Will Smith was “terrified” during a date with Salt-N-Pepa star Sandra “Pepa” Denton.
The Men in Black star asked the musician out in early 1988. He pulled out all the stops to impress her by renting a white Mercedes convertible, planning a drive around Los Angeles and ending with a stop in the Hollywood Hills to watch the sunset.
However, Smith admits nerves almost got the better of him.
“[It was] sometime in early ‘88 … I always had a thing for Sandy, but she was always dating somebody else,” he explained during an appearance on his “Class of ‘88” podcast alongside Salt-N-Pepa. “Now she was single. We were both going to be in L.A. at the same time, so I’mma shoot my shot. … 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. My plan was then to take her around Hollywood Hills, drive up Mulholland and watch the sunset.”
However, Denton said there was one part of the date that impressed her the most: she was pleased to see Smith show kindness to a homeless person.
“I know exactly what happened,” she explained. “We were out and we saw a homeless person, and you gave the homeless person $100. I was, like, OK — and it was so nice. And then we went to the Hollywood sign.”
“My concern was that I was going to get killed,” Smith added. “That was my concern when I was trying to spit my game, but I ain’t really have nothing … I 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.”
However, the romance didn’t last as it fizzled out shortly after their first date. Smith insisted the pair “always really got along.”
He went on to wed Jada Pinkett almost a decade later in 1997; Denton was married to rapper Treach from 1999 to 2001.
