Back in 2015, Madonna finally confirmed a two-decade-long rumor in an interview with Howard Stern: that she had, in fact, dated Tupac Shakur.
While Madonna acknowledged that they dated, she didn't give any further details about their relationship.
And though we might not know any details about the relationship, now we might know why it ended. TMZ published excerpts from a letter Tupac wrote to Madonna while in prison in 1995.
In the deeply personal and emotional letter, Tupac apologizes to Madonna, saying:
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. 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 explain that he felt the pressure to break up with her because she was hurting his "image":
For you to be seen with a black man wouldn’t in any way jeopardize your career, if anything it would make you seem that much more open & exciting. But for me, at least in my previous perception I felt due to my “image,” I would be letting down half the people who made me what I thought I was. I never meant to hurt you… It no longer matters how I’m perceived. Please understand my previous position as that of a young man with limited experience with a extremely famous sex symbol.
He ends the letter by eerily reflecting on taking time for granted:
I don’t know how you feel about visiting me, but if you could find it in your heart, I would love to speak face-to-face with you. It’s funny, but this experience has taught me to not take time 4 granted. ❤️