There was glamorous Jackie, of course. And mother Rose, who nurtured his White House ambitions. And all the others: a movie star, a teenaged intern, a mistress with Mafia ties and more.
Without a doubt, John F Kennedy -- whose assassination 50 years ago in November still looms large in the American consciousness -- had a complicated relationship with women, many women.
Either he embraced them as pillars of strength on his journey to the US presidency, or he toyed with them to satisfy a unfathomable libido, in a "Mad Men" era when alpha males called the shots.
"It depended on the woman," said Larry Sabato, author of the just-published bestseller "The Kennedy Half-Century: The Presidency, Assassination and Lasting Legacy of John F. Kennedy."
"He could be gracious and respectful of those with power and influence," Sabato, director of the Center for Politics at the University of Virginia, told AFP.
"But JFK had a nearly insatiable sexual appetite -- and in our terms today, he treated young and beautiful women as sexual objects."
Central to the Kennedy narrative was Jackie, the former Jacqueline Bouvier, born into affluence in July 1929, who personified style, elegance and sophistication for millions around the world.
The couple married in 1953 when she was a 24-year-old journalist and he was a 36-year-old rookie US senator.
She encouraged him to write the Pulitzer-winning "Profiles in Courage" while recovering from back surgery, and she campaigned alongside him in his hard-fought presidential race against Richard Nixon.
In the White House, she championed the arts and culture, and presided over lavish state functions, while tending to the couple's young children Caroline and his son, John Jr, also known as John-John.
Video: Marilyn Monroe's 'Happy Birthday Mr President'
In the hours after Kennedy was killed, Jackie -- who was sitting next to him in the open-top presidential limousine in Dallas -- famously refused to change out of the pink Chanel suit spattered with his blood.
"I want them to see what they have done to Jack," she said.
Jackie later married Greek shipping mogul Aristotle Onassis.
She died in 1994 at the age of 64, with the John F Kennedy Presidential Library and Museum in Boston remembering her as a selfless woman of duty.
"With a deep sense of devotion to her family and country, she dedicated herself to raising her children and to making the world a better place through art, literature, and a respect for history and public service," reads her profile on its website.
But, while the Kennedys projected a public image of the quintessential modern American family, the president privately surrounded himself with paramours aplenty.
Video -- JFK's women: The Scandals Documentary
Best-known was Marilyn Monroe, the Hollywood sex goddess who got tongues wagging with her sultry rendition of "Happy Birthday" at a 1962 Democratic Party fundraising soirée.
The presidential birthday boy made no effort to conceal his delight.
Jackie not only knew of the liaison, but told Monroe she was welcome to have her man, according to journalist Christopher Andersen's recent book "These Precious Few Days: The Final Year of Jack with Jackie," published in August.
"And you'll move into the White House and you'll assume the responsibilities of first lady, and I'll move out and you've have all the problems," she reportedly told Monroe, who died of a drug overdose later in 1962.
Those "problems" might have included Judith Campbell Exner, whose claim of a steamy two-year affair with Kennedy -- coinciding with a relationship with a Chicago underworld kingpin -- is deemed credible by historians. She died in 1999 at the age of 65.
Or Mimi Beardsley, a 19-year-old White House intern when Kennedy wooed her into an affair that lasted 18 months. She was a virgin, she said, when they first made love on Jackie's bed; later the two would race rubber duckies in the presidential bath tub.
Video: JFK's affair with a White House intern
"I do not regret what I did. I was young and I was swept away, and I cannot change that fact," said the future Mimi Alford in her 2012 memoir, "Once Upon a Secret: My Affair with President John F. Kennedy and its Aftermath."
No-one knows how many prostitutes Kennedy hired, but there were enough for his bodyguards to worry that he might fall victim to espionage or blackmail, at a time when the United States and the Soviet Union stood on the brink of nuclear war.
"He had a tendency to surround himself with ladies sometimes who were a little worrisome," said one Secret Service agent, Anthony Sherman, in an ABC television documentary in 1997.
"These women were of questionable character," added another, William McIntyre.
"This was reckless to the extreme," Sabato told AFP.
"JFK risked his presidency and family over and over... Almost certainly, foreign intelligence agencies had some knowledge of this pattern of behavior."
No doubt his mother did. Rose Kennedy is credited with infusing a strong sense of history and public service into all her children. Fascinated by politics, she actively took part in JFK's election campaigns, stumping the hustings, soliciting votes.
Like Jackie, she tolerated the promiscuous conduct of the family patriarch, business tycoon and ambassador Joseph Kennedy, whose three-year affair with screen idol Gloria Swanson in the 1920s presaged the Marilyn-JFK fling.
A devout Roman Catholic, Rose Kennedy died in 1995 at the age of 104, outliving four of her nine children.