#32: He Dates Diana Ross in the Early 1980s and Studies Her Discipline
In the early 1980s, he dated Diana Ross, making their relationship another major celebrity romance in his public life. Ross was already a Motown legend and solo star, while KISS was moving through a period of reinvention and internal change.

Simmons later spoke admiringly about Ross’s discipline, control, and command over her career. That admiration fit his own growing interest in business, branding, and self-management. The romance did not last forever, but it placed him close to another performer who understood how fame could be shaped.
