During their 10-year marriage, the world was fascinated by John F. Kennedy and Jackie Kennedy‘s marriage. What their connection was like, what they wore and how they acted truly captured audiences for years. But, in addition to all the admiration the world had for their relationship, it seems like their extra-marital affairs received equal or even more attention. And though that was true even more his death in 1963, that became even more the truth after his tragic passing.
In fact, throughout their marriage, both Jackie and Jack were known for jumping back in the dating pool and being unfaithful with one another. From his one-time fling with Hollywood icon Marlene Dietrich, to his rumored affair with Marilyn Monroe to his relationships with White House secretaries, Kennedy’s list of affairs is quite extensive.
If you don’t believe us, check out the list of all of Kennedy’s affairs below.
Mary Pinchot Meyer
Prior to his death in 1963, JFK lived an affair with Mary Pinchot Meyer, the sister-in-law of legendary Washington Post editor Ben Bradlee. Per People, their relationship was revealed when a four-page letter from Kennedy resurfaced in an online auction.
“Why don’t you leave suburbia for once – come and see me – either here – or at the Cape next week or in Boston the 19th,” Kennedy writes in the letter. “I know it is unwise, irrational, and that you may hate it – on the other hand you may not – and I will love it.”
Kennedy continues, “You say that it is good for me not to get what I want. After all of these years – you should give me a more loving answer than that. Why don’t you just say yes.”
A year after Kennedy’s assassination, Pinchot Meyer was also tragically killed in Georgetown, Washington. Her death still remains unresolved.
Kennedy’s most-talked about affair was with the late actress and sex symbol Marilyn Monroe. Although the world assumed they were together after the iconic “Happy birthday” performance, their rumored affair was only confirmed by insiders years later.
According to J. Randy Taraborrelli by Jackie: Public, Private, Secret, Monroe and Kennedy were together romantically for just one weekend in March 1962. “[JFK] thought [Marilyn] was beautiful, but maybe not the smartest girl in the world,” Taraborrelli writes. “He liked her sense of humor and her playfulness.”
Per investigator John Danoff in the docuseries The Mystery of Marilyn Monroe: The Unheard Tapes, uncovered tapes showed proof of their relationship. “There were numerous tapes made on Marilyn and Jack at the beach house in the act of loving making,” Danoff said. “They went into the bedroom where there was another transmitter, which picked up cuddly talk and taking off her clothes, the sex act in the bed.”
According to a report from ABCNews, per journal entries acquired by Kenneth Tynan’s journal entries he submitted to the New Yorker, Kennedy also had a one-time romp with Hollywood icon Marlene Dietrich.
Per the report, JFK allegedly said to Dietrich, “I hope you aren’t in a hurry,” but she was, claiming “2,000 Jews were waiting to give her a plaque at 7 p.m., and it was now 6:30.”
As the story goes via Tynan’s journal entries, JFK responded by saying, “That doesn’t give us much time, does it?”
Dietrich told Tynan that “it was all over sweetly and very soon. And then he went to sleep. I looked at my watch and it was 6:50.” She also recounted that she had to wake him up to guide her back to her car so she could make it to the ceremony. Short and sweet?
In Christopher Andersen’s biography Jack and Jackie: Portrait of an American Marriage, former White House secretary Mary Gallagher revealed JFK also had an affair with Breakfast at Tiffany’s star Audrey Hepburn. “Audrey had this intoxicating laugh – pretty much what you saw on screen – but she also had this very sexy, very naughty side that the public never saw,” Gallagher remembered, per Daily Mail.
“They managed to keep their affair out of the press, and the fact that it was clandestine only made it that much more intense,” she added.
Actress Angie Dickinson also lived a short fling with the former president. Per Andersen’s biography, Dickinson described him as “the killer type, a devastatingly handsome, charming man – the kind of man your mother hoped you wouldn’t marry.”
“It was the most exciting seven minutes of my life,” she said of sex with the former president.
Judith Exner, who served as a conduit between JFK and mobster Sam Giancana, has also been open about her passionate relationship with Kennedy.
“I was crucified because I had had the audacity to have an affair with Jack Kennedy,” she told People in 1988. “I loved him, but no one wanted to believe that he loved me.”
Remembering their times together, Exner recalled their first night together. “It was a wonderful night of lovemaking,” Exner told the outlet. “Jack couldn’t have been more loving, more concerned about my feelings, more considerate, more gentle… It was amazing to me that he could be so relaxed on the eve of the first primary of his presidential campaign, but unbelievably, he didn’t mention New Hampshire once during our entire night together. The next morning, he sent me a dozen red roses with a card that said, ‘Thinking of you…J.’”
Jill Cowan & Priscila Wear
According to a report from the New York Post, Kennedy had affairs with two secretaries in his staff: Jill Cowan and Priscilla Wear.
Cowan and Wear, who were given security nicknames “Fiddle and Faddle,” would reportedly accompany JFK on “business trips” including to Berlin, Rome, Ireland, Costa Rica, Mexico and Nassau, The Atlantic reported. “Neither did much work,” a former Secret Service agent told author Ronald Kessler, per the New York Post.
Out of all of Kennedy’s affairs, Mimi Alford has been the most open about their extra-marital relationship. In her memoir Once Upon a Secret: My Affair with President John F. Kennedy and Its Aftermath, Alford detailed their 18-month relationship.
“In the summer of 1962, nineteen-year-old Mimi Beardsley arrived in Washington, D.C., to begin an internship in the White House press office,” the book’s description reveals. “After just three days on the job, the privileged but sheltered young woman was presented to the President himself. Almost immediately, the two began an affair that would continue for the next eighteen months. Emotionally unprepared to counter the President’s charisma and power, Mimi was also ill-equipped to handle the feelings of isolation that would follow as she fell into the double life of a college student who was also the secret lover of the most powerful man in the world.”
Diana de Vegh
In a 2021 essay in AirMail, Diana de Vegh opened up about her affair with Kennedy when she was 20 years old and a junior in college. After meeting at a benefit, Kennedy and Vegh reportedly met a few times before making their relationship romantic.
“What could I have been thinking?” de Vegh said, adding “I was feeling, in full movie-star-infatuation mode.” “For a Great Man, he was still in the throes of the male mythology of his time: see pretty young woman, have pretty young woman,” she wrote of the president.
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