2Pac & Madonna’s Secret Romance Began Thanks To Soul Train Awards Twist 

Tupac Shakur and Madonna once shared a secret two-year romance, but they never would have hooked up if the rapper wasn’t on a date with another woman the night the music icons met.  

Actor Rosie Perez recently spilled the tea about the former couple during a recent appearance on the “Drew Barrymore Show.” 

Perez explained that the late rapper, who was tragically killed in 1996, met the superstar singer at the Soul Train Music Awards in 1993. However, the story begins with Perez getting stood up by a man who bailed on her because he feared his girlfriend would find out about their date.  

Perez said her “good friend” Tupac Shakur called her just after she got off the phone with her date. He immediately offered to take his place, saying, “You know what, I’m gonna go with you. We’re gonna walk up in there, we’re gonna act like we’re on a date, and he’s going to die.” 

Once the pair arrived at the awards ceremony, Perez said her “dear friend” Madonna wasted no time getting the low down on her date. 

“She came up to me and was like, ‘Yo, what’s up?” Perez recalled. “Y’all are together?’” 

Once Perez explained that Shakur were just friends, Madonna responded, “Hook me up.” Perez obliged, and the rest was history.  

Tupac Shakur Broke Up With Madonna In A Letter From Jail

Tupac Shakur broke up with Madonna while he was in jail facing a sexual assault charge in 1995. He wrote a letter to the singer indicating racial differences played a role in their split.  

“For you to be seen with a black man wouldn’t in any way jeopardize your career,” he wrote in part. “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 thought I was.”