Michael Jackson’s love for Diana Ross was more than just admiration for a fellow artist—it was a deep, romantic infatuation that began in childhood and lingered throughout his life. What started as a young boy’s innocent crush evolved into a complex and emotionally intense connection that would shape Jackson’s personal life and creative journey for decades.

Michael first met Diana Ross at the age of 10 during the Jackson 5’s audition for Motown Records, where Diana was already a reigning superstar. Though Berry Gordy officially discovered the Jackson 5, Motown crafted a narrative that Diana was their discoverer to help propel them to fame. Michael later moved in with Diana while his family settled in Los Angeles, and he often called her his “girlfriend,” refusing to let anyone else near her.

Their bond deepened over time, especially during their work on the 1978 film The Wiz, in which Diana played Dorothy and Michael played the Scarecrow. Critics and insiders speculated that Diana secured the film role under the condition that Michael would star alongside her. During the shoot, the pair were often seen at Studio 54, and one of Diana’s assistants even discovered them together one morning after a night out—sparking rumors of a more intimate relationship.

Despite the chemistry, Diana never publicly acknowledged a romantic involvement. She cited the 13-year age gap and the fact that she had known Michael since he was a child. Nevertheless, Michael’s feelings persisted. He would erect a shrine to her in his family home and continued to refer to her with deep affection, even saying in an interview, “I hope she marries me.”

In 1981, during her television special, Diana embraced Michael with warmth and flirtation onstage, calling him “my baby.” Their dynamic, though playful and loving, was often misconstrued by the public as romantic. According to Michael’s brother Jermaine, Michael’s infatuation with Diana was profound and enduring, and he believed she was his one true love.

The turning point came in 1986 when Diana married Norwegian businessman Arne Næss Jr. Michael was devastated and reportedly canceled his attendance at the wedding last minute. In his autobiography Moonwalk, he admitted feeling jealous, although he wanted Diana to be happy.

Still, he channeled his emotions into his music. The 1992 hit “Remember the Time” was reportedly inspired by Diana, representing a love that “escaped him.” The controversial “Dirty Diana” was also rumored to be a reflection of his frustration with her, though officially about groupies.

Despite Diana’s marriage, the two stayed in contact, though less frequently. Michael remained emotionally attached, even going as far as kicking out then-wife Lisa Marie Presley from his hospital room in 1995 to prepare for Diana’s visit. He called her “his world,” lavishing her with gifts and affection.

Diana, for her part, acknowledged their deep bond. She described Michael as an “elusive love” and a “wonderful human being” whose aura was “only about love.” Though she never confirmed a romantic relationship, the fondness between them was undeniable.

After Michael’s death in 2009, Diana Ross was named in his will as the guardian of his children if his mother, Katherine, was unable to care for them. This touching gesture underscored the lasting impact Diana had on Michael’s life—a symbol of trust, love, and the motherly figure he cherished.

Their story is one of unrequited love, deep emotional ties, and enduring friendship. Whether romance ever blossomed behind closed doors remains unknown. But to Michael Jackson, Diana Ross was always the one that got away.