Jada shared a strong bond with Tupac after meeting as students at the Baltimore School for the Arts in Maryland, and while their relationship was always platonic, Will admits he was a little resentful towards the Changes icon when they were first introduced by the actress.
Asked if he was ever jealous of Tupac, the 51 year old told New York radio show "The Breakfast Club", "F**k yeah. 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 explains he always felt Jada and Tupac's friendship may have turned romantic had he not already been involved with his "Fresh Prince of Bel-Air" co-star, who was in her early 20s when they first met in 1994.
"They never had a sexual relationship, but now they had come into that age where that was a possibility, and Jada was with me," he shared.
"She just loved him," Will added of how Jada's admiration for her best friend drove a wedge between the two men in her life.
"He was the image of perfection, but she was with the Fresh Prince, so it was, like, we were in the room together a couple times, (but) I couldn't speak to him. He wasn't going to speak to me if I wasn't going to speak to him."
"That was a huge regret of mine," he confessed. "I couldn't handle it."
Any chance Will may have had of mending his relationship with Tupac was cut short when the rapper was killed in 1996.
He and Jada went on to wed in 1997.