Will Smith fans are trying to fill in the gaps of a hilarious first date story he shared on his new podcast celebrating hip hop, “Class of ’88.” Back in the day, Smith had the biggest crush on Pepa of the trailblazing group Salt-N-Pepa. In his sit-down with the ladies, he made sure that listeners were entertained by his and the female lyricist’s recollection of the night’s events.
“We went on a date one time. Remember that?” the Hollywood juggernaut first asked. “Yes, I do… I know exactly what happened,” said Pepa before taking a few seconds to contemplate if it was a story she should share. Smith excitedly reassured her, saying, “We’re allowed to talk about it! We’ve matured! We ain’t do nothin’.”
After exchanging a few looks with Salt, Pepa began, “Okay, you were very nice,” but Smith interjected, adding that they were in Los Angeles and “went for a drive.” She would go on to say that their date took place in 1989 after Smith and DJ Jazzy Jeff won their first Grammy for Best Rap Performance. Despite their victory, their win was not televised and sparked a boycott of the awards ceremony, including other hip hop figures like Russell Simmons, LL Cool J, and Salt-N-Pepa.
The New York artist continued, “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.” At the time, Smith said Pepa and Treach of Naughty by Nature had been broken up for a minute, though he still had concerns about a possible run-in with the New Jersey 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,” he said. When Salt suggested, “That was a legit concern,” the trio broke out into laughter.
Fans weighing in found the story comical and full of major plot points. “Lmao a lot more happened on this date for sure with all these stutters and beats,” read a comment on Instagram. On TikTok, where Smith also shared a clip, someone else wrote, “They literally ain’t say nothing about the d**n date. [Something] happened.”