The 9 Alleged Love Affairs JFK Tried to Keep Secret His Entire Life

The 35th president of the United States, John F. Kennedy, was notorious for being a ladies man. Many speculated his affairs during his presidency, but since his death in 1963, some of his mistresses have revealed just how serious those relationships were.

Here are 9 alleged love affairs JFK tried to keep secret his entire life, including one woman who became pregnant with his child (page 6) and another who was his wife’s own press secretary (page 8).

1. Gunilla von Post

John Fitzgerald Kennedy signing documents in his office.

John F. Kennedy had a few affairs in his time — including one with a woman named Gunilla von Post . | AFP/Stringer/Getty Images

  • He wrote her secret love letters.

JFK’s romantic relationship with Gunilla von Post began before he wed eventual first lady Jackie Kennedy — and continued well into his marriage, too. In 2010, one year before she died, von Post offered up secret love letters from JFK for auction.

According to ABC News, “On June 28, 1954, during the summer after he was married, Kennedy wrote to von Post, saying: ‘I might get a boat and sail around the Mediterranean for two weeks — with you as crew.’”

This wasn’t the first time, however, that von Post spilled about their affair. In a 1997 interview with 20/20, she revealed that at another point following his marriage, she and JFK took a secret getaway to Sweden. “I borrowed him for a week, a beautiful week that no one can take away from me, from that,” she said.

Next: Jackie knew about this affair.

2. Priscilla Wear

Jackie Kennedy wearing dark sunglasses.

Jackie O. was often aware of her husband’s tomcatting. | Evening Standard/Getty Images

  • She was a White House staff member.

Jackie was well-aware of her husband’s affair with White House staff member Priscilla Wear. Barbara Gamarekian, a press aide under the president, recalled a shocking moment when Jackie was speaking to a Paris-Match reporter about Wear.

Mrs. Kennedy said, ‘This is the girl who supposedly is sleeping with my husband,’ and the reporter was utterly taken aback.”

Next: There were conspiracy theories tied to her death.

3. Mary Pinchot Meyer

Mary Pinchot Meyer in a photograph.

Mary Pinchot Meyer had an affair with the former president. | ATInteresting via Twitter

  • She auctioned off a four-page love letter from JFK.

Mary Pinchot Meyer reportedly penned details about her affair with JFK in her diary. It appears the president was doing some writing about their relationship, as well — but directly to Meyer. In 2016, a four-page letter he’d handwritten to Meyer was discovered in Boston’s RR Auction, which read:

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. I know it is unwise, irrational, and that you may hate it — on the other hand you may not — and I will love it. 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.

In October 1964, Meyer was mysteriously shot twice to her death. Although her murder remains unresolved, many have speculated conspiracy theories surrounding her affair with JFK.

Next: She often joined him on official presidential trips.

4. Jill Cowan

Senator John Fitzgerald Kennedy his wife Jacqueline Kennedy photographed near a tree.

JFK and Jackie didn’t have the perfect relationship. | Stringer/AFP/Getty Images

  • She praised JFK for how much he admired Jackie.

Yet another White House employee JFK reportedly got romantic with was Press Office secretary Jill Cowan, who often joined him on official presidential trips. While she’s never openly discussed their relationship, she has praised JFK for how much he admired Jackie.

“[He was] very proud of the fact Mrs. Kennedy had kept a book of all the place settings and pictures of the flowers, the whole sort of personal touches in the White House,” Cowan admitted in a 1965 interview.

Next: This was his most well-known and controversial affair.

5. Marilyn Monroe

Marilyn Monroe in a portrait.

Marilyn Monroe was also believed to have been in an affair with JFK. | Baron/Getty Images

  • She performed a sultry rendition of “Happy Birthday” for the president.

As much as JFK may have tried to keep his affair with Marilyn Monroe a secret, she became his most well-known and controversial extramarital relationship. Many became suspicious after Monroe’s sultry rendition of “Happy Birthday” to the president in 1962 at a Madison Square Garden fundraiser.

According to People, “Journalist Seymour Hersh wrote that the star’s ‘instability posed a constant threat’ to the President before she mysteriously overdosed at age 36 in 1962.”

Next: She became pregnant with his child.

6. Judith Exner

Judith Exner and John F. Kennedy collage.

Judith Exner had worked closely with John F. Kennedy. | Tillmantweets via Twitter

  • Jackie reportedly knew about this affair.

Judith Exner served as a conduit between Kennedy and mobster Sam Giancana, according to People. On top of being one of JFK’s alleged mistresses, she claimed to have become pregnant with his child. However, she admitted to getting an abortion.

She told People in a 1988 interview, “Jackie couldn’t have been more loving, more concerned about my feelings, more considerate, more gentle.”

Liz Smith, a gossip columnist, claims that Jackie knew about Exner’s role in her husband’s life. She was reportedly “unsurprised” and “fascinated” by their relationship.

Next: Their affair was short and sweet.

7. Marlene Dietrich

Marlene Dietrich speaking on a cellphone on a couch.

Marlene Dietrich had a short affair with Kennedy. | Beck/Express/Getty Images

  • She was 20 years older than the president.

JFK had a short, but sweet affair with Marlene Dietrich, a German-American actress. Dietrich, who was 20 years older than the president, reportedly had a romantic encounter at the White House.

According to a reporter who spoke with The New Yorker, Dietrich claimed, “It was all over sweetly and very soon … and then he went to sleep.”

Next: She was Jackie’s own press secretary.

8. Pamela Turnure

Pamela Turnure during a photoshoot.

Pamela Turnure had the affair right under Jackie’s nose. | NotableHistory via Twitter

  • She bore an eerie resemblance to Jackie.

Pamela Turnure was none other than Jackie’s own press secretary. Turnure and JFK had an ongoing relationship from 1961 to 1963, reportedly spending nights together when Jackie was out of town.

According to The New York Post, “Originally the president’s secretary when he was a senator, Turnure got the White House gig thanks to JFK, who lobbied his wife to hire her.” Turnure was just 21 when she began sleeping with the president, and many have noted she bore an eerie resemblance to Jackie.

Next: She wrote about her affair in a memoir.

9. Mimi Alford

Mimi Alford smiling in a photograph.

Mimi Alford also made the list. | THECOUNTnews via Twitter

  • She found the president “magnetic.”

In 1962, Mimi Alford was an intern at the White House. 50 years later, however, she revealed that she’d been in an 18-month relationship with the president. Alford wrote about her affair in her 2012 memoir, Once Upon a Secret: My Affair with John F. Kennedy and Its Aftermath.

She also opened up about her relationship with JFK to People, admitting that she found the president “magnetic.” However, “he wasn’t looking for a relationship to replace his marriage.”

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