. In the 1960s and 70s, as a resident of California, Miłosz argued with contemporary American poetry, Robert Lowell and Allen Ginsberg among others. His argument focused on two fundamental issues: poets’ concentration on their own experiences or their need to capture the greatest possible part of the world external to them and different understandings of nihilism. Frequently accusing confessional poets of feeling sorry for themselves, of dazzling readers with their own “I”, only towards the end of his life did Miłosz start to reveal, in such poems as This or To Allen Ginsberg, his own doubts and despairs that he had kept secret for private reasons and as part of his artistic strategy