Will Smith and Salt-N-Pepa’s Sandra “Pepa” Denton revisited their one date on Smith’s Class of ’88 podcast. Denton remembered Smith giving a homeless person $100 and the pair going to the Hollywood sign; Smith recalled feeling nervous because of her past relationship with Treach. Published accounts disagree on whether the date happened in 1988 or 1989.
What Smith and Denton remembered
Smith prompted the recollection by asking, “We went on a date one time. Remember that?” Denton replied, “I know exactly what happened,” according to Black Enterprise’s account of the podcast conversation.
Denton described Smith as “very nice.” She recalled that during their outing he noticed a homeless person and gave them $100, then the two went to the Hollywood sign. Her account makes the small act of kindness the detail she most clearly emphasized.
Why Smith said he was nervous
Smith remembered worrying that he might be killed because Denton had previously dated Treach, the rapper from Naughty by Nature. “My concern was that I was gon’ get killed,” he said, as quoted by Black Enterprise. The account also says Salt considered Smith’s concern legitimate. This was Smith describing his own nerves; it does not establish that anyone threatened him.
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Why reports give two different years
The date’s year is unsettled in the published coverage. Revolt’s October 2023 report places it in 1989, after Smith and DJ Jazzy Jeff won a Grammy. By contrast, an IOL report carrying Bang Showbiz coverage quotes Smith recalling “sometime in early ’88.” Neither version resolves the discrepancy, so the year should be treated as uncertain rather than choosing one account as fact.
Additional details in Smith’s recollection
The IOL/Bang Showbiz report says Smith recalled renting a white Mercedes convertible and planning to drive through the Hollywood Hills. It also quotes him saying, “This girl was special and I wanted to impress her.” These are details carried in syndicated coverage of his podcast recollection, not independently verified logistics.
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