Madonna sought Rosie Perez's help to connect with Tupac Shakur in 1993

Madonna sought help from Rosie Perez to connect with Tupac Shakur in 1993. After Rosie’s date canceled last minute, Tupac offered to accompany her to the Soul Train Music Awards as a "wingman." At the event, Madonna approached Rosie and asked to be set up with Tupac. This led to a secret relationship between Madonna and Tupac that lasted until 1994. A letter from Tupac revealed he ended the romance due to concerns about race and public perception. He expressed that being seen with a black man could harm his image, despite believing it would benefit Madonna's career.