The two met at the Baltimore School of Arts and had a platonic relationship. Shakur even made a guest appearance on Pinkett-Smith’s sitcom, A Different World, before his death. And even though the pair never dated, Pinkett-Smith’s husband, Will Smith said he was jealous of their relationship, which kept him from getting close with Shakur.
Appearing on the Breakfast Club with Martin Lawrence to promote their movie — you can skip the 31:48 mark in the video below, Bad Boys for Life, Smith admitted his jealously of Shakur stemmed from his wife’s high regard of him. “She just loved him,” Smith said. “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.”
“That was a big regret for me, too, because I could never opened up to interact with Pac.”