Pinkett Smith and Shakur were close friends who attended the same performing arts school in Baltimore, before falling out shortly before Shakur’s murder in 1996.
Appearing on the US radio show The Breakfast Club, Smith said that he was envious of how close the pair were when he first began dating Pinkett Smith.
“F*** yeah,” he said. “That was in the early days. That was a big regret for me, too, because I could never open up to interact with Pac.
“They never had a sexual relationship, but now they had come into that age where that was a possibility, and Jada was with me.”
He continued, “She just loved him. 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.”
Pinkett Smith repeatedly tried to have the pair befriend one another, to no avail.
“That was a huge regret of mine,” he said. “I couldn’t handle it.”
In November, Pinkett Smith fought back tears during an interview with Whitney Houston’s close friend Robyn Crawford and referenced her own history with Shakur.
“It’s hard to love someone who has had a legacy at the level that she has had and then to lose them under tragic circumstances,” Pinkett Smith said. “Because I have a very similar situation.”