Back in time: Will Smith was ‘most terrified’ on his ‘one and only date’ with Pepa of Salt-N-Pepa

Hollywood star Will Smith invited the iconic hip-hop duo Salt-N-Pepa on his Class of 1988 podcast for a chat about their ascension towards rap superstardom in the 1980s, and to reflect upon how he was rather smitten with Sandra “Pepa” Denton, 57, at the time.

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.

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.”

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. “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”.