It's been 21 years since Tupac Shakur passed away, and to this day, there is still plenty of talk about the women who were in his life — more specifically, his love interests. We already know that Tupac was once married and that he and Jada Pinkett Smith had a "precious" relationship, but what about his girlfriends? From actresses to musicians to models, let's take a walk down memory lane and look back at all the women who were fortunate enough to date Tupac.
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."
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.
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."
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."
Tupac struck up a romance with Keisha after meeting at Capitol nightclub in NYC in the Summer of 1994. The two dated for a few months before eventually tying the knot on April 29, 1995, while Tupac was in jail for a previous sexual abuse incident. Sadly, their romance was short-lived, as their marriage was annulled in March 1996, five months after Tupac was released from prison.
"Things were getting very different once he got bail, and I felt like I wasn't needed anymore," Keisha said in a 1997 interview. "It wasn't a good feeling. OK, of course you don't know from being so young. But I just felt like, 'Wow, OK, it was over.' Like, 'OK, I don't need you anymore. I'm getting out.' That's it."
Still, Tupac and Keisha remained friends up until his tragic death on Sept. 13, 1996.
The details of Jara and Tupac's relationship are still a little hazy, but she briefly detailed what their romance was like in her autobiographyJumpOff: The Real Truth. "I would have to say my favorite was Tupac," she wrote. "He was so down to earth and he was a different person behind closed doors. What people don't know about Tupac is that he was a wonderful person and all that stuff in the public was not the real Tupac."
The two rappers first crossed paths in a recording studio in the '90s. After casually bumping into each other in various cities, Yo-Yo and Tupac became friends, and eventually, their relationship turned romantic. In an interview with WHUR-FM in August 2016, Yo-Yo revealed that she and Tupac dated until the day he passed away, even though they were more like brother and sister.
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