Men who loved Marilyn Monroe: The tragic, intense, and lesser-known love stories of the screen icon

Marilyn’s first marriage had nothing to do with Hollywood romance and everything to do with survival. At just 16 years old, still known as Norma Jeane Mortenson, she was facing the prospect of being sent back into a foster home when her guardians prepared to move out of state. To prevent this, an arrangement was made for her to marry her 21-year-old neighbour, James Dougherty. While Dougherty envisioned a quiet life with a traditional housewife, World War II intervened. When he was deployed with the Merchant Marine, Norma Jeane took a factory job, discovered modelling, and quickly outgrew the boundaries of her first marriage. By the time he returned, she was ready to sign her first studio contract, which strictly required her to be single. She eventually filed for divorce, adopted the name 'Marilyn Monroe,' and began her historic ascent in Hollywood.

When America’s biggest baseball legend met Hollywood’s ultimate screen siren, the media obsession was unprecedented. Joe DiMaggio and Marilyn Monroe married in a quiet civil ceremony in January 1954, but their union was a clash of cultures. DiMaggio, fiercely private and traditional, struggled with the hyper-sexualised image his new wife projected to the world. He wanted a stay-at-home wife; she was an ambitious artist at the absolute peak of her career. Though their marriage lasted a tumultuous nine months, their deep bond endured. Following her death, a devastated DiMaggio famously sent roses to her grave three times a week for two decades, never marrying anyone else. DiMaggio remained one of the few fiercely protective, loyal figures in Monroe's life until his own death in 1999.

Everyone was baffled when Marilyn married the brilliant, Pulitzer Prize-winning playwright Arthur Miller in 1956, with headlines famously dubbing the union "Egghead Weds Hourglass." For Marilyn, however, Miller represented the intellectual validation and respect she had spent her career fighting and craving for. She threw herself into the marriage, converting to Judaism and attempting to build a quiet life in Connecticut. But the relationship was strained by professional pressure and deep personal heartbreak, including multiple miscarriages. The final blow came when Miller wrote the screenplay for The Misfits, creating a character that laid bare Marilyn’s real-life emotional fragilities—a move she felt was an intimate betrayal.

Beyond her husbands, Marilyn's dating life involved some of the most influential men, though her closest relationships were often built on mutual understanding rather than tabloid headlines. She shared a brief romance with Marlon Brando in the 1950s that seamlessly transitioned into a lifelong, intensely private friendship. Later, during her painful separation from Arthur Miller, she found comfort in a relationship with Frank Sinatra. Sinatra provided her with an emotional safety net, even giving her a beloved Maltese terrier named "Maf" to keep her company during her loneliest periods.

No chapter of Marilyn’s personal life has generated more conspiracy theories, literature, and controversy than her alleged relationships with the Kennedy brothers. In the final year of her life, rumours swirled that she was involved with both President John F Kennedy and Attorney General Robert F Kennedy. While the exact intimacy of these relationships remains fiercely debated by historians, the intersection of Hollywood's most scandalous star and Washington's highest echelons of power put Marilyn in a dangerous position. Her association with them placed her under intense surveillance by the FBI, transforming her private life from tabloid gossip into a matter of national security just months before her tragic death.