A Last Minute Decision to Stand in as Rosie Perez’s Date Led to Tupac Shakur’s Relationship With Madonna

Decades after Tupac Shakur’s death, Madonna stepped forward to reveal she had dated the “All Eyez on Me” rapper. The 2015 revelation came as a shock to fans of the iconic singer and late rapper. Since Madonna’s admission, several key players in Tupac’s life have come forward to confirm that the pair did, in fact, date for about a year in the early 1990s. Now, Rosie Perez is explaining how it all came to be.  

Madonna explained her relationship with Tupac Shakur in 2015 

Madonna has had a pretty illustrious dating career. She’s been married and divorced and had a series of high-profile relationships. However, she kept one of her biggest romances under wraps for years. In 2015, Madonna appeared on The Howard Stern Show and revealed that she dated Tupac Shakur for about a year between 1993 and 1994. 

Madonna and Tupac were spotted together multiple times during the year they dated. But neither confirmed the romance at the time. According to a letter written to Madonna by the late star, racism and the complexities of their interracial relationship ultimately led to their split. Their age gap may have played a role in the romance’s demise, too. Tupac was just 23 when he started dating Madonna. She was 36. Tupac died less than two years after he wrote the letter. It took authorities three decades to arrest anyone in his 1996 slaying. He was 25 at the time of his death.  

Rosie Perez said she connected the pair  

Rosie Perez recently appeared on The Drew Barrymore Show. During her interview, she revealed she was Madonna’s wingwoman back in the ’90s. Perez explained that a date stood her up before an awards show. Tupac, her friend, agreed to attend the event with her to make her ex-beau jealous. Madonna happened to be in attendance. 

Perez recalled Madonna approaching her about Tupac, asking if she and the “Changes” rapper were seeing each other. Perez said that when she told Madonna he was simply accompanying her as a friend, she asked to be set up. The Somebody to Love actor helped make the love connection happen. 

While Perez just recently shared the tale with Drew Barrymore, it’s not the first time she recalled playing matchmaker for Madonna. Perez told the same story back in 2015 when she appeared on The View. During that 2015 interview, Perez said Tupac was more than happy to be hooked up with Madonna.