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A few years ago, Madonna revealed on Howard Stern’s radio show that she dated the late Tupac Shakur for a spell in the mid-’90s. Others confirmed it, too: both actress Rosie Perez and Shakur’s brother, Mopreme Shakur, revealed that they played roles in hooking the pair up. Still, the nature of their relationship has remained vague. A new letter, published on Wednesday by TMZ, changes that.

Written in 1995 while Shakur was serving time for sexual assault at the Clinton Correctional Facility, the letter first addresses the reason why he put an end to their relationship. Read an excerpt below:

Can u understand that? 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 of the people who made me what I thought I was. I never meant to hurt you.


Shakur also references an interview where Madonna said she wanted to “rehabilitate all the rappers & basketball players.” He continues, “It was at this moment out of hurt & a natural instinct to strike back and defend my heart & ego that I said a lot of things…Please understand my previous position as that of a young man with limited experience with an extremely famous sex symbol.”

Various sections of the letter are redacted, but what we see essentially functions as an earnest, heartfelt attempt to reconnect, as he asks for her friendship and even asks if she’d be comfortable visiting him in prison. Throughout his career, Shakur balanced his hardened shell and legal troubles with a deep sense of vulnerability; this letter serves as yet another example of the rapper’s probing introspection.

If you’re dying to read the redacted sections, simply pop over the Gotta Have Rock And Roll auction, where it holds a starting bid of $100,000.

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