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On the surface, John F. Kennedy and Jackie Bouvier seemed to have the perfect marriage. They were rich, they were attractive – oh, and of course, one of them was the president and the other the First Lady. But behind the closed doors of the White House, there were some secretive, and sometimes unpleasant, things going on.

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20. JFK was with his mistress when Jackie gave birth

John F. Kennedy had a lot of mistresses… a lot. And when his wife gave birth to a stillborn child in 1956, he was reportedly away on a yacht with one of them. Furthermore, he didn’t rush back to be at his wife’s side either. It took the threat of losing public support and all-important votes before the would-be president finally returned home.

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In 2019 singer Carly Simon, a friend of Jackie’s, told NBC News about the incident. She said that though Jackie had been blasé about her husband’s affairs, “I think that some of the things had more effect on her… For instance, his not being there for the birth of a child. For his being off with a mistress while she was in the hospital.”

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19. Jackie didn’t want to be a housewife

Jackie Kennedy lived in an era where women were expected to take a housewife role once they got married. But she didn’t like that idea at all. Indeed, she actually had a job before wedding John F. Kennedy. She worked for the Washington Times-Herald newspaper and covered some major events.

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In 1953 Jackie wrote to a confidante, an Irish priest called Joseph Leonard, and said, “Maybe I’m just dazzled and picture myself in a glittering world of crowned heads and Men of Destiny – and not just a sad little housewife… That world can be very glamorous from the outside – but if you’re in it – and you’re lonely – it could be a Hell.”

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18. Jackie’s mother allegedly got her father drunk before her wedding

Jackie’s parents were Janet Auchincloss and John Bouvier, and they were bitterly divorced. Bouvier, who had the nickname of “Black Jack” was an alcoholic. Janet decided to use that to her advantage when it came to her daughter’s wedding, and according to biographers she got him so drunk beforehand that he couldn’t walk Jackie down the aisle.

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In the end, Black Jack was indeed absent from the Kennedy wedding, and Jackie’s stepdad Hugh Auchincloss walked her down the aisle instead. To cover, Janet told everyone that her ex-husband had the flu. But Jackie knew the truth, and apparently she never really forgave her mother for doing such a thing.

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17. JFK might have been married before Jackie

It’s long been rumored that John F. Kennedy was secretly married to another woman before he wed Jackie. So the story goes, he and a socialite named Durie Malcolm were at a Palm Beach party back in 1947 when they drunkenly decided to get married. Upon learning of this, John’s furious father destroyed all records of it.

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According to investigative reporter Seymour M. Hersh and his 1997 book The Dark Side of Camelot, friend of the Kennedy family Richard Cardinal Cushing of Boston quietly arranged for the marriage to be annulled. And there are apparently declassified FBI files which suggest the same thing: Jackie was JFK’s second wife.

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16. Jackie wasn’t impressed with JFK at first

During a dinner party in May 1952, the young Jackie Bouvier was introduced to John F. Kennedy, who was then a congressman. Their mutual friend Charles Barlett, the host of the party, was determined that they should meet. Apparently, John was awestruck by Jackie immediately, but she would take more time to grow attracted to him.

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The two of them did apparently flirt during the dinner party, and John asked Jackie out for a drink… but she turned him down. And during a later meeting she saw him in a swimsuit and was far from impressed. She wrote of her future husband in her diary, “He has a funny body, skinny with toothpick legs.”

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15. Jackie considered their relationship “atypical”

In January 2020 a piece of Kennedy history was saved from the auction block and given to the John F. Kennedy Foundation: a letter handwritten by Jackie and sent to JFK just after their child Caroline had been born. It provides some insight into what Jackie herself thought about her most unusual marriage.

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At the end of the three-page-long letter, Jackie writes to John, “You are an atypical husband – increasingly so in one way or another every year since we’ve been married – so you mustn’t be surprised to have an atypical wife – Each of us would have been so lonely with the normal kind.”

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14. John F. Kennedy slept with prostitutes

Seymour Hersh’s 1997 book The Dark Side of Camelot goes into a lot of detail about John F. Kennedy’s sexual habits. According to Hersh, the President used the Secret Service to supply him with an endless stream of women. Many of them were prostitutes, and they may have come from shady underground criminal organizations to boot.

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Hersh interviewed a Secret Service agent for his book, and according to them, Kennedy took photographs of the women whom he bedded. Some of the photos also apparently included the president himself – but the participants in the bedroom scenes were often wearing masks. None of the scandalous photos has surfaced thus far.

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13. Jackie didn’t like her wedding dress

Jackie’s mother Janet was the one who took charge of her daughter’s wedding dress. She hired Ann Lowe, an African-American designer, to create it. It was an ivory-colored silk creation with wax flowers on the skirt. Lowe went to great efforts to make it perfect – she even had to start again from scratch when a first dress was ruined in a flood.

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Yet Jackie disliked the dress. She had wanted a simpler one from the start, rather than the one her family chose. She apparently told people that the gown made her chest look flat or, worse, made her look like a lampshade. And when she was asked who designed it, she reportedly said it was by “a colored woman,” rather than giving Lowe’s name.

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12. Jackie’s own sister might have slept with JFK

Jackie Kennedy had a younger sister, Caroline “Lee” Radziwill, and the two women were rivals in many ways. And according to the 2018 book The Fabulous Bouvier Sisters: The Tragic and Glamorous Lives of Jackie and Lee, there may have been a big betrayal involved as well. Allegedly, Lee once had an affair with John F. Kennedy.

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It was Gore Vidal, the writer, who first suggested that Lee had slept with her sister’s husband. The book about the Bouvier sisters notes that there’s every chance he was telling an untruth, but there’s no doubt Jackie and Lee’s relationship was a fraught one. When Jackie died of non-Hodgkin’s lymphoma in 1994, she didn’t leave her sister anything.

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11. Jackie found it hard to communicate

Jackie’s handwritten letter to her husband from 1957, now in possession of the John F. Kennedy Library Foundation, offers a look at how she perceived herself within her marriage. Jackie wrote in the note that she usually sent “stiff letters” because “It is hard for me to communicate – which you do so beautifully.”

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Jackie also wrote to her husband, “I know everyone says married couples should never separate – as you get off the same wavelength – It is true you do – but I think it is usually good when we go away from each other as we both realize so much.” She signed the letter, “All my love, Jackie,” so it seemed she could still communicate where it counted.

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10. Jackie had fears before her wedding

According to letters Jackie sent to her reverend friend Joseph Leonard, she wasn’t completely sold on the idea of marrying John F. Kennedy. In 1952 she wrote that she thought she was in love with him, but later on she said, “He hurt me terribly when he was campaigning and never called up for weeks.”

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In that same letter Jackie wrote on, “I think he was as much in love with me as he could be with anyone, and now maybe he will want to get married because a senator needs a wife, but if he ever does ask me to marry him it will be for rather practical reasons – because his career is this driving thing with him.”

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9. JFK and his father-in-law reportedly shared a lover

Jackie’s father John “Black Jack” Bouvier was allegedly an alcoholic, gambling-addicted hedonist who slept with both men and women. And apparently he didn’t like his daughter’s prospective husband at all when he first met him. Yet as things progressed, they found they had something in common – a love of sex.

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According to the 2014 book Jacqueline Kennedy Onassis: A Life Beyond Her Wildest Dreams, among Black Jack’s lovers was the songwriter Cole Porter. Porter once made the claim that John and Black Jack hired a showgirl one night and shared the same bed with her. No actual evidence of this beyond Porter’s word exists, however.

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8. Jackie was engaged to someone else for a while

John F. Kennedy wasn’t the first major romance for Jackie. Instead, it was a stockbroker named John Husted. They became engaged in 1952, and Jackie wrote to her friend Joseph Leonard, “I KNOW I will marry this boy. I don’t have to think and wonder – as I always have before – if they are the right one.” But he wasn’t.

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The engagement was announced – in the New York Times no less – in January 1952. But by March the whole thing had been called off. Jackie wrote to Leonard, “I’m ashamed that we both went into it so quickly and gaily, but I think the suffering it brought us both for a while afterwards was the best thing – we both need something of a shock to make us grow up.”

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7. Jackie reportedly confronted Marilyn Monroe

Rumors about JFK and beautiful actress Marilyn Monroe circulated for so long that Jackie eventually decided to take matters into her own hands – allegedly, at least. According to the 2013 book These Few Precious Days: The Final Year of Jack with Jackie by Christopher Andersen, Jackie had a full-on confrontation with the woman she saw as a threat.

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Andersen claimed that Monroe once called Jackie on the phone and told her all about the affair. Jackie could have gotten angry, but instead said drily, “Marilyn, you’ll marry Jack. That’s great. And you’ll move into the White House, and you’ll assume the responsibilities of First Lady, and I’ll move out and you’ll have all the problems.”

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6. Jackie refused to take off the clothes stained with her husband’s blood

As the whole world knows, President Kennedy was shot and killed by an assassin on November 22, 1963. Jackie witnessed the whole thing, which of course must have been unfathomably traumatizing. She was sitting next to her husband when the bullet pierced his skull, and her pink suit was covered in his blood.

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Jackie cleaned her face but refused to take the suit off as she was brought aboard Air Force One. She stood in it, the stains very much visible, as Kennedy’s vice-president Lyndon B. Johnson was sworn in as the new president. Later she claimed she regretted washing the blood off her face, because she wanted everyone to see what had happened.

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5. Jackie didn’t care much about her husband’s affairs

John F. Kennedy slept with a great many women who weren’t his wife, yet Jackie maintained a poker face throughout it all. Why? In 2016 a “close family friend” of the couple told People magazine, “It was a marriage of its time. At the end of the day, Jack came back to Jackie – and that was it. They loved each other.”

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Author Pamela Keough also spoke to People. According to her, Jackie “came from a world where that is what men did, and it was accepted.” And another person who knew the family, Cornelia Guest, said “For these women, if they ever did discuss [their husbands’ infidelities], it was more like, ‘This is what’s going on; let’s go out and get the kids and get on a horse.’”

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4. JFK reminded Jackie of her dad

Some fascinating tidbits about the Kennedys were uncovered when Jackie’s old letters to Joseph Leonard were found. In one of them, the future First Lady wrote about she feared John F. Kennedy was too much like her dad, who had divorced her mother and sent shockwaves rippling through the whole family.

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Jackie wrote of John, “He’s like my father in a way – loves the chase and is bored with the conquest – and once married needs proof he’s still attractive, so flirts with other women and resents you. I saw how that nearly killed Mummy.” And unfortunately, John would indeed prove to be that sort of man.

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3. Jackie had a secretive romance

After her husband’s death Jackie famously married again, to Aristotle Onassis in 1968. However, before that – and not long in fact after JFK was assassinated – she most likely embarked on a romance with David Ormsby-Gore, President Kennedy’s British ambassador to the United States. He had lost his wife in a car crash, and Jackie had of course lost her husband, and their grief drew them together.

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Jackie could have married Ormsby-Gore, but she decided it would be wrong considering that her husband had employed him. In 1968 she wrote a letter to him reading, “If ever I can find some healing and comfort – it has to be with somebody who is not part of all my world of past and pain.”

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2. John F. Kennedy might have been a sex addict

John F. Kennedy might very well have had affairs with women too numerous to count. Among his rumored conquests were Marilyn Monroe, Marlene Dietrich, Anita Ekberg, a gangster’s moll named Judith Exner and White House intern Mimi Alford. These days, experts might well characterize his behavior as sex addiction.

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In 2008 Kennedy biographer Laurence Leamer told ABC News, “When I began my research, I thought all this stuff about JFK’s sex life was exaggerated. But I’m just amazed at how many women there were. He really was a sexual addict.” And allegedly, JFK once informed U.K. Prime Minister Harold Macmillan, “Do you know, Harold, if I don’t have sex every three days, I get a goddamn headache.”

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1. Jackie considered a divorce

The 2014 book Jacqueline Kennedy Onassis: A Life Beyond Her Wildest Dreams lays out the claim that Jackie genuinely considered divorcing JFK at one point. If she had done so, it would have made her the first ever First Lady of the United States to divorce a serving president, and almost certainly caused no end of scandal.

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According to the book’s authors Darwin Porter and Danforth Prince, Jackie had been driven to distraction over the Monroe affair. Her father-in-law offered to pay literally a million dollars for her to remain with John, and it seems she begrudgingly accepted the situation. Since JFK was killed, we’ll never know if the marriage would have lasted the long haul.

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