Damon Wayans Sr.’s decades-long career has yielded many interesting stories, with a majority of them having to do with members of his large family. The veteran actor recently spoke about a questionable chapter in his dating history that consisted of some overlap within his line of descent.
In the latest episode of Club Shay Shay, the two men discussed everything from career highlights to regrets. Host Shannon Sharpe hit him with a straightforward question that people wanted to know more details about: “Did you date the same woman as your nephew once?”
“Yeah,” Damon said with no hesitation, doubling down on the choice he made. “I was in love with her, that’s the thing. C’mon, you ain’t ever did the Jackson 5?” he continued as Sharpe interjected, “Hell nah!”
After the Hall of Famer said family members should be “off limits,” the My Wife And Kids star defended himself by replying, “It wasn’t like they were in love.”
He continued, “Do you know how small the pool is our here in Cali? The dating pool. And this was probably, what, 2001-2… I got divorced and I was by myself for two years. And then I saw her and I was just like, I’m in love. And I found out my nephew had dated her. I’m like, ‘What’s up with that?’ He goes, ‘That’s you.’ I go, ‘Okay. Pass the Courvoisier.’ And I went ahead and I fell in love.”
In terms of the consequences of his actions, he added with a laugh, “Family gatherings is awkward.” Watch the clip above and the full interview below.
Matching the energy of the conversation, the commenters had jokes of their own. “He the uncle you can’t let hug your girlfriend,” one person wrote on TikTok as another one added, “He sound like he ain’t over her.” Another user said, “The pool ain’t that small Damon. Now come on.” One person echoed what many people are thinking, writing, “Investigators do y’all job,” as the men never clarified who the woman was and which one of the Wayans nephews she dated.
Elsewhere in the entertaining interview, Damon told the story about getting punished by his dad for stealing 15 cents, the time Mike Tyson bit his neck, getting fired by Saturday Night Live for saying it’s “too white,” and why he regrets breaking up his marriage.
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