Will Smith has admitted being “deeply insecure” about wife Jada Pinkett Smith’s relationship with the late rapper Tupac Shakur.

Pinkett Smith met Shakur in high school and they remained close friends until his death in 1996.

Hollywood star Smith, who began his career as a rapper, met his future wife in 1994 on the set of his TV show The Fresh Prince Of Bel-Air.

Will Smith
Will Smith has revealed his regrets over not befriending the rapper Tupac Shakur (Isabel Infantes/PA)

The two started dating the following year but Smith, 51, has now admitted he struggled to befriend Shakur.

Speaking on The Breakfast Club radio show, he said: “I could never open up to interact with Pac. 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.”

Smith, who has two children with Pinkett Smith, said he and Shakur, who was shot dead at the age of 25, would not speak to each other even if they were in the same room.

He told how it was a “huge regret” the two never became friends.

“I couldn’t handle it,” he said. “I was the soft rapper from Philly and he was Pac. You know what I mean? I was deeply, deeply insecure and I wasn’t man enough to handle that relationship.”

Pinkett Smith has previously spoken of her relationship with Shakur, who she called an “icon”.

Speaking on her Red Table Talk show, she said: “I’ve had a lot of loss. So many of my close friends gone. They didn’t make it to 30. They didn’t make it past 25.

“A lot of people talk about my relationship with Pac and figure that out. That was a huge loss in my life.”