Over the years, there have been speculations and rumors about who the love of Tupac Shakur’s life was. But who held that title? Depending on who you ask, that position belongs to Jada Pinkett Smith. But according to rapper Yo-Yo, she had the crown. September 13th in the year 1996 was one of Hip-Hop’s darkest days. Legendary rapper Tupac Shakur succumbed to fatal injuries stemming from a violent incident. Though only 25, his impact was undeniable. Heartbreak rang loud and firm around the globe upon hearing the news that the “California Love” artist was no longer with us. Leaving behind family, close friends, and adoring fans, there were also women who closely “knew” ‘Pac that would no longer feel his presence.
Ever the ladies man, the chart-topping, Harlem-born rapper was romantically linked to some of Hollywood’s biggest names. Yet, seemingly, very “caring” and “loving” are the words that tend to describe the rapper.
One of the women that had a seemingly incredible affection for Tupac Shakur was late TLC group member Lisa “Left-eye” Lopes. Their attraction and chemistry were so strong that it caused many issues in left-eye’s relationship with her then-boyfriend, Andre Rison. A docu-series on Lifetime called Hopelessly in Love gives accounts from various sources that detail Left-Eye’s love for Tupac and vice versa. And although it was evident that there were deep feelings between the two artists, many confirmed in the documentary that they never crossed the line intimately.
Songwriter Delray Richardson gave an account in a conversation with The Art Of Dialogue where he recalled the “Waterfalls” rapper ready to attack another woman out of jealousy. Richardson claimed that one night while at a club with Tupac in West Hollywood, Left-Eye appeared and spotted the rapper speaking with another woman. According to Richardson, Left-eye then confronted them as she was upset to see Tupac with a woman that was not her, although they were not together. While their relationship never went beyond a friendship, they are said to have remained close until his passing.
Another woman that many assumed that Tupac Shakur was dating was Rosie Perez. The Do The Right Thing actress and Tupac were photographed together holding hands on the red carpet of the Soul Train Awards in 1993. Rumors swiftly began to circulate that Perez was Shakur’s new boo. However, the actress has since debunked those rumors and stated that Shakur was only a good friend that stepped up when her date stood her up! While Perez may not have been Tupac’s girl, she is the reason for one of his relationships.
The “Material Girl ” herself, Madonna, was also in attendance at the Soul Train Awards. While she was a co-host on The View, Rosie Perez confirmed that she “hooked that up.” Madonna would then later confirm that she dated Tupac during some interviews. Years later, a letter that Tupac wrote to Madonna in 1995 while he was incarcerated surfaced online explaining their break-up.
Tupac Shakur and Janet Jackson’s onscreen chemistry on Poetic Justice left many to believe that they could perhaps be a couple in real life. However, this was not the case. Shakur also claimed in a past interview that in order for him to participate in an intended love scene for the film, he would have had to take an AIDs test. It was later determined to be a publicity stunt by John Singleton to bring awareness to the film.
Perhaps the most talked-about connection Tupac has shared with a woman is Jada Pinkett-Smith. The actress has often spoken in-depth about their relationship. And although many have speculated they were an item, Jada Pinkett-Smith assures that it was nothing more than a sincere friendship. There was a time, the actress admits, where they attempted to see if there was chemistry. But after a failed kiss, they realized there was no spark.
The connection between Tupac and Jada Pinkett-Smith was so deep that it admittedly made Will Smith insecure when they encountered one another. In his newly released memoir, the actor revealed that he could never build any type of friendship with Tupac due to his “immaturity.” Yet, shockingly, daughter Willow wrote a letter to the late rapper when she was younger, claiming to know that her mother “misses” him and begging him to “come back” to make her mother “happy.”
Other women have been thought to be attached to Tupac or have been involved with the rapper, from Jasmine Guy to Monie Love. But west coast rapper Yo-Yo, who was close with Tupac and had relations with the rapper, states that she was Tupac’s true love, not Jada Pinkett-Smith. Laughing throughout her statement and claiming to be joking, Yo-Yo clarified that Tupac did have a love for not just Jada but women in general. “He was a sweetheart,” the rapper said. “He was a romantic person. I mean, anybody he dealt with he loved.”