Will Smith Admits He Was 'Deeply Insecure' About Jada Pinkett Smith's Relationship With Tupac Shakur

Will Smith isn’t afraid to open up when it comes to discussing his marriage.

During a recent appearance on The Breakfast Club to promote his upcoming film Bad Boys For Life, the 51-year-old actor revealed he was very jealous of the super close relationship his wife Jada Pinkett Smith had with the late Tupac Shakur.

“Oh f**k yeah,” said the Academy Award winner when host Charlemagne the God posed the question about his animosity towards the California rapper.

Will went on to explain how Jada and Pac’s long history kept the men from ever becoming real friends:

“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.”

For those who may not know, the 48-year-old Red Table Talk host met the hip-hop legend when they were young classmates at the Baltimore School for the Arts in Maryland. The two were instant friends and remained in contact well after their school days were behind them.

Fast-forward several years later to when the starlet coupled up with Smith. As the Gemini Man actor tells it, Shakur’s continued presence in their lives filled him with doubt:

“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 the guys had many chances to create a friendship, Will admits his ego held him back:

“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.”

He also added Jada would repeatedly encourage him to break the ice and brought up all the things they have in common, but he never listened:

“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.”

Sigh. Love is complicated!

Some bonds go so far back in time they just can’t be replaced with anything or anyone else. Nor should they be!

With two beautiful children, Jaden Smith and Willow Smith, and years of happy memories between them, the pair’s union certainly survived whatever jealousy that threatened to derail it before. Despite his regrets, the star seems to have learned a valuable lesson about pride he’ll most likely keep forever.

WATCH him explain it all in his own words (below), starting at the 31-minute mark!