He did not shy away from admitting his insecurities about their close bond and his regret of not getting to know the slain rapper better as a result.
The award-winning actor and rapper touched on the topic when he passed by Power 105’s The Breakfast Club with Martin Lawrence as part of the promo tour for the yet-to-be-released Bad Boys for Life movie.
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Asked by host Charlamagne tha God if he was ever jealous of the love Jada had for the Changes rapper, the 51-year-old replied: “F*ck yeah.”
“That was in the early days,” he added. “That was a big regret for me, too, because I could never open up to interact with Pac.”
Jada and Tupac grew a special bond when they met at The Baltimore School for the Arts where they were enrolled as students during their teenage years. Their friendship blossomed onwards and both were still in contact even when Smith and Jada were dating.
“They never had a sexual relationship, but now they had come into that age where that was a possibility, and Jada was with me, so Pac had a little thing on that,” he said.
Though Jada, in a 2015 interview with Howard Stern claimed she and Tupac were never physically attracted to each other, she revealed an instance where they kissed and described it as the “most disgusting kiss” for both of them.
“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 said.
“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. The only way I can put it is, the higher power just did not want that.”
“She just loved him,” Smith recalled. “He was the image of perfection, but she was with the ‘Fresh Prince,’ So it was, like, we were in the room together a couple times, I couldn’t speak to him. He wasn’t going to speak to me if I wasn’t going to speak to him.”
Charlamagne chimed in surprised about the two not getting along because he felt they had so much in common. Smith concurred and even revealed Jada said same and tried convincing him to loosen up.
“That was a huge regret of mine, I couldn’t handle it. I was the soft rapper from Philly and he was Pac,” he admitted.
“I was deeply, deeply insecure and I wasn’t man enough to handle that relationship.”