Madonna and rapper Vanilla Ice
Madonna started dating the rapper Vanilla Ice in 1991 and split after eight months of being together. Vanilla Ice later claimed in an interview that his ex proposed to him.
Madonna and Dennis Rodman
Madonna and Dennis Rodman, the two rarely commented on their past romance, however they reportedly dated for two months in 1994
Madonna and Ahlamalik Williams
Queen of pop Madonna split from her boyfriend Ahlamalik Williams after three years of togetherness. The couple — who have a 35-year age gap — started dating in 2019 and Madonna regularly shared photos of him on social media