Will Smith Admits He Wasn’t “Man Enough” To Handle Jada’s Relationship With Tupac

It takes a whole man to own up to his insecurities and Will Smith admits that he hadn't quite reached that level of maturity in the 90s'––around the time that his one-day wife was best friends with one of the most sought after rappers in the industry at that time.

It's true that men and women can be just friends, but friendship can become complicated when a jealous partner is involved and that's exactly the triangle of intimacy that Jada and Will found themselves at the start of their relationship. In a recent interview on The Breakfast Club, Will revealed that his relationship (or lack thereof) with Tupac was complicated, to say the least. He explained:

"Aww, f*ck yeah. Oh my God! Dude! And that was in the early days. And it was like—that was a big regret for me too because I could never open up to interact with Pac. We had a little bit of a thing because they grew up with each other. And they loved each other but they never had a sexual relationship. But they had come into that age where that was a possibility and then Jada was with me.

In the past, Jada has been transparent about her "complex relationship" with the rapper and says that although they were never physically intimate, they were "an anchor for each other," which ultimately created an atmosphere of tension in Tupac and Will's relationship; so much so, that the two rarely exchanged words. Will continued:

"So, Pac had a little thing on that. But she just loved him. He was the image of perfection but she was with the Fresh Prince. I never could–We were in the room together a couple times, I couldn't speak to him. And he wasn't gon' speak to me if I wasn't going to speak to him."

Will says that at this point in his life, he deeply regrets his inability to confront his insecurities and the missed opportunity to cultivate a relationship with the late-rapper. Despite Jada's attempts to strike up a bromance between her partner and her best friend, Will says that he was adamant about keeping his distance:

"[Jada's] like, 'I'm tellin' 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. I was deeply, deeply insecure and I wasn't man enough to handle that relationship."

More than two decades, two children, and a lifetime of love later, Will and Jada Pinkett Smith's relationship has proven that it can stand the test of both time and the tabloids but their love story didn't come without a few bumps in the road. But in the interview, Will noted that what happened on those romantic detours, Will says is none of our damn business. When asked why he and his wife will never divorce, Will had this to say:

"We've been wildly tested. We've tested each other. We've tested our commitment to our partnership. We've tested our commitment to our family. There's a certain amount of battery you have to subject each other to in order to know that you're really down. It ain't nothing I'm talking about on 'The Breakfast Club.'"

To watch the full interview, click below!

Will Smith & Martin Lawrence Talk 'Bad Boys' Trilogy, Growth, Regrets + Morewww.youtube.com

Featured image by Kevin Winter/Getty Images.