She was educated by governesses in the ancestral home at Minterne Magna in Dorset, along with her three younger siblings, and later attended Downham School.

Her great-great aunt was the nineteenth-century adventurer and courtesan Jane Digby (1807–1881), notorious for her exotic travels and scandalous personal life.

Shortly after giving birth, Pamela and the newborn were photographed by Cecil Beaton for Life magazine, its first cover of a mother with baby.

His letter to Pamela asking her to make good on new gambling debt of $12,000 (equivalent to over $190,000 in 2020[8]) forced her to take a £12-a-week job at the Ministry of Supply and sell her wedding presents and much of her jewellery, while keeping it a secret from her in-laws.

[8] She fell in love and started an affair with American envoy Averell Harriman, who was married and almost 30 years her senior.

When her marriage to Randolph Churchill started to fall apart, she became romantically involved with Averell Harriman, who later became her third husband; Edward R. Murrow; and John Hay "Jock" Whitney.

[10] William S. Paley, briefly a consort during WWII,[citation needed] said: "She is the greatest courtesan of the century", meaning it as a compliment.

"[11] In 1948, Harriman moved to Paris and began a five-year-long romance with Gianni Agnelli, a noted playboy and heir to the Fiat empire, who was a year younger than she was.

By Pamela's account, she nursed him back to health while he was in the hospital, then while he was convalescing in Turin they decided together to end their relationship.

Hayward was rich with income from his productions, notably the very successful The Sound of Music, allowing for a luxurious lifestyle mostly between their residence in New York City and the Westchester County estate "Haywire."

[4] The day after Hayward's funeral, Pamela arranged to resume her acquaintance with her former lover, Harriman, then 79 years old and recently widowed.

[4] Pamela Harriman died on February 5, 1997[15] at the American Hospital, Neuilly-sur-Seine, after suffering a cerebral hemorrhage while swimming at the Paris Ritz one day earlier.

The morning after her death, President Jacques Chirac of France placed the Grand Cross of the Légion d'honneur on her flag-draped coffin.