Yes, these two secretly dated in the ’90s!
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.
The two reportedly dated for about a year, from 1994-95. Neither of them ever commented publicly on it at the time. And Tupac was killed the following year.
While Madonna acknowledged they dated, she did not give any further details about their relationship.
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.