Will Smith Confesses He Was Jealous About Jada Pinkett’s Relationship With Tupac

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Will Smith, 51, understands the close relationship his wife Jada Pinkett Smith, 48, had with the late Tupac and in his early days of dating her, he was jealous. The former Fresh Prince of Bel-Air star sat down for an interview on The Breakfast Club on Jan. 13 and talked about the concerns he had over the love his now spouse and the rapper had back then and how it even caused some tension that he regrets.

“Oh F**k yeah,” Will responded when host Charlamagne tha God asked if he was jealous of Jada and Tupac on the radio show. “That was in the early days. That was a big regret for me too because I could never open up to interact with Pac ’cause we had a little bit of a thing, right, because you know, they [Tupac and Jada] grew up together and they loved each other but they never had a sexual relationship but they had come into that age where now that was a possibility and then Jada was with me. So, 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”.

Although he was the one Jada was dating, Will went on to admit that he could never quite let the tension for Pac go. “We were in a room together a couple times and I couldn’t speak to him and you know, he wasn’t gonna speak to me if I wasn’t gonna speak to him.” Charlamagne then pointed out that Will had a lot in common with Tupac, and he agreed, saying Jada would tell him that all the time. “She was like, ‘I’m telling you, you all are so similar, you’ll love him’ and I just never…you know, that was a huge regret of mine. I just couldn’t handle it. I was this soft rapper from Philly and he was this Pac, you know what I mean?”

“I was just deeply, deeply insecure and I just wasn’t man enough to handle that relationship,” Will concluded.

Will’s admissions may seem quite shocking to some since he and Jada have become one of the most inspirational couples in Hollywood. The lovebirds first met in 1994 when the actress auditioned to be on The Fresh Prince of Bel-Air. Although she didn’t get the part, she became friends with Will and they started dating in 1995. They went on to marry at the end of 1997 and share two children, including son Jaden, 21, and daughter Willow, 19. Jada is also the stepmother of Will’s oldest son Trey, 27, who he had during a previous marriage. Tupac died one year after Will and Jada started dating when he was murdered in Sept. 1996 at the age of 25.