Will Smith Says ‘One and Only Date’ With Pepa Had Him the ‘Most Terrified’ He’s Ever Been

The date took place during the late 1980s.

Will Smith was crushing on one half of Salt-N-Pepa during the late 1980s, and the one date they went on with her had him terrified over the possible outcomes.

During an appearance on the “Class of ‘88” podcast, the rapper-turned-actor reflected about being smitten with Sandra “Pepa” Denton back in the day. During the episode, which was released earlier this fall, he described the “one and only date” they went on together and how “terrified” he was during the experience.

“I always had a thing for Sandy, but she was always dating somebody else,” Smith said. “Now she was single. We was both going to be in L.A. at the same time, so Imma shoot my shot.”

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Smith added that he felt he had to do it correctly if he were to receive a second date. 

“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.”

Pepa, who was also on the pod, pointed out one of the more memorable parts of the date: “I know exactly what happened,” she interjected. “We were out and we saw a homeless person and you gave the homeless person $100. I was like ‘okay’ and it was so nice. And then we went to the Hollywood sign.”

Smith said he was worried about being rejected. “My concern was that I was going to get killed,” he 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 game. I didn’t really have game. 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.” 

Listen to the full podcast episode here.

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