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During an interview, Will Smith recently revealed that he was “deeply insecure” regarding his wife, Jada Pinkett Smith’s relationship with the late rapper Tupac Shakur.

When Smith was asked if he were ever jealous of the love that his wife had for the “Picture Me Rollin'” rapper, and he responded “yeah!” after letting out an F-bomb.

However, the actor said that he regrets not cultivating a friendship with Shakur. “That was a big regret for me too because I could never open up to interact with Pac,” Smith said.

“You know because we had a little bit of a thing. You know, they grew up together and they loved each other, but they never had a sexual relationship.”

Pinkett Smith and Shakur met while they were both attending high school at Baltimore School for the Arts in Maryland, and the two became close friends prior to Pinkett Smith meeting Will Smith.

“They had come into that age where now that was a possibility and then Jada was with me,” recalled Will.

“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.”

“It was like I never could even, we were in the room together a couple of times. I couldn’t speak to him,” Will continued. “You know, he wasn’t going to speak to me if I wasn’t going to speak to him.”

The interviewer postulated that Will Smith that he and Shakur probably would have a lot in common. “That’s what Jada would say all the time,” said Will. “Like, ‘I’m telling you, y’all are so similar you will love him,’ 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.”

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

In the past, Pinkett Smith has been vocal regarding her friendship with Shakur. “He was one of my best friends,” she said. “He was like a brother. It was beyond friendship for us, as far as just, it’s really difficult to explain because the type of relationship we had, you only get that once in a lifetime. He was like a brother-father figure to me. Very protective. We took really good care of each other, the best that we could. We gave each other a lot.”

Will Smith talked about Jada’s relationship with Shakur while promoting his new movie Bad Boys for Life with Martin Lawrence.

Glennisha Morgan is a Detroit-bred multimedia journalist and writer. She writes about intersectionality, hip-hop, pop culture, queer issues, race, feminism, and her truth. Follow her on Twitter @GlennishaMorgan.