(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)
<p><strong>Will Smith</strong> and <strong>Pepa</strong> have fans&#8217; imaginations running wild all over social media! The Hollywood friends sparked &#8220;what if&#8221; <a href="https://dev.theshaderoom.com/kayla-nicole-therapy-reaction-travis-kelce-taylor-swift-dating/" target="_blank" rel="noopener">dating conversations</a> after revealing they went on one date back in the day.</p>
<p>Their talk happened on Will&#8217;s new <a href="https://open.spotify.com/show/6N2JiKvHDSMjzAnzr42PU4" target="_blank" rel="noopener">hip hop history podcast</a>, &#8220;Class of &#8217;88.&#8217; The actor sat down with the members of the iconic <a href="https://dev.theshaderoom.com/selena-quintanilla-salt-n-pepa-and-more-awarded-with-the-lifetime-achievement-award-at-the-grammys/" target="_blank" rel="noopener">Salt-N-Pepa</a> group in a recent episode. During their conversation, Will asked Pepa if she remembered the time he took her on a date.</p>
<p>She said yes, and they exchanged looks until Will reassured her they were &#8220;allowed&#8221; to talk about it now. He added, <em>&#8220;We&#8217;ve matured, we ain&#8217;t do nothing.&#8221; </em></p>
<h5 style="text-align: center;">RELATED: <a href="https://dev.theshaderoom.com/jada-pinkett-smith-reveals-will-smith-separated-video/" target="_blank" rel="noopener">Jada Pinkett Smith And Will Smith Separated In 2016, But Kept It Private</a></h5>
<h3 style="text-align: center;">Will Smith Reveals What Shook Him On Date With Pepa</h3>
<p>Pepa started by saying Will was &#8220;very nice&#8221; 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.</p>
<p>Despite wanting to &#8220;spit game,&#8221; Will Smith said he was worried about Pepa&#8217;s ex-boyfriend. At the time, it hadn&#8217;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.</p>
<blockquote><p>&#8220;So in my mind, when I was like, I was trying to spit my game, but I ain&#8217;t really had nothin&#8217; cause my concern was that I was gon&#8217; get killed, &#8221; Smith said.</p></blockquote>
<p>Salt jumped into the conversation, adding that death &#8220;was a legit concern.&#8221; Her response had her, Will, and Pepa laughing.</p>
<p>See the clip below.</p>
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<h3 style="text-align: center;">Social Media Reacts To Will &; Pepa&#8217;s Date</h3>
<p>After the clip of Will and Pepa discussing their date went viral, fans commented on Will having a Jada-less life.</p>
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<p>This isn&#8217;t the first time Pepa&#8217;s reportedly commented on Will Smith. Like the fans, she previously praised his generosity and spoke on what life could&#8217;ve been with him versus Treach.</p>
<blockquote><p>&#8220;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,&#8221; she told Global Grind. &#8220;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.&#8221;</p></blockquote>
<p>Jada Pinkett Smith&#8217;s memoir rollout brought some of their marriage secrets to light and caused a ripple of <a href="https://dev.theshaderoom.com/jada-pinkett-smith-chris-rock-once-asked-her-out-rumors-will-smith-divorcing/" target="_blank" rel="noopener">mixed reactions</a>. The most shocking news happened to be Will and Jada&#8217;s seven-year separation leading up to the Chris Rock <a href="https://dev.theshaderoom.com/will-smith-banned-from-the-oscars-for-10-years-after-chris-rock-slap/" target="_blank" rel="noopener">Oscars slap</a>.</p>
<p>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 &#8220;best friend.&#8221; Adding that he&#8217;s accomplished so many of his dreams<em> &#8220;on the foundation of Jada&#8217;s sacrifices.&#8221; </em></p>
<h5 style="text-align: center;">RELATED: <a href="https://dev.theshaderoom.com/will-smith-professes-support-jada-pinkett-smith-best-friend-hes-ever-had-video/" target="_blank" rel="noopener">Will Smith Professes Everlasting Support For Jada Pinkett Smith</a></h5>
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