Will Smith Says He Was Terrified On His ‘One and Only Date’ with Pepa of Salt-N-Pepa

In a recent episode of his Class of ’88 podcast, hosted by Audible and Wondery, Will Smith had a candid conversation with the iconic hip-hop duo. The discussion not only explored their journey to rap superstardom in the ’80s but also uncovered some personal memories. Among these was Smith’s admission of being quite taken with Sandra “Pepa” Denton during that period.

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The episode, released earlier this fall, featured insights into their “one and only date” and highlighted Smith’s humorous recollection of feeling “terrified” throughout the experience.

Smith reminisced about their date, revealing that it took place “sometime in early ’88” after he had harbored a crush on the performer for quite some time. The Grammy winner expressed, “I always had a thing for Sandy, but she was always dating somebody else. Now she was single. We was both going to be in L.A. at the same time, so Imma shoot my shot.”

During the date, Smith had Denton impressed, but he candidly shared that his mind was preoccupied with concerns about personal safety. “My concern was that I was going to get killed,” confessed the Will.

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“My concern was that I was going to get killed,” Smith added. “That was my concern when I was trying to spit my game, but I ain’t really have nothing … I always faked like I had game. I didn’t really have game. I was always in this full-on, trying to give the wildest flavor of having game. But that might have been the most terrified I had ever been, trying to shoot my shot with Pepa. And I didn’t believe I had a real shot.”

 Despite the initial sparks, the romance between Smith and Denton didn’t last, with Smith maintaining that the two “always really got along.”