During the sit-down chat, the actor got candid about a tumultuous time in their marriage of more than 20 years and he didn't hold back.
In a clip for the episode, the A-list actor recalled a moment Jada cried for "45 days straight" as they were hitting some roadblocks in their marriage.
"There was a period where mommy woke up and cried 45 days straight — I started keeping a diary," he told Willow before Pinkett-Smith jokingly interjected that he "missed some days."
"It was every morning," he continued. "I think that's the worst I've ever felt in our marriage. I was failing miserably."
Watch them share a bit about the elusive moment in the teaser, below:
Red Table Talk has proven to be quite the hit since its premiere, earlier this year. It has since earned a 2018 People's Choice Award nomination for daytime talk show and saw Pinkett-Smith dish on a slew of topics her fans would never have learned her views on from her 17-year-long feud with Gabrielle Union to her dating Smith before he was divorced from his first wife.
Red Table Talk returns to Facebook Watch on October 22 with all new episodes.