The rapper turned actor said he had been patiently waiting to take out Sandra "Pepa" Denton when he finally got a chance in early 1988.
"I always had a thing for Sandy, but she was always dating somebody else," Smith said during the episode transcribed by People. "Now she was single. We was both going to be in L.A. at the same time, so Imma shoot my shot."
He knew he had to pull out all the stops to impress Denton. Salt-N-Pepa had just released their hit single "Push It" the year prior.
"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," Smith said. "My plan was then to take her around Hollywood Hills."
Denton recalled Smith engaging in a sudden act of kindness.
"We were out and we saw a homeless person and you gave the homeless person $100," she said. "It was so nice."
But Smith was still sweating bullets the entire time and the pair didn't end up going on a second date.
"My concern was that I was going to get killed," he said. "That was my concern when I was trying to spit my game, but I ain’t really have nothing… 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."
Smith had a big year in 1988 with the release of hit singles including "Parents Just Don't Understand" and "A Nightmare on My Street." He was known as the Fresh Prince at the time and performed alongside DJ Jazzy Jeff.
The pair reunited earlier this year for a performance at A Grammy Salute to 50 Years of Hip-Hop.
In 1990, Smith launched his acting career by starring in the NBC program The Fresh Prince of Bel Air. The last new episodes were recorded in 1996, but reruns of the show are still common to this day.
To promote the podcast episode, Smith also filmed a short video with Salt-N-Pepa that was posted to his Instagram account. In the clip, he and the duo recreate a vintage picture while Simple Plan's track "I'm Just a Kid" plays in the background.
Smith apparently has a thing for other musicians. He ended up marrying Jada Pinkett Smith, who was once the lead singer of the nu metal band Wicked Wisdom. The pair's daughter Willow Smith is now a musician, as well. She's written hits including "Whip My Hair" and "Meet Me at Our Spot."
Smith made global headlines in 2022 when he slapped Chris Rock during the Academy Awards ceremony. This came after the comedian made a joke about Pinkett's struggle with alopecia. Smith was there to accept an award for his performance in King Richard, a biopic about the father of tennis stars Serena and Venus Williams.