Who Were Marilyn Monroe's Most Famous Lovers? Revisiting Her Relationships and Rumored Affairs

From John F. Kennedy to Jerry Lewis, a look at Marilyn Monroe's great loves and alleged flings

Over the years, Marilyn Monroe's love life has become as shrouded in mystery and legend as the circumstances of her death on Aug. 4, 1962.

Despite the constant whispers about the Blonde Bombshell’s alleged lovers, even Monroe understood her power to refuse to kiss and tell. Plus, as her good friend and photographer Sam Shaw — who himself was rumored to be her lover — once said: "If Marilyn slept with every guy that claims he was with her, she would have never had time to make any movies."

That said, let’s look back on the most famous men (and women) who have been lucky enough to be linked to Hollywood's greatest sex symbol.

Jim Dougherty

Monroe was 16 years old and still known as Norma Jeane Baker when she married Jim Dougherty, a classmate at Van Nuys High School, in 1942.

Their relationship began to disintegrate when Dougherty joined the Merchant Marines and she began modeling. They were divorced by 1946.

"If I hadn't gone into the Merchant Marines during World War II, she would still be Mrs. Dougherty today," he told PEOPLE in 1976.

Charlie Chaplin Jr.

Rumor has it that Monroe had an affair with the legendary Charlie Chaplin's son, Charlie Jr., in 1947. The relationship allegedly ended when Charlie caught Marilyn in his brother Sydney's bed.

Charlie referenced the affair in his autobiography, and Anthony Summers mentions the relationship in his book Goddess: The Secret Lives of Marilyn Monroe.

The alleged romance was also explored in Blonde (2022), starring Ana de Armas in an Oscar-nominated role as Monroe, based on Joyce Carol Oates’ 2000 novel of the same name. Although unconfirmed, the film depicted Monroe in a three-way relationship with Charlie and Edward “Eddy” G. Robinson Jr.

Milton Berle

Milton Berle and Monroe first met on the set of Ladies of the Chorus in 1948. Although the comedian was officially dating film star Adele Jergens at the time, Berle claimed to have had a brief affair with the young actress.

Berle, the first superstar of the TV era (and, according to Truman Capote and showbiz lore, famously well-endowed), also starred with Monroe as himself in the aptly titled film Let's Make Love in 1960.

"Marilyn was on the climb in Hollywood, but there was nothing cheap about her," he wrote in his 1975 autobiography. "She wasn't one of the starlets around town that you put one meal into and threw into the sack. Maybe she didn't know exactly who she was, but she knew she was worth something. She had respect for herself. Marilyn was a lady."

Natasha Lytess

Monroe met Natasha Lytess, her beloved drama coach, when she signed a short contract with Columbia Pictures in 1948. The duo would become nearly inseparable on and off set over the next seven years, sparking rumors of a relationship.

The actress' dependence on Lytess grew so intense that she began refusing to film scenes without her coach nearby. The speculation continued when Monroe moved into Lytess' home to prepare for her role in Don't Bother to Knock (1952).

While the nature of their relationship remained a mystery, Lytess was openly hostile to Monroe's male suitors, especially Joe DiMaggio.

"She was a great teacher, but she got really jealous about the men I saw. She thought she was my husband!" Monroe once said of her teacher, with whom she eventually parted ways in 1956.

As for rumors of other lesbian affairs with Barbara Stanwyck and Marlene Dietrich, Monroe seemingly put the issue to rest in her autobiography, My Story, which was released in 1974. "A man who had kissed me once had said it was very possible I was a lesbian because I apparently had no response to males — meaning him," she wrote. "I didn't contradict him because I didn't know what I was. … Now, having fallen in love, I knew what I was. It wasn't a lesbian."

Elia Kazan

Elia Kazan, one of Hollywood's all-time great directors, admitted to having a brief affair with a young Monroe while he was married to playwright Molly Thacher.

Per The Hollywood Reporter, Kazan confessed in unearthed private letters to Thacher that he slept with the actress, writing, "I'm not sorry about it."

He added: "I'm not ashamed at all, not a damn bit, of having been attracted to her. She is nothing like what she appears to be now, or even appears to have turned into now. She was a little stray cat when I knew her."

Kazan was a close friend of Monroe's future husband, Arthur Miller, and also referred to DiMaggio in his letters to Thacher, saying the ballplayer beat up Monroe "several times."

The Kennedy brothers

Monroe's most infamous rumored affairs were with former President John F. Kennedy and later his brother, Attorney General Robert F. Kennedy. Some have even suggested that her relationship with the two men played a role in her untimely death.

Rumors of an affair were spurred in part by her sultry "Happy Birthday" performance for the commander-in-chief at his 45th birthday celebration at Madison Square Garden on May 19, 1962, just months before her death.

Monroe biographer James Spada told PEOPLE in 2012 that while he doesn't believe there's any proof that the Kennedys were responsible for Monroe's death, "it was pretty clear that Marilyn had had sexual relations with both Bobby and Jack."

In his 2023 biography, Jackie: Public, Private, Secret, J. Randy Taraborrelli revealed a surprising connection between Monroe and the former president’s wife, Jacqueline Kennedy Onassis. As it turned out, both women shared the same therapist, Dr. Marianne Kris, whom Jackie began seeing for her PTSD following her husband’s assassination.

"When Jackie confronted her," Taraborrelli wrote, "[Dr.] Kris said she felt no responsibility to inform her about any former patients in the same way she'd never reveal that she'd ever treated Jackie. Marianne asked, 'How is this relevant?' to which Jackie responded, 'How is that not relevant?' "

Joe DiMaggio

She was "like a good double-play combination," the baseball great DiMaggio told a friend after he and Monroe were introduced on a blind date in 1952.

Six months into retirement, he saw the then-26-year-old actress, in the words of the late prolific biographer Donald Spoto, as "a beautiful blonde showgirl who might double as a devoted mother and homemaker."

Monroe, who also longed for a home and children, was surprised by the famous ballplayer. "I expected a flashy New York sports type, and instead I met this reserved guy who didn't make a pass at me right away," she said of DiMaggio in Spoto’s 1993 biography of her. "He treated me like something special."

They married on Jan. 14, 1954, in a quiet ceremony at City Hall in his native San Francisco. But problems arose as DiMaggio, accustomed to being the biggest star in the room, became bothered by his wife's skyrocketing fame.

The couple divorced that October, nine months after their wedding. Monroe later said her now-infamous billowing skirt scene in The Seven-Year Itch (1955) was the final point of contention: "He said … exposing my legs and thighs, even my crotch — that was the last straw."

Yet they remained close friends, and for 20 years after Monroe's death, DiMaggio sent roses to her grave three times each week.

Marlon Brando

Perhaps the two most famous actors of their generation, Monroe and Marlon Brando were rumored to have briefly dated in 1955, after her divorce from DiMaggio and before her relationship with Miller.

Brando escorted Monroe to the premiere of The Rose Tattoo (pictured), and the two remained friendly until the end of her life.

Arthur Miller

Monroe would later say it was love at first sight when she met the author and playwright in 1950 on the set of As Young As You Feel (1951).

The duo did not reconnect until 1955 after she had divorced DiMaggio and moved from Hollywood, Calif., to New York City. They began secretly dating and were married in 1956.

"We're so congenial, this is the first time I've been really in love. Arthur is a serious man, but he has a wonderful sense of humor. We laugh and joke a lot. I'm mad about him," she’s quoted as saying of Miller in 1956 in Jane Russell’s 1989 book, Marilyn Monroe and the Camera.

At first, Monroe flourished away from Hollywood in her more normal life. She began cooking, cleaning and caring for Miller's children, who all loved spending time with her. But when Monroe returned to work on The Misfits (1961), written by Miller, their relationship began to crumble.

Monroe's drug addiction caused problems on set and at home, and shortly before the film's premiere, she and Miller divorced after five years of marriage. Just 19 months later, Monroe fatally overdosed.

Frank Sinatra

The Blonde Bombshell and Ol' Blue Eyes briefly dated after her divorce from Miller.

After her split from the playwright, Monroe stayed at Frank Sinatra’s house for a time after moving back to Los Angeles. The romance cooled off by 1961 when the crooner proposed to Juliet Prowse, but the two remained friends until her death.

Jerry Lewis

Late comedian Jerry Lewis claimed to have had a secret love affair with Monroe during a candid 2011 GQ interview.

First, Lewis insisted that Monroe's affair with former President Kennedy never happened, saying, "I'm telling you what I know. Never! And the only reason I know is because I did. Okay?"

When the interviewer reacted with disbelief, Lewis assured the story was true, saying that Monroe used sex like he used humor: "She needed that contact to be sure it was real."

So what was the affair like?

"It was … long," he said. "I was crippled for a month." After another pause, he quipped, "And I thought Marlene Dietrich was great!"

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