Will Smith Says He Was ‘Terrified’ On His Date With Pepa of Salt-N-Pepa

In the buzzing ’80s, Will Smith had a brief interlude with one-half of the iconic Salt-N-Pepa duo, and it’s a tale worth revisiting. On his ‘Class of ’88’ podcast, a platform presented by Audible and Wondery, Smith and the hip-hop legends delved into their journey to rap stardom during the vibrant ’80s.

Amidst the banter, Smith fondly reminisced about a memorable date with Sandra ‘Pepa’ Denton, back when he was a 55-year-old Fresh Prince.

According to Smith, their “one and only date” took place in early ’88, a momentous occasion given his long-standing crush on Pepa. Seizing the opportunity when both found themselves in L.A., Smith crafted a plan to impress.

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Yet, the podcast revealed an unexpected highlight of the evening. Pepa recalled encountering a homeless person during their escapade, and Smith handed over $100. A gesture that left a lasting impression on Pepa, making the Hollywood sign visit a memorable second act.

Smith, however, confessed to being more concerned about survival than showcasing charm. Admitting his lack of genuine game, he confessed, “I was always faking like I had game.” Despite his apprehensions, the brief fling fizzled out after that night. Nevertheless, Smith emphasized the enduring camaraderie between him, DJ Jazzy Jeff, and Salt-N-Pepa.

Fast forward to the 50th anniversary of hip-hop, Salt-N-Pepa reflected on their enduring success. Pepa marvelled at the genre’s growth, expressing disbelief at their continued relevance in their fifties.