Diana Ross
While he was still in a relationship with Cher, Simmons met another famous singer, Diana Ross. In fact, Simmons initially hung out with Ross when he asked her to help him find a Christmas present for his girlfriend at the time. What was supposed to be a trip to the mall led to a full-blown romance between the two.
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Simmons and Ross dated for about three years, and, throughout that time, they were seemingly very happy together. Simmons even helped his talented girlfriend leave her record company and land the biggest recording contract in history (at the time). The couple split when Diana’s desire for a family conflicted with Simmons’ free spirit.