Will Smith Went On One Date With Pepa But Feared He ‘Was Gonna Get Killed’ By Treach

Will Smith went on one date with Pepa from Salt-N-Pepa, but Treach from Naughty By Nature halted any hopes the Fresh Prince had of taking the relationship further.

Smith dipped back into his Fresh Prince bag for his Class of ’88’ podcast that celebrates a pivotal year in hip-hop history. With the art form celebrating its 50th anniversary, Smith is doing his part in honoring the music genre that helped launch his successful Hollywood career by sitting down with fellow rap pioneers and reliving memories from those early days of hip-hop.

In a recently released excerpt from the new show, Smith sat down with Salt-N-Pepa where he and Sandra Denton, or “Pepa,” recall the one date night they enjoyed back in their youth. Denton said the Philadelphia native was “too nice” for her liking.

“We went on a date one time. Remember that?” Smith asked.

“Yes, I do… I know exactly what happened,” Pepa said before taking time to think about what she could share.

“We’re allowed to talk about it! We’ve matured! We ain’t do nothin’,” Smith joked.

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Salt-N-Pepa were touring with Fresh Prince and Jazzy Jeff at the time. The Philly duo had beat out the rap femcees along with LL Cool J for Best Rap Performance at the 1989 Grammy Awards.

“OK, you were very nice,” Pepa said of the date that Smith noted was just a drive through Los Angeles. “This was the date you won and beat us out. You was so happy. You was like, ‘Let’s go celebrate.’ We were out, and then you saw a homeless person, and you gave the homeless person $100, and it was so nice. And then we went to the Hollywood sign,” Pepa recalled.

Smith noted that Pepa and Treach had been broken up for some time at the time of the date. But the “Parents Just Don’t Understand” rapper was still worried he might ignite a feud with the “Hip Hop Hooray” rapper.

“So in my mind, when I was like, I was trying to spit my game, but I ain’t really had nothin’… ’cause my concern was that I was gon’ get killed,” Smith said.

Salt added that it “was a legit concern,” which prompted a laugh from the trio. Fans who watched the teaser felt like there was more to the date than just a drive through LA considering all the “stutters,” as one viewer pointed out.

“A lot more happened on this date for sure with all these stutters and beats,” they wrote.

“Oh Lawd! They think we can’t read between the lines,” added someone else.

Will’s Class of ’88 podcast can be heard HERE.