Michael Jackson & Diana Ross: Their Untold Love Story

In the world of music, few relationships have captured the imagination of fans as much as that of Michael Jackson and Diana Ross. Their connection, which began in the innocence of childhood, evolved into a complex tapestry of admiration, infatuation, and unrequited love. This story delves into the nuances of their relationship, exploring the depths of Michael’s feelings for Diana and the impact she had on his life and career.

Michael Jackson’s affection for Diana Ross can be traced back to his childhood. Growing up in the spotlight as a member of the Jackson Five, Michael was introduced to the world of fame at a young age. His brother, Jermaine, recounted in his memoirs that Michael’s love for Diana started as a simple childhood crush. “They only became close when Michael came of age,” Jermaine wrote. “I know Michael has always loved Diana; from when he was a small boy, he knew he wouldn’t be able to act on his love for her until he became an adult.”

This early admiration blossomed into a teenage infatuation, fueled by the allure of Diana’s stardom. By the late 1970s, the media was rife with speculation about the nature of their relationship. Were they merely friends, or was there something more? The flirtation between the two icons was palpable, and fans were eager to uncover the truth behind the headlines.

Michael first met Diana Ross at the tender age of 10 during an audition for Motown Records. Diana, already a superstar, was a guiding light for the young Jackson Five. The story that circulated in the media—that Diana discovered the Jackson Five and used her connections to propel them to fame—was largely exaggerated. However, it was undeniable that Diana played a significant role in their early careers.

As the Jacksons settled in Los Angeles, Michael moved in with Diana, who became a mentor and a source of inspiration for him. He would often tease his brothers, calling her his “girlfriend” and playfully asserting his claim over her. This playful banter masked a deeper longing that Michael harbored for Diana, a longing that would only intensify as the years went by.

In 1977, Michael Jackson accepted the role of the Scarecrow in the film adaptation of “The Wiz,” a decision heavily influenced by Diana, who was cast as Dorothy. Their collaboration on the film brought them even closer, as they spent long hours together on set. The chemistry between them was undeniable, and they were often seen attending parties together, including the infamous Studio 54 nightclub in New York.

During the filming, Diana’s assistant recounted a moment when they were late for a shoot, only to discover that they had spent the night together in Michael’s apartment. This incident fueled rumors of a romantic relationship, but the truth was more complicated. Diana, who was 13 years older than Michael, struggled with the implications of their age difference and the public perception of their relationship.

While Michael was infatuated with Diana, she was hesitant to take their relationship seriously. The 13-year age gap loomed large in Diana’s mind, and she was acutely aware of how their connection would be perceived by the public. Diana was a fiercely ambitious woman, and the thought of being seen as a romantic partner to a much younger man was daunting.

Despite her reservations, Diana’s affection for Michael was genuine. She often praised him in interviews, calling him a “gentle, wonderful human being” and expressing her admiration for his talent. However, the flirtation that characterized their interactions was often misconstrued by fans as something more than friendship.

Michael’s infatuation with Diana reached a point where he erected a shrine in his family home dedicated to her. This shrine was filled with photographs and mementos, a testament to the deep emotional connection he felt towards her. Despite Diana’s attempts to soften the blow of their relationship, Michael remained convinced that they were destined to be together.

In a candid interview, Michael expressed his feelings for Diana, saying, “Diana Ross is everything you could wish for. I love her. I hope she marries me. She always tells me her most private secrets. That’s the kind of relationship we have.” This declaration revealed the depth of his feelings, but it also highlighted the naivety of his perspective.

The turning point in their relationship came in 1985 when Diana met Norwegian shipping magnate Arne Næss Jr. The two married the following year, and Michael was devastated. He had always harbored hopes of a future with Diana, and her marriage felt like a betrayal. In a moment of vulnerability, he admitted, “When I heard Diana Ross was getting married, I was happy for her because I knew it would make her very joyous. Still, it was hard for me, getting married to this man I’d never met. I wanted her to be happy, but I have to admit that I was a bit hurt and a little jealous.”

Michael’s emotional turmoil was evident during the 1986 American Music Awards, where he appeared visibly upset and cold towards Diana. The juxtaposition of their past intimacy and the reality of her marriage created a rift that would be difficult to bridge.

In the years that followed, Michael channeled his feelings for Diana into his music. He wrote several songs that reflected his complex emotions, including “Remember the Time,” which was inspired by his love for her. Jermaine Jackson, Michael’s brother, noted that the song was written with Diana in mind, representing the one great love that had eluded him.

Another notable track, “Dirty Diana,” released in 1987, was interpreted by many fans as a dig at Diana Ross. The lyrics conveyed Michael’s anger and frustration at feeling led on, only to see her marry another man. Despite the pain, Michael’s love for Diana remained a constant theme in his life and work.

Despite the distance that grew between them, Michael and Diana maintained a bond that transcended time and circumstance. Diana’s marriage to Arne was not without its challenges, and she often found herself longing for the connection she had with Michael. In interviews, she expressed her admiration for him, stating, “I’m crazy about Michael and I love him a lot. He’s been my inspiration.”

As the years passed, their interactions became less frequent, but the affection remained. In 1991, Diana remarked, “When he wants to see me, he sees me; when he doesn’t, he kind of closes the door. There’s no reaching him, there’s no finding him, there’s no anything. He’s just this elusive love out there.” This sentiment encapsulated the bittersweet nature of their relationship—two souls forever intertwined yet separated by the complexities of life.

In 1995, during a hospital visit, Michael’s affection for Diana was on full display. He had his then-wife, Lisa Marie Presley, removed from the room in preparation for Diana’s arrival. The warmth and love he showered upon her during this visit were a testament to the enduring bond they shared. Michael referred to Diana as his “world,” a phrase that underscored the significance she held in his life.

After Michael’s untimely death in 2009, Diana was mentioned in his will, a gesture that spoke volumes about their relationship. He expressed a desire for her to care for his children in the event of his mother’s passing, recognizing Diana as a guiding figure in his life. This act honored their lifelong friendship and the special place she held in his heart.

The story of Michael Jackson and Diana Ross is one of unrequited love, admiration, and the complexities of human relationships. Their connection, forged in the fires of fame and ambition, transcended the boundaries of friendship and flirtation. While Diana may not have reciprocated Michael’s romantic feelings, their bond was undeniably profound.

As fans continue to celebrate the legacies of these two iconic figures, their story serves as a reminder of the power of love—both its beauty and its heartache. Michael Jackson’s infatuation with Diana Ross may have been a bittersweet chapter in his life, but it remains a testament to the enduring impact of love and the connections we forge along our journeys.