JFK and Marilyn Monroe… and Audrey Hepburn… and Marlene Dietrich. While his marriage to Jacqueline Bouvier may have been an American fairytale, the 35th President of the United States – whose term in office was tragically cut short by an assassin’s bullet on November 22, 1963 – was a dashing, charismatic figure who enjoyed a long list of affairs and encounters including a host of famous women during his remarkable lifetime.
All the President’s women are said to have included an extraordinary roll call of characters, some of whom would have outraged the public consciousness had they been exposed: mobster’s wife Judith Exner, hostess Ellen Rometsch, the wife of a CIA agent and even an alleged Nazi spy. Lusty Jack had dalliances closer to home, too, allegedly bedding White House intern Mimi Alford as well as a pair of secretaries colourfully dubbed Fiddle and Faddle by the Secret Service.
But his truly eye-opening romances were with some of the most beautiful and alluring stars ever to grace cinema screens. They loved his charm, political leadership and high office; he loved the company of famous faces and reputedly could barely control himself in their presence. From Marilyn Monroe to Angie Dickinson, very few were immune to the Kennedy charm …

JFK and Marilyn Monroe
“Happy birthday, Mister President.”
JFK’s most well-known alleged mistress, Marilyn, famously pouted these words on stage in May 1962. They had met three months earlier in New York, and the spark between the statesman and the sex symbol was immediate. It seems the relationship was consummated at Bing Crosby’s house in Palm Springs, California, and lasted just weeks or even days.
Marilyn was enamoured of Jack, said Tony Oppedisano, friend of Frank Sinatra: “She respected him; she admired him. She loved what he was doing with the country.”
Some sources insist Marilyn was besotted with the President, and even wrote to Jackie to threaten to steal him away and become First Lady. (Jackie already knew about Marilyn, but was more worried that if news got out, his trysts with Mob-affiliated Judith Exner might also leak.) However, Tony believes Marilyn wouldn’t have done that.
“She wasn’t about to break up his marriage. She would not let it go that far, even if she felt that deeply.”
It’s reported that Marilyn had a later affair with JFK’s brother Bobby. “She felt taken advantage of,” says Tony. This led to wild stories of her August 1962 suicide being a Kennedy-organised murder.

Gene Tierney
One of Jack’s earliest A-list romances was with stunning Gene, who hit the big time in Laura (1944). The actress wrote in her autobiography Self Portrait (1978) about meeting the future President in 1946, on the set of Dragonwyck. She was married to designer Oleg Cassini, though they were about to divorce; Jack, yet to enter politics, looked dashing in his Navy uniform.
“I found myself staring into what I thought were the most perfect blue eyes I had ever seen on a man,” she said. “Literally, my heart skipped … When the scene was over, I stepped forward to meet the man whose blue eyes had engaged mine, and whose name turned out to be Jack Kennedy.”
The pair met a second time at the home of skater Sonja Henie, talking and dancing, and were soon lighting up the New York scene. However, Gene’s family disapproved of JFK’s Catholicism and political aspirations, and things fizzled when he went to Congress. The actress visited him in DC, but it wasn’t to be.
“I didn’t think dating an actress, at that point, would be very good for his career,” she mused. “I am not sure I [can] explain … Jack’s charm, but he took life just as it came.”

Lee Remick
Lee was just 22 when she had a fling with JFK – 18 years her senior and a married man – in the late 1950s. However she and her husband, director Bill Colleran, remained friends with the Kennedys and visited the White House in Lee’s capacity as a spokesperson for the Democratic Party.
It was no surprise that she had caught JFK’s eye – she was, says Christopher Andersen, author of the book Jack and Jackie, Portrait of an American Marriage, “drop dead gorgeous” and “the epitome of class and intelligence”. The star would earn an Oscar nomination for Days of Wine and Roses (1962), and also follow in Marilyn’s footsteps and hook up with Jack’s brother Bobby. The pair are said to have spent a number of romantic weekends away together.

Blaze Starr
Saucy Blaze liked her men to be political – she was famous for her illicit affair with long-time Louisiana governor Earl Kemp Long. Known as “The Hottest Blaze in Burlesque”, the voluptuous redhead met then-senator and future commander-in-chief Jack when he visited her strip club in Maryland in 1954. She even scored an invitation to the White House in 1962, amid the Cuban missile crisis.
The star went on to make a couple of screen appearances, both as an actress and playing herself, and decades later she shared that her encounter with the President had been “very quick and very wild”. He “knew exactly what he was doin’ with the girls, so it didn’t take him long,” she explained. It could almost be called a brief Blaze of glory, in fact.

Marlene Dietrich
Formidable Marlene slept with the President in 1962, while he was occupying the highest office in the land. However, it was not a prolonged encounter.
“I don’t remember most of what happened because it was all so quick,” she would later confess. She had actually conducted a lengthy affair with JFK’s father, Joseph P. Kennedy, so in this case it was very much like father, like son. It’s on record that Jack made a “clumsy pass” at the actress in a White House bedroom, prompting her to confide to him, “Mr President, I’m not very young.”
She was 60, in fact. He was not deterred, so Marlene acquiesced to the Presidential ardour, simply requesting of him, “Don’t muss my hair – I’m performing.”

Audrey Hepburn
Gorgeous Audrey was involved with Jack in the days before Jackie, when he had just been elected to the Senate and she was in Oscar contention for her breakthrough role in Roman Holiday (1953). A secretary relayed to Christopher Andersen details of her visits to the senator on Capitol Hill.
“I remember how the whole office was impressed when she walked in. She was as graceful as a swan and carried a long, slim red umbrella,” gushed Mary Gallagher.
It wasn’t only Audrey’s beauty and grace that attracted JFK. While he though she was “simply exquisite”, it is also said that their sexual chemistry was intense, and quite at odds with her sophisticated public image.
Audrey “had this very sexy, very naughty side that the public never saw,” claims writer Christopher. The two of them made sure their involvement never made it into the gossip columns, and the need for secrecy may even have supercharged the frisson.
Like Marilyn, Audrey is said to have sung Happy Birthday to the President – though at a private event, so there is no record of it. When her former beau was assassinated in 1963, she broke the news to the cast and crew on My Fair Lady, asking everyone to pray for him and reportedly shedding tears inside the prop carriage sitting on set.

Angie Dickinson
JFK’s most enduring affair was allegedly with Angie Dickinson, the stylish star of Rio Bravo (1959) and Ocean’s 11 (1960). She met the future President through her then-boyfriend Frank Sinatra, who was tight with JFK, at a party thrown by Jack’s sister Pat in Santa Monica.
She campaigned for the President across the Midwestern and Plains states in his 1960 campaign and thought of him as “the murderous type, a devastatingly handsome, charming man – the kind of man your mother hoped you wouldn’t marry”. She also described sex with JFK as “the most exciting seven minutes of my life” – though whether this was meant as a compliment is open to interpretation!
The pair are said to have had a serious romance, with a particularly passionate period at the Palm Springs hideaway between JFK winning the election at the start of November 1960 and his inauguration at the end of January 1961. The fishbowl of the White House meant that continuing the affair would have been a dicey prospect, but it’s reported that the two of them shared a private half hour at his inauguration ball at Washington DC’s Statler Hilton hotel.
Angie, now 90, has always declined to say more and at times outright denied the affair. “That’s something I would only discuss with my confessor,” she told a talk-show host in the 1970s.

Anita Ekberg … and the ones who got away
Demonstrating what a close-knit celebrity world he moved in, one of JFK’s lovers was Swedish actress Anita – who was romantically linked to Oleg Cassini, the one-time husband of Gene Tierney, with whom Jack also had a dalliance. Anita was, like Marilyn Monroe, a pin-up known across the world, having starred in Federico Fellini’s lush comedy La Dolce Vita (1960). Her involvement with the President was memorable, if brief.
That’s more than can be said for two other big names, however: Sophia Loren, then 24, turned Jack down twice, while British actress Jean Simmons declared that he practically broke down her hotel room door in his amorous intentions (to no avail). It seems the Kennedy charm only stretched so far – but it certainly took him a very long way in the highest Hollywood circles of the day.