Will and his "Bad Boys for Life" co-star, Martin Lawrence, stopped by "The Breakfast Club" Monday, where co-host Charlamagne The God asked the former if he was "ever jealous of the love Jada had" for the slain rapper.
His response: "F--k yeah."
"And you know, that was in the early days. That was in the early days," he went on. "That was a big regret for me, too, 'cause I could never open up to interact with Pac... 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."
Jada and Tupac met at The Baltimore School for the Arts when they were both students. She's said in the past that they did once share a "disgusting kiss" and decided to keep their relationship platonic.
Even though he knows their connection was never romantic, Will still felt some type of way about it because he knew Jada held Tupac in such high regard.
"She just loved him," he explained. "He was the image of perfection, but she was with the Fresh Prince, so you know, it was like, I never could... We were in the room together a couple times, I couldn't speak to him. And you know, he wasn't going to speak to me if I wasn't going to speak to him."
Despite Jada's best effort to bring the guys together -- "Ya'll are so similar!" -- the two were never able to connect because Will simply "couldn't handle it."
"I was the soft rapper from Philly, and he was Pac," he recalled, reiterating that not forging a relationship with the West Coast hip-hop legend is still one of his biggest regrets. "I was deeply, deeply insecure. I wasn't man enough to handle that relationship."
Will met Jada on the set of "Fresh Prince of Bel-Air" in 1994. Tupac was shot dead in 1996, and the Smiths were married the following year.