2. Madonna & Ahlamalik Williams

While many may assume that Madonna may have stopped being romantically involved given her age, it seems that many may be shocked to know that she has been romantically involved with Ahlamalik Williams. Williams, who is 27, first met Madonna, who is 62, back in 2015 when he worked as a dancer. However, they only started dating in 2018. Immediately, many took notice of their 35-year age gap, which is not unusual for Madonna. In fact, Williams is just two years older than one of Madonna’s children, showing just how large their age gap is.

Despite this, they managed to maintain a loving and caring relationship for years. Not much is known about their relationship, as they tend to keep it very private. They only tend to publish their romance on special occasions like Valentine’s Day. Overall, it seems that they have made a good investment in keeping their relationship strong.