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Smith appeared on "The Breakfast Club" on Monday and told host Charlamagne Tha God that he "was deeply insecure" and not "man enough to handle that relationship."
Pinkett Smith discussed her "complex relationship" with Shakur during an interview with Whitney Houston's close friend Robyn Crawford in November.
Smith told "The Breakfast Club" that his jealousy of Shakur was a "huge regret."
"F--- yeah," Smith responded when radio host Charlamagne Tha God asked the actor if he was ever jealous of "the love Jada had for Tupac."
"And that was in the early days," Smith said. "That was a big regret for me. They grew up together but they never had a sexual relationship but now they had come into that age where that was a possibility, and Jada was with me."
Pinkett Smith and Shakur attended The Baltimore School of Arts together during the eighties and maintained a platonic friendship when Pinkett Smith met Smith on the set of "Fresh Prince of Bel-Air" in 1994.
Smith told "The Breakfast Club" that Jada used to tell him that he and Shakur were similar and would get along, but Smith said that he wasn't able to bring himself to open up to Shakur.
"I couldn't speak to him, and he wasn't going to speak to me if I wasn't going to speak to him," Smith said.
"He was the image of perfection, but she was with the Fresh Prince," he added, explaining that his jealousy grew from the high esteem Pinkett Smith held Shakur in.
"I was deeply insecure and I wasn't man enough to handle that relationship."
Pinkett Smith also discussed her relationship with Shakur during a 2019 Red Table Top interview with Whitney Houston's lifelong friend Robyn Crawford.
"We were anchors for each other," Pinkett Smith told Crawford. She stated that their friendship was "a complex relationship."
Pinkett Smith also told The Howard Stern Show in 2015 that she and Shakur had shared "the most disgusting kiss" after they tried becoming intimate. Shakur died in 1996 while Pinkett Smith and Smith married a year after.
Watch the full interview on "The Breakfast Club" below:
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