During a revealing conversation on Shannon Sharpe's 'Club Shay Shay' podcast, Damon Wayans Sr. opened up about a past relationship that blurred family boundaries, leaving Sharpe — and likely many listeners — stunned.

In the second half of the April 2 episode, Wayans recounted how, shortly after his divorce from Lisa Thorner in the early 2000s, he fell for a woman his nephew had once dated. "Yeah, I was in love with her. That's the thing," he told Sharpe when the topic came up.

Wayans likened the situation to the Jackson family's complex romantic history, asking, "Come on, you ain't never did... you never did Jackson 5?" Sharpe quickly dismissed the comparison: "Hell nah, I ain't never did that. I mean, for a family member, that's off limits, Damon." Wayans replied, "No, but... It wasn't like they were in love."

He recalled being alone for a couple of years after the split when he met the woman, later realizing she had dated his nephew. "You know what's up with that?" he said he asked. The response? "Ohh, that's you..." To which Wayans answered, "OK, pass the Courvoisier, let's go."

56th NAACP Image Awards - Arrivals
PASADENA, CALIFORNIA - FEBRUARY 22: (L-R) Amara Wayans and Damon Wayans attend the 56th NAACP Image Awards at Pasadena Civic Auditorium on February 22, 2025 in Pasadena, California. Aaron J. Thornton/Getty Images for BET

Though he didn't name her, sources claim the woman was Charity Duplechan. Wayans praised her, saying, "If you had seen her, you understand... and she cooked? She went to Cordon Bleu." He added she made "desserts" and "was a bona fide chef."


When asked about the family impact, Wayans admitted, "Family gatherings is awkward." Despite this, the Wayans clan continues to thrive, recently honored with the NAACP Hall of Fame Award, and still collaborating on major projects across film and television.

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