In Tupac’s short 25 years of life, the West Coast hip-hop idol had been linked to relationships with few women on his rise to rap royalty, such as Quincy Jones’s daughter, Kidada.

But before sparking a relationship with the then-21-year-old, Pac’s steamy affair with pop songstress Madonna lit up headlines. Now that TMZ has reportedly obtained a letter from Pac to the Rebel Heart artist, we now have an idea as to what blew out their short-lived flame. 

The letter was reportedly written during the All Eyez on Me rapper’s 1995 jail stint, as it’s dated from Jan. 15, 1995, in the upper right-hand corner. Expressing his deepest regret to the Material Girl, Tupac began by explaining all the words it took to muster up the letter and apologizing to her.

“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 wrote in the first half of the letter.

After a section of the letter is blurred out from TMZ, the next section reveals his true reason for needing to call it quits: he was Black, Madonna is white.

“Can you understand that?” he asks. “For you to be seen with a Black man wouldn’t in anyway jeopardize your career, if anything it would make you seem that much more open and 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 was. I never meant to hurt you.”

Later on in his message, he mentions an interview from Madonna that he admitted caused himself a bit of hurt as well. According to Pac, she stated that she was “off to rehabilitate all the rappers and basketball players,” a reveal that shocked him because he believed he had been the first rap artist she dated.

“It was at this moment out of hurt and a natural instinct to strike back and defend my heart and ego that I said a lot of things…”

The rest of the letter is spent explaining his growth from their previous relationship, and even threw in a “but we can be friends” offer instead. Concluding the three-page letter, he extends an invitation for her to visit him so that they can discuss the break-up face-to-face, if she was up to it.

As most of Tupac keepsakes have, TMZ adds that the letter will be available for auction toward the end of July with bids starting at $100,000.

Read Pac’s full letter breaking things off with Madonna here.