Will Smith & Pepa's Old Date Story Leaves Fans Demanding A Reunion

Fans think Will Smith and Pepa should rekindle their romance.

BYCaroline Fisher
"Aladdin" Premiere In Berlin

On a recent episode of Will Smith's Class of '88 podcast, he and Pepa recalled going on a date together back in the day. Obviously, their relationship didn't pan out. Pepa went on to marry Treach while Smith tied the knot with Jada Pinkett Smith. Now, however, it appears as though both of them are single, leaving fans wondering what would happen if they gave each other another shot.

“Okay, you were very nice," Pepa said of their date. "This was the date you won and beat us out. You was so happy. You was like let’s go celebrate. 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."

Read More: Will Smith Recalls Fear Over Going On Date With Pepa Due To Treach Romance

Will Smith & Pepa Once Went On A Date

“I think you and Treach had been broke up for a minute," Smith added. "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." On top of the sweet story, Pepa previously opened up about her fling with Smith in a 2009 interview with Global Grind, revealing that she had some regrets. She had nothing but flattering things to say about Smith, and expressed curiosity about what her life would have been like had she chosen him over Treach.

“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,” she revealed. “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."

Fans Want Will Smith & Pepa To Rekindle Their Romance

What do you think of the story of Will Smith and Pepa's date? Do you think they should rekindle their romance? Share your thoughts in the comments section, and keep an eye on HNHH for more updates. Check out some social media users' reactions down below.

Read More: Will Smith And Jada Pinkett Smith Roasted On SNL


  • Link Copied to Clipboard!
About The Author
Caroline Fisher is a News Writer at HotNewHipHop from Chicago, Illinois. She started at HNHH this year, and has since spent her time writing about all that is newsworthy in the world of hip-hop. With a drive for hunting down the hottest stories, she enjoys documenting new developments in culture and entertainment. She also has an appreciation for hip-hop and seeks to cover the most important trends and shifts. She has a Bachelor of Arts which she received at the University of Illinois at Chicago. Having graduated in 2022, she majored in English with a concentration in Media, Rhetoric and Cultural Studies. Specializing all things music, pop culture and entertainment, some of her favorite musical artists include Snoop Dogg, OutKast, and Nicki Minaj. When she’s not writing about music she’s also a fan of attending shows, watching the latest movies, staying up-to-date with current events, photography, and poetry.