Damon Wayans Sr. isn’t one to hold back when it comes to telling it like it is. During a recent sit-down on the Club Shay Shay podcast with Shannon Sharpe, the comedy legend shared a surprising personal story about dating someone from his family’s past — specifically, his nephew’s ex-girlfriend.
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The 64-year-old actor revealed the relationship happened in the early 2000s, shortly after his divorce from Lisa Thorner. “I was by myself for two years,” he recalled. “And then I saw her and I was like, ‘Oh my God. I’m in love.’”
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Things got a little complicated when he learned his nephew had previously dated the same woman. Before moving forward, Wayans decided to have a conversation with his nephew to make sure there were no issues. “I asked him, ‘What’s up?’ and he said, ‘That’s you,’” Wayans explained. “So I said, ‘Okay, pass the Courvoisier,’ and I went ahead and fell in love.”
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He admitted the situation made family get-togethers a little uncomfortable but insisted everything was above board. When Sharpe questioned the dynamic, Wayans downplayed the drama and cracked a joke, asking if he’d ever “done the Jackson 5,” a playful reference to Jermaine Jackson marrying his brother Randy’s former girlfriend.
Wayans emphasized that his nephew and the woman were not in love, which made it easier for him to pursue the relationship. While he didn’t name the woman, he made it clear the connection was genuine and that he approached it with honesty and respect.
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The Wayans family is known for keeping things close, especially in the entertainment world. Damon rose to fame with his siblings on the iconic sketch comedy show In Living Color, and continues to collaborate with them today. He currently stars in the CBS comedy Poppa’s House alongside his son, Damon Wayans Jr. His brother Marlon has also appeared on the show, and their sister Kim directed an episode.
Even with the occasional family awkwardness, Damon Wayans Sr. remains true to himself — and his love life is no exception.
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