From Madonna to Rashida Jones's Sister, a Look Back at Tupac Shakur's Many Girlfriends

1 Madonna

Tupac dated Madonna for a little over a year in 1993 after they were set up by pal Rosie Perez at the Soul Train Music Awards. Still, it wasn't until 2015 that Madonna confirmed their relationship in an interview with Howard Stern. "One time I was mad at [David Letterman] when I said the f-word a lot, but the rest of the time was good," Madonna recalled. "I was in a weird mood that day. I was dating Tupac Shakur at the time, and he had got me all riled up about life in general. So, when I went on the show, I was feeling very gangsta."

In 2017, TMZ published a letter that Tupac had written to Madonna while he was serving time at the Clinton Correctional Facility. In the heartbreaking note, which was dated Jan. 15, 1995, Tupac broke up with Madonna because of her race. "Can u understand that? For you to be seen with a black man wouldn't in any way jeopardize your career," the rapper wrote. "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."

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2 Whitney Houston

Image Source: Getty / Vince Bucci

In Bobby Brown's 2016 memoir Every Little Step, Whitney's ex-husband claimed that she had an affair with Tupac during their marriage. While Bobby didn't provide any more details, the couple were married from July 1992 to April 2007.

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3 Heather Hunter

Image Source: Getty / Hal Horowitz

Tupac and Heather first met after he contacted her to star in his video for "How Do You Want It" in 1996. Even though she was initially hesitant to take him up on the offer, Tupac inspired her to come back to LA from NYC. "It was amazing," she said in an interview with VladTV in 2016. "He was a really close and dear person to me. Just like anybody I hold close and dear, I respect him."

Heather eventually moved back to LA and the two developed a "spiritual" relationship. "It was everything," she recalled. "I think three or four months later he passed away."

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4 Kidada Jones

Image Source: Getty / John M. Heller

Tupac and Kidada's first meeting was at a club shortly before one of Tupac's trials in 1995. Kidada didn't speak to the rapper because he had previously dissed her father, Quincy, for marrying her white mother, Peggy Lipton. During their second meeting, Tupac apologized and she gave him her phone number, but by their third meeting, Tupac was already head over heels for her. "I love her," Tupac told his mom, Afeni, at the time. "She's going to be my wife, she's having my children."

Once Tupac served his time in jail and his marriage to Keisha was annulled, Tupac got a home with Kidada in Calabasas, CA. "Tupac was the love of my life," Kidada wrote in her father's 2001 autobiography. "He and I lived together for four months and then he was murdered in Las Vegas in 1996. It was the most horrible thing that ever happened to me."

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