Will Smith’s Throwback: A 1988 Date with Salt-N-Pepa’s Pepa (Listen)

Fresh Prince Recalls His "Most Terrified" Moment Trying to Impress the Hip-Hop Icon
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In a nostalgic episode of his Class of ’88 podcast, Will Smith reminisced about a memorable date with Sandra “Pepa” Denton from the iconic hip-hop duo Salt-N-Pepa. The actor/rapper revealed the details of their “one and only date,” which took place in early ’88 when he finally had the chance to impress the rap superstar.


Smith confessed to having a longstanding crush on Pepa but had previously refrained from expressing his feelings as she was always in a relationship. Seizing the opportunity when both would be in L.A., Smith rented a white Mercedes convertible and planned a romantic evening driving around Hollywood Hills, watching the sunset.


During the podcast, Pepa remembered the date vividly, highlighting one standout moment. She recalled encountering a homeless person during their outing, and Smith spontaneously gave the individual $100. Despite Smith’s attempt to impress her, he admitted that his main concern was his own safety, confessing he was “the most terrified” while trying to make a move on Pepa.

DJ Jazzy Jeff and the Fresh Prince.

While their brief fling didn’t lead to a lasting romance, Smith shared that he, DJ Jazzy Jeff, and Salt-N-Pepa continued to have a great relationship over the years. The podcast episode provided fans with a charming glimpse into the Fresh Prince’s past, revealing a vulnerable and humorous side to his pursuit of love.

December 29, 2023

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