What Really Happened When Will Smith, Pepa Went On a Date? – The Root

We’ve been hearing a lot of stories lately about Jada Pinkett Smith’s past romances. However, her life partner Will Smith just dropped an interesting memory that has hip-hop fans playing detective. On his Class of ‘88 podcast, the Fresh Prince and rap legends Salt-N-Pepa discussed the night he and Pep went on an awkward date.

It all started with the Oscar winner reminding Pepa that they once went out on a date. After some questioning looks that definitely said, “Are we about to tell this story?,” Will responded, “We’re allowed to talk about it! We’ve matured! We ain’t do nothin.’”

The “Whatta Man” singer revealed that Will was “very nice” as they “went for a drive” and visited the Hollywood sign, even stopping to give a homeless person $100. Will relayed that even though Pepa and Naughty by Nature’s Treach were broken up at the time, he was still worried about possible retaliation from 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,” he said. Salt jumped in to confirm, “That was a legit concern,” which had all three laughing hysterically.

Turns out, there wasn’t anything juicy or embarrassing about this story. But the way the three of them looked at each other throughout the tale, as well as Will and Pepa’s obvious glossing over the night in question led many on social media to wonder what really happened during that date. On the Instagram video of the conversation, commenters had thoughts on what really went down.

“He said ‘we all grown! we can talk about it!’ Then they all started stuttering lmao,” replied one user.

Not believing this clean version of the story, another person replied, “Lmao a lot more happened on this date for sure with all these stutters and beats.”

Someone else noticed that Pepa’s partner wasn’t completely on board with recalling the date, writing, “Lol [at] Salt looking stressed like sis wait…you about to tell too much.”

One person noted that the “Summertime” rapper may have had more game than we knew, writing, “Will had Treach and PAC girls!!!! I’m just saying! Who’s really winning here!!! Nice guys don’t always finish last we just have more class.”

Will Smith has been a movie star for so long, some fans have forgotten that the man is also a rap legend. It’s always fun to see him jump back into his rap roots, so Class of ‘88 should offer a lot more of these fascinating untold stories of hip-hop history.

All episodes of Class of ‘88 are now available on Audible.