Will Smith Says ‘Most Terrified’ He’s Ever Been Was on His ‘One and Only Date’ with Pepa of Salt-N-Pepa

Will Smith had one half of Salt-N-Pepe say, “Whatta Man,” briefly in the ’80s.

The actor/rapper, 55, invited the iconic hip-hop duo to his Class of ’88 podcast presented by Audible and Wondery to discuss their rise to rap superstardom in the ’80s — and reflect on how he was pretty smitten with Sandra “Pepa” Denton, 57, at the time.

In the episode, which aired earlier this fall, Smith and the rap star recalled the “one and only date” they went on together — and how “terrified” the Fresh Prince himself was during the experience.

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Smith said they went on a date “sometime in early ’88,” after he had been in love with the performer for some time. “I always had a thing for Sandy, but she was always dating someone else,” the Grammy winner said. “She was free now. We were both supposed to be in LA at the same time, so I’ll shoot.”

Since he only had one chance, the superstar explained that he felt he had to get it right. “This girl was special and I wanted to impress her, so I hired a white Mercedes convertible just because I needed some teeth,” he revealed. “My plan at the time was to take her to the Hollywood Hills, drive to Mulholland and all that, watch the sunset.”

DJ Jazzy Jeff and the Fresh Prince in the 80s.

David Corio/Michael Ochs Archive/Getty

Denton made it clear in the podcast that she remembers their date together, but one of the moves of the Oscar winner remained by far the most impressive. “I know exactly what happened,” she interjected. “We were outside and we saw a homeless man, and you gave the homeless man $100.”

The program “Push It!” the rapper continued, “I was like Alright and it was so nice. And then we went to the Hollywood sign.”

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Although Smith impressed the musician, he revealed that his mind was elsewhere at the time. “I was worried I was going to die,” he said King Richard the star admitted. “That was my concern when I was trying to spit my game, but I didn’t really have anything.”

Salt-N-Pepa.

Al Pereira/Getty Images/Michael Ochs Archive

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“I always faked like I had game. I didn’t really have game,” he added. “I was always in this full form, trying to give the craziest flavor of the game, but that was maybe the scariest I ever tried to shoot with Pep. And I didn’t believe I had the right shot.”

Although the star revealed that their brief relationship ended quickly after that night, he added that he, his former collaborator DJ Jazzy Jeff and Salt-N-Pepa have “always really hit it off”.

In celebration of hip-hop’s 50th anniversary earlier this year, the “Shoop” artists spoke with PEOPLE about their whirlwind career and what it’s been like to see the genre grow since they debuted.

DJ Jazzy Jeff and Fresh Prince. Michael Ochs Archive/Getty Will Smith and Jade Pinkett Smith’s Relationship Timeline

“For me, being in this genre and being so successful for so many years, it’s still an amazing emoji because we’re booked up and busy,” James said. “And I knew that Salt N Pepa would be successful, I just always believed in it. But I never thought we’d be in our fifties and still traveling and performing probably as much as we ever have.”

She added: “So it’s a testament to the power of culture and how much people accept and love it.”

The “Parents Just Don’t Understand” rapper also looked back to the early days of rap this year with the release of a track Class of ’88 — opening the podcast about his first impressions of music mogul Rick Rubin and his wild experiences on the road, among other anecdotes.

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Source: HIS Education