In a handwritten letter the rapper wrote during his final prison bid in 1995, Shakur explained why he was forced to end his blossoming relationship with Madonna.

The letter, which is slated to go on auction with a starting bid of 0,000 on July 19, was revealed publically for the first time by TMZ. In the heartfelt letter, dated January 15, 1995, at a.m., Shakur blamed their racial differences for their breakup.“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 and exciting,” he wrote.

The musicians were seldom seen together, and it wasn’t until a 2015 interview with Howard Stern when Madonna first mentioned actually dating the rapper.

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“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.”The New York rapper acknowledged that he knew he had caused the Michigan-born “Material Girl” heartache, writing that he “never meant to hurt” her.

He also apologized for not being “the kind of friend I know I am capable of being.”Shakur ended the letter extending an olive branch to Madonna and requesting an opportunity to speak with her “face-to-face.”“I don’t know how you feel about visiting me.

We never had an argument backstage." She concluded, "The reimagining of my relationship to Pac has been deeply hurtful." MORE: Katie Holmes Dating Jamie Foxx on the Down Low — Tired of "Sneaking Around" (Photo Credit: Getty Images) The Material Girl revealed she dated Tupac two years before his death to Howard Stern, saying, "I was mad at [David Letterman] when I said the F-word a lot. I was dating Tupac Shakur at the time and the thing is, he got me all riled up about life in general." (Photo Credit: Getty Images) The couple attended the Soul Train Awards together in 1993 — but 15 years after his death Rosie made it clear she was close to Tupac but they were just friends. “I’m grown now, and if it was true I’d say, ‘yeah, we did it.’ Those are rumors, 100%. "My favorite [story] was when him and Lisa were gettin’ into it. I don’t know why he came up with callin’ my girl a boy, but..." star had a fling with the "Changes" rapper.

That’s misogyny in hip-hop — women can’t be friends with guys, apparently.” She continued, "This guy I was supposed to go with to the Music Awards bailed out on me at the last minute... "Extremely smart and funny man who was the utmost gentleman," she wrote on Facebook of Tupac.

He had to leave abruptly and it wasn't to pursue his career.

I've never been to any of Pac's shows by his request. And, let’s hold hands and let that motherf--ker see you on the screen. Watch how crazy I am.’” (Photo Credit: Getty Images) Lisa's TLC bandmate T-Boz opened up about her tumultuous relationship with the rapper. "By the time I made it downstairs she done tore his silk shirt, because that’s when those silk shirts were in, the Versace sweaters and whatnot and all that...By the time the rapper was released from jail, in late 1995, he had already gotten married to a woman named Keisha Morris, whom he had met in New York during his 1994 sexual abuse trial.Shakur and Morris were married in April 1995 while he was serving his four-and-a-half-years prison sentence—of which he only actually served 10 months—and soon after Shakur wrote Madonna from his cell., is still making headlines 11 years after his murder.MORE: Kendall Jenner and A$AP Rocky Have Been Secretly Dating for a Year!The couple had been living together for four months before he was murdered in Las Vegas in September 1996.