Entertainment Movies Will Smith Says He Was Jealous of Jada Pinkett Smith's Love for Tupac: 'I Couldn't Handle It' Will Smith opened up about the insecurity he felt toward wife Jada Pinkett Smith's love for her friend Tupac Shakur By Alexia Fernández Published on January 13, 2020 08:30 PM Share Tweet Pin Email Will Smith is opening up about his feelings toward his wife Jada Pinkett Smith‘s deep connection to rapper Tupac Shakur. The Bad Boys for Life actor, 50, spoke to Charlamagne tha God with his costar Martin Lawrence while promoting their new film when he was asked if he had ever been jealous of the love Jada had for the late rapper. “Oh f— yeah. Oh my God,” Will said. “That was in the early days and it was like, that was a big regret for me, too, because I could never open up to interact with Pac.” He explained he and Tupac “had a little bit of a thing” over their love for Jada, who was childhood friends with Shakur. “You know, they grew up together and they loved each other but they never had a sexual relationship but they had come into that age where it was a possibility and then Jada was with me,” Will said. “Pac had a little thing on that but she just loved him, like he was the image of perfection, but she was with the Fresh Prince, you know? So, I never could, we were in the room together a couple of times, I couldn’t speak to him, and he wasn’t going to speak to me if I wasn’t going to speak to him.” Charlamagne expressed surprise, saying, “Really? It seems like y’all would have so much in common.” “That’s what Jada would say all the time: ‘I’m telling you, y’all are so similar, you would love him,'” Will recounted. “And I just never… that was a huge regret of mine, I couldn’t handle it.” “I was the soft rapper from Philly and he was Pac,” Will continued. Neilson Barnard/Getty Images; Raymond Boyd/Getty Images; Frazer Harrison/Getty Images At the time, he was also lacking confidence in himself, the actor explained. “I was deeply, deeply insecure and I wasn’t man enough to handle that relationship,” Will added. Jada has been open about her friendship with Shakur, who was killed in a drive-by shooting in September 1996. He was 25. The actress and Shakur met on the first day of high school in Baltimore and grew increasingly close until Jada walked away from their friendship when she felt his life was getting too dangerous. In November, Jada spoke to Robyn Crawford about her relationship with Whitney Houston, which Crawford detailed in her book A Song for You: My Life with Whitney Houston. Jada Pinkett Smith Breaks Down in Tears Talking About Close Friend Tupac Shakur’s Tragic Death “It was so healing for me in so many different ways,” Jada said of the book. “It’s hard to live with someone who has had a legacy at the level she has had and then to lose them under tragic circumstances. I have a very similar situation.” She continued, “I understood because of the complex relationship I’ve had with Pac. In those moments of his, ‘Who’s that?!’ knowing damn well there ain’t nothing like that between us.” “Him feeling like, ‘You’re the only stability I got. I can’t afford for you to put that attention elsewhere. I need that stability.’ So for him, it was… we were an anchor for each other. So any time he felt like that anchor was threatened… Oh my God,” she continued of her friendship with Shakur.