On his podcast Class of 88 Will Smith and his guest Pepa revealed they went on the date, and now everyone wants to know what happened.
According to REVOLT 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.”
Will Smith & Pepa of Salt-N-Pepa talk about their first date.
— Episodes (@episodesent) October 28, 2023
and
Salt-N-Pepa connect with Will Smith for the incredible ‘Class of 88’ podcast which I’m a writer on dropping this Thursday on @amazonmusic pic.twitter.com/GRulSMRnn1
— brokencool (@brokencool) October 25, 2023
Twitter reaction:
If I’m Will Smith, I’m asking Pepa if she tryna go to Cheesecake Factory.
“I heard you got regrets, I got regrets too.. what it do?” https://t.co/SqPiEmRBqV pic.twitter.com/FOuyLANyaZ
— B. Chordial (@BChordial) October 27, 2023
and
Will "Fresh Prince" Smith & Salt n Pepa pic.twitter.com/Gg87tAnWEk
— Lonnie Norman (@Aquariuslonn) October 27, 2023
and
Will "Fresh Prince" Smith & Salt n Pepa pic.twitter.com/Gg87tAnWEk
— Lonnie Norman (@Aquariuslonn) October 27, 2023
and
All ima say is, I remember years ago Pepa confessed how Will Smith had a crush on her and she thought he was corny. When she got older she said she regretted not taking him seriously because her life could’ve been so different.? https://t.co/6IIGo9dOjh
— THE ONE. (@50ShadesOfShay) October 27, 2023
and
Will Smith and Pepa could’ve been ????
— Ms. Dominique (@msdominiiqueeee) October 29, 2023
and
Will Smith: We- We- We… ain't do… nothing. We… We just… We just… We-
Pepa: Okay, you were… very… nice.
Will: And it was LA… right?
?? LIKE WHAT!?
— Chile, I guess… (@Breyionna) October 28, 2023
