Madonna's history of dating much younger men is legendary, and she continued her streak when she became romantically involved with back-up dancer Ahlamalik Williams. In this case, however, not only is she older than the object of her affection, but she is also older than both of his parents. When Williams' parents met his lady in 2019, Madonna was 61, Williams' dad Drue was 59, and his mom Laurie was 55. His parents were unbothered by the decades separating the two, however, and Drue told The Mirror, "We know there's a huge age gap between the two — 36 years. Madonna is two years older than me." He also said, "But I have told my son love doesn't have an age range when you're consenting adults."

Interestingly, Drue reported to TMZ that by the end of 2019 the couple had actually been dating for over a year, which differs from most outlets' reporting that the couple only got together at the end of that year. Drue also revealed in his interview with The Mirror that they had been introduced to Madonna in New York after one of her shows. He also told TMZ, "Love has no age," and, "My son is livin' la vida loca, and I'm just happy for him."