Why Nothing Romantic Ever Happened Between Jada Pinkett Smith & Tupac Shakur

Jada Pinkett Smith and Tupac Shakur shared a deeply intimate friendship that began as teenagers attending the Baltimore School for the Arts. Their bond transcended mere friendship and bordered on soul connection, as both understood each other's struggles and tumultuous childhoods. Shakur expressed his affection for Jada on several occasions, stating in one 1995 interview, "Jada is my heart. She will be my friend for my whole life." And that's all they ever were: just friends. 

While it's been decades since Shakur was murdered, the "Red Table Talk" host has continuously praised her late friend in interviews and on social media multiple times. In 2021, she honored Shakur on what would have been his 50th birthday via Instagram, sharing one of the handwritten poems he wrote with the caption, "As we prepare to celebrate his legacy ... let's remember him for that which we loved most ... his way with words." The mom of two also told Rolling Out in October 2023 that Shakur was her soulmate. 

Despite years' worth of dating rumors between Pinkett Smith and Shakur and their affectionate words towards one another, Pinkett Smith would begin dating now-husband Will Smith in 1995. She and Shakur maintained more of a familial bond after realizing, in the most awkward way, that their feelings for one another were not romantic.

Jada Pinkett Smith and Tupac Shakur may have been the best of friends, but there was a time when they attempted to see if there was any spark between them by sharing a quick kiss. During a 2015 chat with Howard Stern, Pinkett Smith detailed the moment, sharing, "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." She would later admit during that chat that their lack of chemistry was likely for the best, as their friendship could be explosive at times.

Years later, in her October 2023 memoir, "Worthy," the author revisited the kiss, which she once again seemed repulsed by, writing, "The kiss lasted a few seconds before we both pulled away in mutual disgust. It felt wrong ... It was literally like a sister and brother trying to make out." After this kiss, Shakur tried once more to explore something beyond friendship when he proposed to Pinkett Smith from behind bars while serving a jail sentence for an alleged sexual assault against a woman visiting his hotel room. Pinkett Smith declined the proposal, though his legal troubles may have played a role in the "Set It Off" star distancing herself from Shakur.

Jada Pinkett Smith and Tupac Shakur chose to remain friends even after their failed attempt at a relationship. However, even their friendship took a hit as Shakur went on a separate path from her. When speaking with Howard Stern, Pinkett Smith shared that she expressed her concerns with Shakur, explaining, "I just wasn't in agreement with the direction that he was taking, and I told him that, you know, it was a destructive direction. A very scary direction. And he felt as though I had changed. I'd gone Hollywood. I'd gone soft." Unfortunately, they did not reconcile by the time Shakur died in a Las Vegas shooting in September 1996.

Pinkett Smith went through a period of depression after his death, mostly due to their estrangement at the time. The actor is confident that she knew Shakur was aware of her feelings towards him even with their distance. Though they never made their relationship official, the love between them remained.