Inside Jackie Kennedy’s Extensive Dating History, Affairs & Flings With Hollywood Legends

John P. Marquand

Years before becoming First Lady, Jackie lost her virginity to John P. Marquand, the son of famous novelist John Marquand Sr. “Jackie, when she was a teenager, lost her virginity to somebody in Paris in an elevator,” author J. Randy Taraborrelli told People Now in January 2018. “It wasn’t the most romantic experience, but it was a good one for her, and she was really happy that she had it.”

John Husted Jr.

In the early 1950s, Jackie had her first engagement with John Husted Jr., a stockbroker she met after attending Vassar College, People reports. The pair split, however, once Jackie discovered how little money he made and deemed it insufficient. Right after, she slipped him her ring and broke things off. “She was ice cold,” John remembered, per Taraborrelli. “Like we never knew each other.”

André Malraux

While studying abroad in Paris during her junior year in college, Jackie developed a romantic connection with French novelist André Malraux. “He’s the only Frenchman I’ve met that I truly wanted to marry,” she said, per Daily Mail via  Jacqueline Kennedy Onassis: A Life Beyond Her Wildest Dreams by Darwin Porter and Danforth Prince.

Ormande de Kay

Prior to her wedding with JFK, Jackie also dated Ormande de Kay, a young American she agreed to wed after his return from the Korean War. After meeting her future husband, however, Jackie wrote him a letter ceiling it off. “I want you to be the first to know that I’ve found the love of my life, the man I want to marry,” she wrote, per Porter and Prince. “I am now engaged to John F. Kennedy.”

John F. Kennedy

Jackie then went on to meet John F. Kennedy in 1952 and the two tied the knot a year later in 1953. Despite being together throughout his presidency and until his assassination in 1963, the two were also infamous for having affairs outside their marriage. 

Peter Lawford

According to the 2014 book Jacqueline Kennedy Onassis: A Life Beyond Her Wildest Dreams by Darwin Porter and Danforth Prince, Jackie had her fair share of A-list affairs during her marriage with JFK, Daily Mail reported. Among her rumored flings was with film actor Peter Lawford. 

Gregory Peck

Another one of Jackie’s rumored affairs was with actor Gregory Peck. 

William Holden

According to Jackie’s close friend Bill Walton in Porter and Prince’s book, Jackie also had a brief fling with actor William Holden “primarily driven by Jackie’s desire to seek revenge on Jack” for his cheating.

Marlon Brando

In Bobby and Jackie: A Love Story by C. David Heymann, the author broke down the short-lived relationship between Jackie and acting legend Marlon Brando. The extract was previously included in the Oscar winner’s 1994 memoir, Songs My Mother Taught Me, but was eventually cut. ”She kept waiting for me to try to get her into bed,” Brando said of Jackie. “When I failed to make a move, she took matters into her own hands and popped the magic question. ‘Would you like to spend the night?’ And I said, ‘I thought you’d never ask.'”

Gianni Agnelli

According to Portner and Prince, Jackie took a vacation with Fiat tycoon Gianni Agnelli following Marilyn Monroe’s sexy rendition of “Happy Birthday Mr. President” to JFK in 1962.

Roswell L. Gilpatric

Jackie was also rumored to have an affair with Roswell L. Gilpatric, the Deputy Director of Defense in the Kennedy Administration.

Pete Hamill

Jackie was also rumored to have dated Pete Hamill, an American journalist and former boyfriend of Shirley MacLaine.

Robert F. Kennedy

Following JFK’s death, his brother Robert F. Kennedy, aka Bobby Kennedy, moved into Jackie’s home to show her some support. With time, the two were rumored to have developed a relationship as well. “Jackie and Bobby were definitely having an affair,” Jackie’s close friend, Nancy Dickerson confirmed to Porter and Prince.

Jack Warnecke

A few years later, Jackie hired architect Jack Warnecke to design JFK’s new tomb and, with time, the two began a relationship. According to Taraborrelli, the two later split after Warnecke revealed he was deeply in debt. 

Lord Harlech

Also in the years following JFK’s death, Jackie was romantically linked with David Ormsby-Gore, also known as Lord Harlech, a former British ambassador. It was later revealed in a handwritten letter by Jackie that she turned down Harlech’s proposal to be with her future husband Aristotle Onassis.

Paul Newman

According to Porter and Prince, Jackie went on to have a one-night affair with actor Paul Newman in 1968 at New York’s Carlyle Hotel. Although there was a clear connection between them, Jackie reportedly used her sexual charms to urge Newman to shift his political allegiance to Senator Robert Kennedy. 

Ted Kennedy

In Porter and Prince’s book, it was revealed for the first time that Jackie also lived a relationship with former Senator Ted Kennedy before and after Bobby’s murder, Daily Mailreported. “Teddy stood by Jackie through one crisis after another, becoming the one man in her life she could depend on,” the authors wrote. 

Jackie, for her part, became quite conflicted. “I’m in love with two men at the same time, both Bobby and Teddy,” Jackie reportedly told novelist Truman Capote. 

Aristotle Onassis

In 1968, Jackie shocked the world when she married shipping tycoon Aristotle Onassis and officially became “Jackie O.” The two, who had an age difference of 23 years, were together for six and a half years until Onassis died in 1975 of respiratory failure. 

Warren Beatty

In a new excerpt obtained by People from Taraborrelli’s new biography Jackie: Public, Private, Secret, it was revealed that Jackie had a brief fling with actor Warren Beatty in the mid-1970s. Despite his stardom, however, Jackie was unimpressed. “All he wanted to do was talk about directors and producers and films, and she just wasn’t into any of that,” Taraborrelli wrote. 

Frank Sinatra

Jackie also had a short-lived affair with legendary singer Frank Sinatra. The two reportedly shared one romantic night in 1975. 

Maurice Tempelsman

Maurice Tempelsman, a diamond merchant, was the last love of Jackie’s life. After returning to New York City following Onassis’ death, Tempelsman and the former First Lady found a true connection. The two were together for 12 years until her death from cancer in May 1994. Tempelsman gave a eulogy.