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.