Will Smith sat down for an interview with "The Breakfast Club" Monday where he spilled the tea that in his early days dating Jada, he was threatened by her friend Tupac Shakur's presence in her life.
"I was just deeply, deeply insecure and I just wasn't man enough to handle that relationship," Smith explained about his connection to Tupac.
Will explains the situation in more detail.
In his full statement, Will explained why he felt Tupac was a threat to the budding relationship with his now wife of 22 years.
"That was in the early days," Will explained. "That was a big regret for me too because I could never open up to interact with Pac 'cause we had a little bit of a thing, right, because you know, they [Tupac and Jada] 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."
Will went on to explain Tupac likely also held some resentment for him back in the day.
"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,'" he said.
How close were Jada and Tupac?
It's no wonder Will Smith felt intimidated by Tupac in the 90s.
The rapper was at the height of his career and was respected in the "gangster rap" community, while as Will points out, he was simply the "fresh prince" and a "soft rapper from Philly" at the time.
While rumors of an emotional or sexual relationship swirled around Jada and Tupac, she denies the two were ever intimate or romantically involved.
Yet, it makes sense that Will would be jealous, with Tupac including Jada in some of his poems and referring to her as his "heart in human form."
According to Jada, Tupac wasn't her type.
Yet, while Will was overcome with jealousy, Jada was simply unbothered and likely didn't get the hype.
While she became close friends with Tupac at the Baltimore School for the Arts in Maryland, she claims when it came to a romantic relationship, he simply wasn't her type.
"In high school, Pac was a little funny looking. Definitely from looking at him, wasn't necessarily the type of cat that I would even like, deal with," Jada said.
While she did admit to once trying to kiss the late rapper, she said she immediately realized the two would be better off as friends.
Will Smith is much less jealous now.
While Tupac is sadly not around to play a factor in Will and Jada's relationship anymore, it's likely the more mature Will would have befriended him today.
His approach to relationships has changed a lot in the last two decades as Will experienced what marriage life was like.
The two now work on battling their own insecurities to bring more individual happiness to their union as a couple.
"Her happiness is not my responsibility," Will famously said about his wife. "She should be happy and I should be happy individually. Then we come together and share our happiness. Giving someone a responsibility to make you happy when you can't do it for yourself is selfish."