[1] Obolensky's parents were Prince Platon Sergeyevich Obolensky-Neledinsky-Meletzky (1850–1913)[2] and Maria Konstantinovna Naryshkina (1861–1929).

He was a lieutenant colonel in the U.S. paratroopers and a member of the Office of Strategic Services (OSS), forerunner of the CIA, and made his first five jumps in 1943 at the age of 53.

Tarsaidze later wrote a novel about the parents of Obolensky's first wife, Alexander II and Catherine Dolgorukov.

[7] In 1949, he started his own public relations firm in New York City, Serge Obolensky Associates, Inc.,[6] handling accounts like Piper-Heidsieck champagne.

Princess Sylvia Sergeievna Obolensky (1931–1997),[14] was Ava's daughter with Raimund von Hofmannsthal.

Sylvia married Jean-Louis Ganshof van der Meersch (1924–1982) in New York City on November 1, 1950,[17] they divorced in 1957 without issue.

On June 3, 1971, he married for the third and final time to Marilyn Fraser-Wall (1929–2007) of Grosse Pointe Farms, Michigan, with whom he did not have children.