Their connection began in 1969 when the Jackson 5 signed with Motown, a pivotal moment that shaped Michael’s career. Despite rumors that Diana discovered the Jackson 5, it was Motown founder Berry Gordy who made that claim for publicity purposes.

Michael was actually 11 years old at the time, not 9 as some stories suggested.

In the early years of their relationship, Michael lived with Diana Ross for a time, even calling her “Mama.” Diana’s influence on Michael was profound, and he admired her immensely

. He often teased his sisters, Latoya and Janet, saying they were not “pretty” until they looked like Diana. Their closeness continued throughout Michael’s career, but Diana remained a love he could never fully possess. Michael had a deep admiration for Diana, and at one point, he even wanted to marry her. However, their relationship was never fully realized in that way.

There are stories suggesting that Diana and Michael were engaged twice, but both times Diana broke it off. She believed that marrying Michael, who was 14 years younger, might harm her career.

Despite this, they worked together on the film The Wiz in 1977, where their chemistry was evident. There were even rumors of romantic encounters, with Michael staying at Diana’s apartment late into the night. Their relationship was filled with admiration but also a sense of mystery, with both parties remaining tight-lipped about the details.

Michael’s feelings for Diana were intense. He even had a room in his house dedicated to her, filled with photos and paintings, as well as thousands of candles burning for her 24/7.

The obsession with these candles came from an idea he had heard in childhood: that burning candles with a picture of a beloved person would keep them from leaving. Diana’s impact on Michael was undeniable, but their relationship was marked by complexity.

As time went on, Diana married and started a family, which distanced her from Michael. He was hurt by her decision to marry someone else, but he continued to hold a deep love for her.

Their interactions grew more infrequent, and Diana later commented that Michael had become elusive, only reaching out when he wanted something.

The song “Dirty Diana” is often believed to reflect Michael’s heartbreak and frustration with Diana. He wrote it after feeling betrayed by her, especially after she had left him for another man.

The lyrics of the song, particularly the line “She likes the boys in the band,” were a dig at Diana’s history with famous musicians. Michael’s feelings were further complicated by Diana’s jealous actions, such as when she would show up unexpectedly or flirt with him in public.

In the end, their relationship remained full of admiration, but also full of unresolved tension. Michael’s feelings for Diana were deep, but their connection was messy, marked by unspoken love and painful separation.