On the episode, 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, reports People magazine.

Smith said that they went on a date “sometime in early 1988” 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 were both going to be in Los Angeles 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 said, quotes by People. “My plan was then to take her around Hollywood Hills, drive up Mulholland and all that, watch the sunset.”

As per People, 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.”

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.”

"I was always faked like I had a game. I didn’t really have a game (sic)”, he added. “I was always in this full-on, trying to give the wildest flavour of having a 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.”