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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.

https://podcasts.apple.com/us/podcast/the-showstoppers/id1708275587?i=1000631906912

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.

Salt-N-Pepa.

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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