The Men in Black actor opened up on his brief fling

Will Smith is no ordinary man to date as one of Hollywood’s most recognizable figures. Back when he was an aspiring actor and rapper, though, there would come a time where he felt ‘terrified’ when he went out on a date with a woman arguably more famous than him.

Long before he met his wife Jada Pinkett-Smith and had his three children, Fresh Prince of Bel-Air star once took Sandra Denton out on a date in the late 1980s.

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Denton is better known as ‘Pepa’ in the female rap duo Salt-N-Pepa, who are famous for their hit singles ‘Push It!’ and ‘Whatta Man’.

Will Smith and Sandra Denton

When Smith finally got his chance to ask her out on a date, he didn’t hesitate for a second – having eyeballed the singer for a date a long time before when she was spoken for.

The Bad Boys actor was also not shy in admitting he had a crush on Denton when she made an appearance on his Class of ’88 podcast earlier this year. “Now, she was single,” he said. “We was both going to be in LA at the same time, so I’mma shoot my shot.

“This girl was special and I wanted to impress her, so I rented a white Mercedes convertible just because I needed to floss a little bit. My plan was then to take her around Hollywood Hills, drive up Mulholland and all that, watch the sunset.”

Now 55, the Oscar winner admitted that unlike his suave character in the Fresh Prince, he felt “terrified” and used confidence as a mask for his true feelings.

“I always faked like I had game. I didn’t really have game,” he added. “I was always in this full-on, trying to give the wildest flavor of having game. But that might have been the most terrified I had ever been trying to shoot my shot with Pepa. And I didn’t believe I had a real shot.”

In one encounter on their date, Denton recalled how Smith handed a homeless man a $100 bill, a gesture she described as “so nice”. Smith, however, then said: “My concern was that I was going to get killed. That was my concern when I was trying to spit my game, but I ain’t really have nothing.”

Of course, he lived to tell the tale and after a brief time together, their romance fizzled out.

Smith went on to marry his wife Jada in 1997 and while they are still together, the couple have had to battle against rumors of infidelity. Meanwhile, Denton divorced rapper Treach in 2001 after two years of marriage.