In a new excerpt from Smith’s podcast Class of ’88 that features the star talking with Salt-N-Pepa, Denton — who toured with the Fresh Princeand his partner DJ Jazzy Jeff during the early days of their music career — shared that she went on a single date with Smith, and was intrigued by him, but denied his advances because she felt he was far too “nice.”
“Okay, you were very nice,” she began recalling the date began with a drive in L.A. “This was the date you won and beat us out. You was so happy. You was like let’s go celebrate,” she said, referencing Smith’s first-ever Grammy win in 1989 where he and Jeff beat out Salt-N-Pepa and LL COOL J, who were also nominated in the rap category.
“Then we were out and you saw a homeless person. You gave the homeless person $100. And it was so nice. Then, we went to the Hollywood sign,” she continued, as Smith recalled Pepa was on a break from her ex, Treach.
“I think you and Treach had been broke up for a minute. So, in my mind when I was like trying to spit my game but I ain’t really have nothing. Cuz my concern was I was gonna get killed,” said Smith. It was a sentiment Salt agreed “was a legit concern,” a response that made everyone assembled crack up laughing.
Soon after catching wind of the clip, Treach himself took to socials where he addressed the situation by poking fun at the Chris Rock-Smith slapping incident. “”KEEP MY NAME CONCERNING MY EX-BITCH OUT YO FUCKING MOUTH”!! [laughing emoji],” he captioned a post in which he reshared a headline about the story.
Denton’s comments echo a 2009 interview with Global Grind where she elaborated on her regret.
“I thought Will was really cute, and we would hang out a lot on the road. He liked to take care of me and never let me spend a dime. He was that kind of guy, real generous,” said Pepa, explaining the tour together while competing in Hip Hop contests.
“I sometimes kick myself when I think about what could have been. He was so nice to me, but I really wasn’t feeling him. I guess I couldn’t appreciate a nice guy like Will Smith. He wasn’t thug enough. I was attracted to thugs and hoodlums. Will was too nice to me,” she added.
News of Smith and Denton’s missed connection comes amid the chaos unleashed on the rapper-actor’s marriage after his wife, Pinkett-Smith, made a series of shocking revelations about their relationship to promote her new memoir Worthy — including that they’ve been secretly separated for 7-years.
However, the pair are reportedly working on making their way back to each other.