Will Smith has been dealing with feeling jealous over his wife’s relationships with over men since they became a couple.
In the early days of his relationship with now wife Jada Pinkett Smith, the Fresh Prince star was left feeling “deeply insecure” over he love for a childhood friend.
Will’s worrying feelings were down to her ‘complex’ relationship with late rapper Tupac Shakur – which has left him with one major regret.
Jada and Tupac both attended the same high school in Baltimore, becoming instant friends, but they went on to have a strained relatinship.
They were still very close pals and were in constant contact when Jade hooked up with Will, but they had a major falling out just before the rapper was fatally shot in September 1996.
Will confessed he could not stand that Tupac was the “image of perfection” in Jada’s eyes and refused to speak to him when they were in the same room.
As an up and coming rapper himself, Will developed an unspoken rivalry with Tupac despite Jada’s efforts to help them bond.
When asked on Power 105’s The Breakfast Club in January this year if he felt jealous over Jada’s ‘love’ for Tupac, Will strongly cried: “F*** yeah.”
While admitting he was “jealous” of their relationship, Will did reveal that he regretted not getting to know his wife’s friend better.
“That was in the early days. That was a big regret for me, too, because I could never open up to interact with Pac.”
Will and Jada met on the set of The Fresh Prince of Bel-Air in 1994 before marrying three years later.
The Hollywood actor was adamant that Tupac and Jada never had a sexual relationship, but things got awkward when he first got together with her.
“We had a little bit of a thing. They grew up together and loved each other but never had a sexual relationship,” explained Will.
“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.”
Jada thought of Tupac like her “brother” when they went to Baltimore High School of the Performing Arts together.
“She just loved him. He was the image of perfection,” said Will, who explained what brought about their differences.
“But she was with the ‘Fresh Prince,’ so it was, like, we were in the room together a couple times, I couldn’t speak to him.
“He wasn’t going to speak to me if I wasn’t going to speak to him.”
Jada tried to convince Will to ‘loosen up’ around Tupac in a bid to make the men in her life be civil around each other.
But they never spoke before Tupac’s untimely death – and Will confessed that he wished that he had been different in the rapper’s presence.
“That was a huge regret of mine, I couldn’t handle it. I was the soft rapper from Philly and he was Pac,” admitted Will.
“I was deeply, deeply insecure and I wasn’t man enough to handle that relationship.”
Jada has always been very honest and open about her close friendship with Tupac – admitting they once shared a kiss.
But she claimed they were not ‘physically attracted’ to one another and it was the “most disgusting kiss” they had both ever had.
“When you have two young people that have very strong feelings, but there was no physical chemistry between us at all, and it wasn’t even just for me, It was him too,” she told Howard Stern in 2015.
“There was a time when I was like, ‘Just kiss me! Let’s just see how this goes.
“And when I tell you it had to be the most disgusting kiss for us both. The only way I can put it is, the higher power just did not want that.”
In the same interview, Jada revealed described how she got into a “hardcore” fight with Tupac before he died.
The legendary rapper was killed in a drive-by shooting in Las Vegas during 1996 at the age of just 25-years-old.
“There’s not a day that goes by that I don’t think about Pac. I think about him every single day,” she said of her high school friend.
Jada also emotionally admitted it is “hard to love someone who has a legacy” during a powerful discussion in November 2019.
While recalling her complex relationship with Tupac with Robyn Crawford on her chat show Red Table Talk, Jada broke down in floods of tears.
The pair spoke about the struggle of loving someone in the spotlight following the release of Robyn’s book A Song For You which details her love affair with Whitney Houston.
“When you said [the book is] a love letter to Whitney, that resonated as so powerful,” Jada told her guest.
“It was so healing for me in so many different ways. It’s hard to live 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.”
Jada went on to explain that she and Tupac acted as “anchors” for each other when they found fame at an early age.
“Him feeling like, ‘You’re the only stability I got, I can’t afford for you to put that attention elsewhere,’” Jada said of her pal Tupac.
“For him, it was, we were an anchor for each other. Anytime he felt like that anchor was threatened, oh my God,'” she added.
Jada and Tupac bickered before his tragic death over her fears that he was heading down a destructive path.
They were still not on speaking terms when Tupac was killed in Las Vegas in 1996 – meaning Jada sadly never got to make ammends.