Haunting First Date Story: Will Smith Recounts His Terrifying Encounter with Salt-N-Pepa Star.P6

Will Smith reminisces about his fear while on a date with Sandra “Pepa” Denton in the 80s and reveals his concern of dying.

In the ’80s, Will Smith had a date he would never forget. First rising as an actor and rapper, Smith charmed fans not only with his rhymes. But also with his attempt to win the heart of Sandra “Pepa” Denton from the iconic hip-hop duo Salt-N-Pepa.In a recent episode of his Class of ‘88 podcast, presented by Audible and Wondery, Smith reminisced with Denton about their brief romantic encounter. “Now she was single. We was both going to be in L.A. at the same time, so Imma shoot my shot.”

The episode revealed that Smith took Pepa on a date in early ’88. Wanting to make a lasting impression, he rented a white Mercedes convertible and planned a romantic drive through Hollywood Hills to watch the sunset.

On the podcast, Pepa Denton recalled their outing, highlighting one unforgettable moment. “We were out, and we saw a homeless person, and you gave the homeless person $100,” she recounted. Despite Smith’s effort to impress, he admitted his mind was preoccupied with fear.

“My concern was that I was going to get killed,” he confessed. “That was my concern when I was trying to spit my game, but I ain’t really have nothing.”

Unfortunately, the two ended their romantic connection after that night. Regardless, Will Smith emphasized that after the date, he and Salt-N-Pepa maintained a friendship. The podcast also delved into the early days of hip-hop. With Salt-N-Pepa reflecting on their enduring success. And the genre’s growth since their debut.

As they celebrate their impactful careers, the hip-hop pioneers continue to embrace and love the culture that has kept them booked and busy into their fifties.

Thea Felicity is part of ClutchPoints’ Entertainment team. She’s always in the loop with the hottest entertainment and celebrity news, glued to her socials all the time and has a knack for writing about a few sports too. Thea is also a pro science and technology writer.