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

The actor/rapper and Sandra "Pepa" Denton reminisced about the time they went out on 'Class of '88' podcast

Will Smith had one half of Salt-N-Pepa saying, “Whatta Man,” for a brief period in the ‘80s.

The actor/rapper, 55, invited the iconic hip-hop duo on his Class of ‘88 podcast presented by Audible and Wondery for a chat about their ascension towards rap superstardom in the ‘80s — and to reflect on how he was rather smitten with Sandra "Pepa" Denton, 57, at the time.

On the episode, which was released earlier this fall, Smith and the rap star reminisced about the “one and only date” they went on together — and how “terrified” the Fresh Prince himself was throughout the experience.

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Smith said that they went on a date “sometime in early ‘88” after he had been crushing on the performer for quite some time. “I always had a thing for Sandy, but she was always dating somebody else,” the Grammy winner shared. “Now she was single. We was both going to be in L.A. at the same time, so Imma shoot my shot.”

Since he only had one chance, the superstar explained that he felt he had to do it right. “This girl was special and I wanted to impress her, so I rented a white Mercedes convertible just because I needed to floss a little bit,” he revealed. “My plan was then to take her around Hollywood Hills, drive up Mulholland and all that, watch the sunset.”

Denton made it clear on the podcast that she remembered their outing together, too, but one of the Oscar winner’s moves was by far the most memorable. “I know exactly what happened,” she interjected. “We were out and we saw a homeless person and you gave the homeless person $100.”

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

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While Smith had the musician impressed, he revealed that his mind was somewhere else at the time. “My concern was that I was going to get killed,” the King Richard star admitted. “That was my concern when I was trying to spit my game, but I ain’t really have nothing.”

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"I was always faked like I had game. I didn’t really have game,” he added. “I was always in this full-on, trying to give the wildest flavor of having game, but that might have been the most terrified I had ever been trying to shoot my shot with Pepa. And I didn’t believe I had a real shot.”

Although the star revealed that their brief fling quickly petered out after that night, he added that he, his former collaborator DJ Jazzy Jeff and Salt-N-Pepa “always really got along."

Upon the 50th anniversary of hip-hop earlier this year, the "Shoop" artists spoke to PEOPLE about their whirlwind career and what it’s been like seeing the genre grow since they debuted.

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“For me being in this genre and so successful for so many years, it is still mind blown emoji, because we are booked and busy,” James shared. “And I knew Salt N Pepa were going to be a success, I just always believed that. But I never thought in my mind that we would be in our fifties and still traveling and performing probably just as much as we ever did.”

She added, “So that's a testament to the power of the culture and how much people embrace it and love it.”

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

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