Close Menu
The Shade RoomThe Shade Room
  • SHOWS
  • CELEBS
  • NEWS
  • BEAUTY & STYLE
  • TSR TEENS
  • TSR SHOP
  • ROOMIE DIARIES
  • NEWSLETTER
  • CAREERS
  • ADVERTISE WITH US
  • GET FEATURED
Facebook X (Twitter) Instagram YouTube TikTok Snapchat
Trending
  • Mini RiRi? Fans Go Off After NEW Flicks Show Baby Rocki Out With A$AP Rocky (PHOTOS)
  • Whoa! World Health Organization Declares International Emergency Amid Rare Ebola Outbreak (VIDEO)
  • Still THAT Girl! Kandi Burruss Turns 50 With Steamy New Post & Fans Are Saying She’s The Birthday (PHOTO)
  • Awww! Stefon Diggs Celebrates His Daughter Peyton’s First Birthday With Epic Circus-Themed Bash (VIDEOS)
  • IKTR! Yung Miami Turns Up With Her Dad In Viral Clip & Fans Can’t Get Enough Of Their Energy (VIDEO)
  • Prayers Up! Suspected Drunk Driver Reportedly Faces Charges After Fatal Sidewalk Crash Kills Two Men (VIDEO)
  • You Go, Girl! Social Media Celebrates As Flau’jae Johnson Graduates From Louisiana State University (VIDEO)
  • Wildin’ Or Nah? Young Thug & Plies Speak Out Amid Chaos Over Audemars Piguet x Swatch Collaboration (PHOTOS + VIDEOS)
  • Family Of Caleb Wilson Walks Across Southern University Stage In Emotional Graduation Tribute After Hazing Death (VIDEO)
  • Main Character! Taina Williams’ Daughter Emmy Hilariously Stunts On Her After G Herbo’s Gift & The Internet Is Cracking Up (VIDEO)
The Shade RoomThe Shade Room
The Shade Room Text Logo
Facebook X (Twitter) Instagram YouTube TikTok Snapchat
  • SHOWS
  • CELEBS
  • NEWS
  • BEAUTY & STYLE
  • TSR TEENS
  • TSR SHOP
  • ROOMIE DIARIES
  • ADVERTISE WITH US
The Shade RoomThe Shade Room
Home » Latest Tea » Will Smith and Pepa Of Salt-N-Pepa Stir ‘What If’ Convos After Revealing Their One Date
Celebs

Will Smith and Pepa Of Salt-N-Pepa Stir ‘What If’ Convos After Revealing Their One Date

Cassandra SantiagoBy Cassandra Santiago2023/10/30
Facebook Twitter Pinterest LinkedIn Tumblr Email
Will Smith & Pepa Spark "What If" Talks After Revealing Past Date
(L) LOS ANGELES, CA - FEBRUARY 06: Musical artists Cheryl "Salt" James (R) and Sandra "Pepa" Denton attend the Los Angeles Premiere of United Skates from HBO on February 6, 2019 in Los Angeles, California. (Photo by Jeff Kravitz/FilmMagic for HBO) (R) LONDON, ENGLAND - MAY 09: Will Smith attends the "Aladdin" European Gala at Odeon Luxe Leicester Square on May 09, 2019 in London, England. (Photo by Karwai Tang/WireImage)
Share
Facebook Twitter LinkedIn Pinterest Email

Will Smith and Pepa have fans’ imaginations running wild all over social media! The Hollywood friends sparked “what if” dating conversations after revealing they went on one date back in the day.

Their talk happened on Will’s new hip hop history podcast, “Class of ’88.’ The actor sat down with the members of the iconic Salt-N-Pepa group in a recent episode. During their conversation, Will asked Pepa if she remembered the time he took her on a date.

She said yes, and they exchanged looks until Will reassured her they were “allowed”  to talk about it now. He added, “We’ve matured, we ain’t do nothing.” 

RELATED: Jada Pinkett Smith And Will Smith Separated In 2016, But Kept It Private

Will Smith Reveals What Shook Him On Date With Pepa

Pepa started by saying Will was “very nice” and proved it further when he stopped and gave an unhoused man $100 during their date. Will clarified that they drove around Los Angeles and visited the Hollywood sign.

Despite wanting to “spit game,” Will Smith said he was worried about Pepa’s ex-boyfriend. At the time, it hadn’t been that long since Pepa and Treach of Naughty by Nature had broken up. So, Will said he was distracted by how the rapper would take their date.

“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 jumped into the conversation, adding that death “was a legit concern.” Her response had her, Will, and Pepa laughing.

See the clip below.

Social Media Reacts To Will & Pepa’s Date

After the clip of Will and Pepa discussing their date went viral, fans commented on Will having a Jada-less life.

https://twitter.com/msdominiiqueeee/status/1718692075389206927?s=20https://twitter.com/BACStratus_/status/1718442227469635950?s=20

Pepa loved Treach down. Who y'all think her part in Whatta Man is about? Every time she would sing that song, y'all would've said she is disrespecting Will. So miss me with the we could've had it all.

— Meka (@mylife82_) October 28, 2023

Pepa tryna see if Will want that old thang back she ain’t low😂 https://t.co/vBENWKjqLQ

— The Dark Vagician (@_tuckerfooley) October 28, 2023

This isn’t the first time Pepa’s reportedly commented on Will Smith. Like the fans, she previously praised his generosity and spoke on what life could’ve been with him versus 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 told Global Grind. “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.”

Jada Pinkett Smith’s memoir rollout brought some of their marriage secrets to light and caused a ripple of mixed reactions. The most shocking news happened to be Will and Jada’s seven-year separation leading up to the Chris Rock Oscars slap.

Amid the media storm, Smith stepped with Jada to a book reading in Baltimore. There, he told the audience that he would always support his “best friend.” Adding that he’s accomplished so many of his dreams “on the foundation of Jada’s sacrifices.” 

RELATED: Will Smith Professes Everlasting Support For Jada Pinkett Smith
What Do You Think Roomies?
+1
0
+1
0
+1
0
+1
0
+1
0
+1
0
+1
0
Share. Facebook Twitter Pinterest LinkedIn Tumblr Email

Related Posts

Mini RiRi? Fans Go Off After NEW Flicks Show Baby Rocki Out With A$AP Rocky (PHOTOS)

2026/05/17

Whoa! World Health Organization Declares International Emergency Amid Rare Ebola Outbreak (VIDEO)

2026/05/17

Still THAT Girl! Kandi Burruss Turns 50 With Steamy New Post & Fans Are Saying She’s The Birthday (PHOTO)

2026/05/17
Latest Posts

Mini RiRi? Fans Go Off After NEW Flicks Show Baby Rocki Out With A$AP Rocky (PHOTOS)

2026/05/17

Whoa! World Health Organization Declares International Emergency Amid Rare Ebola Outbreak (VIDEO)

2026/05/17

Still THAT Girl! Kandi Burruss Turns 50 With Steamy New Post & Fans Are Saying She’s The Birthday (PHOTO)

2026/05/17

Awww! Stefon Diggs Celebrates His Daughter Peyton’s First Birthday With Epic Circus-Themed Bash (VIDEOS)

2026/05/17

#TSRExclusive

Not you missing out on our newsletter, tap in & sign up!

About
About

TSR is the culture's definitive source for trending celeb news, exclusive interviews, videos, and more.

NMSDC CERTIFIED

Facebook X (Twitter) Instagram YouTube TikTok Snapchat
Latest Posts

Mini RiRi? Fans Go Off After NEW Flicks Show Baby Rocki Out With A$AP Rocky (PHOTOS)

Whoa! World Health Organization Declares International Emergency Amid Rare Ebola Outbreak (VIDEO)

Still THAT Girl! Kandi Burruss Turns 50 With Steamy New Post & Fans Are Saying She’s The Birthday (PHOTO)

Featured Posts

Prayers Up! Suspected Drunk Driver Reportedly Faces Charges After Fatal Sidewalk Crash Kills Two Men (VIDEO)

You Go, Girl! Social Media Celebrates As Flau’jae Johnson Graduates From Louisiana State University (VIDEO)

Family Of Caleb Wilson Walks Across Southern University Stage In Emotional Graduation Tribute After Hazing Death (VIDEO)

© 2026 The Shade Room
  • Celebs
  • News & Politics
  • Beauty & Style
  • Shows
  • TSR Teens
  • TSR Shop
  • Privacy Policy
  • Terms & Conditions
  • Advertising Guidelines

Type above and press Enter to search. Press Esc to cancel.