Tupac Shakur and Madonna were romantically involved in the early 1990s. Their relationship was not widely known at the time but was later confirmed by both Madonna and the late rapper’s brother, Mopreme Shakur.

In 2015, Madonna revealed in an interview with Howard Stern that she dated Tupac briefly in the early 1990s. Their relationship is believed to have taken place around 1993–1994, during Tupac’s rise in the rap industry and Madonna’s continued success in pop music. The relationship was kept mostly private, possibly due to the contrasting public images of both artists.

In 2017, a letter Tupac wrote to Madonna from prison in 1995 surfaced. In the letter, Tupac explained that he ended their relationship because he felt that dating a white woman, especially someone as famous as Madonna, could hurt his image and credibility in the Black community. He expressed regret and admiration for Madonna but stated that he needed to move on for personal and cultural reasons.

Penned on Jan. 15, 1995 while Shakur was at the Clinton Correctional Facility, where he was serving time on 𝓈ℯ𝓍ual abuse charges, the letter begins with an apology: “I’ve waited a long time 2 finally write this mainly because I was struggling to find all the answers so that I wouldn’t leave any unanswered questions,” he wrote. “First and foremost, I must apologize to you because like you said I haven’t been the kind of friend I know I am capable of being.” He goes on to describe their split as the consequence of how an interracial relationship might impact their respective careers—and especially his.

“For you to be seen with a black man wouldn’t in any way jeopardize your career,” he wrote. “But for me at least in my previous perception I felt due to my ‘image’ I would be letting down half of the people who made me what I thought I was.”

And while he describes himself as “a young man with limited experience,” the rapper also offers his sage advice, warning Madonna “not everyone is as honorable as they seem.” Their split, judging by the apologetic tone of the letter, was none too amicable, yet by the end of the letter the rapper seems prepared to put it behind them. Tupac closes the letter offering his friendship again to Madonna, admitting he had “grown both spiritually and mentally. It no longer matters how I’m perceived.”

Madonna has spoken positively about Tupac in interviews, stating that he was a kind and charismatic person. The breakup letter was later put up for auction, and was sold for more than $170,000, despite Madonna’s legal attempts to block its sale. Tupac was tragically 𝓀𝒾𝓁𝓁ed in 1996, and Madonna has since acknowledged their brief romance as part of her past.