Damon Wayans Sr. Reveals That He Once Dated His Nephew’s Ex-Girlfriend

Nationwide — Damon Wayans Sr. recently shared an interesting family story on the Club Shay Shay podcast, revealing that he once dated his nephew’s ex-girlfriend. The comedian, 64, explained that after his divorce in 2001, he fell in love with the woman, only to later discover she had been in a relationship with his nephew.

During the conversation with host Shannon Sharpe, 56, Damon shared that he was immediately drawn to the woman when they first met. Despite learning about her past relationship with his nephew, Damon clarified that his nephew wasn’t deeply involved with her, according to People. To avoid any family tension, Damon checked with his nephew before pursuing the relationship.

“I’m like, you know, ‘What’s up?’ and he’s like, ‘That’s you.’ And I’m like, ‘Okay, pass the Courvoisier, let’s go!’ And I went ahead and I fell in love and it was okay,” he said and added, “Family gatherings is awkward.”

Damon’s family has long been known for their collaborative work, especially in entertainment. His older brother, Keenen Ivory Wayans, is the creator of In Living Color, where Damon and his siblings frequently appeared. Damon’s latest project is Poppa’s House on CBS, where he stars alongside his son Damon Wayans Jr. and his brother Marlon Wayans.

Damon also shared how working with family feels natural for him. He said, “The thing that takes actors years to develop, we have that automatically, which is chemistry and trust.”