Will Smith was "deeply insecure" of his wife Jada Pinkett Smith's bond with Tupac.
The 'Girls' actress was close friends with the late music legend Tupac Shakur - whom she met when they both attended Baltimore School for the Arts - and whilst the pair stayed close up until Tupac's passing in 1996, Jada's husband Will has admitted it was hard for him to see her so close to another man.
Will - who married Jada in 1997 - insists he knows there was never anything romantic between Jada and Tupac, but said their friendly bond made it hard for him to speak to the hip hop icon.
He explained during an appearance on 'The Breakfast Club' with Charlamagne tha God: "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. 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 Will, 51, had many chances to form a friendship of his own with Tupac, he says he ego held him back.
He added: "It was like I never could even, we were in the room together a couple of times and I couldn't speak to him. You know, he wasn't going to speak to me if I wasn't going to speak to him."
Charlamagne then remarked that he thought Will and Tupac would have been kindred spirits who were close pals, and the 'Suicide Squad' star admitted he "regrets" not making more of an effort to befriend the late star.
He said: "Yeah that's what Jada would say all the time. 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. You know what I mean? I was deeply, deeply insecure, and I wasn't man enough to handle that relationship."