Did Jada Pinkett Smith Date Tupac Shakur?

Jada Pinkett Smith and the late Tupac Shakur’s were-they-weren’t-they relationship is one that still intrigues fans nearly three decades after his tragic death. On Sept. 20, a week after the 27th anniversary of the rapper’s death, Pinkett Smith took a trip down memory lane and posted an old clip of the two on Instagram ironically rapping along to her estranged husband Will Smith’s classic ’80s hit “Parents Just Don’t Understand.”

“Not in a million years would I have dreamed that the Fresh Prince and I would become, um, very acquainted,” she captioned the video, referring to her husband’s rap name. “Not in a million years did I imagine three lives, their fates, would be so intertwined. And… I never would have imagined that this video would become a tangible memory, of the last time Pac and I, were simply kids together. Pac and I lip syncing Parents Just Don’t Understand by Jazzy Jeff and the Fresh Prince during our Junior year in high school. Who would have thought?”

A few weeks later, on Oct. 12, the nature of Pinkett Smith and Shakur’s relationship piqued interest again after a revelation from the former’s episode on “All the Smoke with Matt Barnes & Stephen Jackson” surfaced online. In the interview preview, Pinkett Smith revealed details about the time that Shakur proposed to her when he was locked up at Rikers Island, which she talks about in her forthcoming “Worthy” memoir, out on Oct. 17. “When he asked me to get married . . . I knew at that time: A. he needed somebody to do time with him, which I was going to do anyway. You ain’t have to marry me to do time.”

Pinkett Smith also said she knew her late friend “needed a rock.” “Because of our friendship, because of everything we have been through together, he just wanted to feel that solidified foundation,” she added, also joking, “Because I promise you he would’ve married me and divorced me as soon as his ass left.”

The “A Different World” alum also added that, at that time, Shakur was starting to “shift” in a “good” way in his life: “I think that for him, he just felt like, ‘OK, if I can tether myself it’ll keep me on a trajectory.'”

Read on for everything else Pinkett Smith has revealed about her friendship with Shakur through the years.

Jada Pinkett Smith and Tupac Shakur’s Relationship, Explained

Pinkett Smith once recalled how she and Shakur first met at Maryland’s Baltimore School for the Arts, saying, “It was the first day and he came over to me and introduced himself.” She continued, “And in high school, Pac was a little funny looking. Definitely from looking at him, wasn’t necessarily the type of cat that I would even, like, deal with.”

According to the former “Red Table Talk” host, Shakur was “like a magnet” and quickly became one of her close friends. “He was like a brother,” she confessed. The actor, 52, reiterated those statements in an interview with Howard Stern, sharing how she even once tried to kiss the “Hail Mary” rapper, but discovered they were better off as just BFFs.

“You know, it’s so funny because now being older, I have more of an understanding of what that was between us. When you have two young people that have very strong feelings, but there was no physical chemistry between us at all, and it wasn’t even just for me — it was him too,” she clarified. “There was a time when I was like, ‘Just kiss me! Let’s just see how this goes,’ and when I tell you it had to be the most disgusting kiss for us both.”

Pinkett Smith told Stern she believed their awkward kiss was a sign from a “higher power” because “we might have killed each other because we were both so passionate and we love deeply.”

Unfortunately, according to Pinkett Smith, the pair’s friendship took a turn for the worse toward the end of Shakur’s life. “He felt as though I had changed,” she said. “I’d gone Hollywood. I’d gone soft. And looking back now, I totally understand where Pac was at the time. It was a mentality he started to come out of before he was murdered.”

Pinkett Smith said she felt Shakur was going in “a destructive direction”, which eventually led to them having a “hardcore” argument over their different lifestyles. The high school friends were not in contact before his untimely death on Sept. 13, 1996. “It definitely taught me a lesson, which is life is too short,” she told Stern. “Do not let disagreements stand in between you and people that you love.”

Pinkett Smith and Shakur’s relationship was portrayed in the 2017 film “All Eyez On Me,” with “Vampire Diaries” actor Kat Graham playing the former. Shortly after the release, Pinkett Smith spoke out about the events she felt were misrepresented in the movie, writing on X (formerly Twitter), “Forgive me … my relationship to Pac is too precious to me for the scenes in All Eyez On Me to stand as truth. . . . The reimagining of my relationship to Pac has been deeply hurtful.”

The “Scream 2” actor pointedly took issue with the film’s portrayal of the poems Shakur wrote for her, which Pinkett Smith says she never knew existed until she read his 1999 poetry book, “The Rose That Grew From Concrete.” She ended her series of tweets by stating that her late friend will be “cradled in [her] heart for eternity.”