Damon Wayans Sr. stirred up some conversation during his appearance on Shannon Sharpe’s Club Shay Shay podcast, revealing that he once dated his nephew’s former girlfriend. While the revelation left Sharpe visibly shocked, Wayans defended his actions, explaining that he didn’t see anything wrong with it.
Sharpe, clearly taken aback, asked, “Hold on, this can’t be true, that you dated the same woman as your nephew once?” Wayans responded casually, “Yeah, I was in love with her, that’s the thing,” before jokingly referencing the famous Jackson family’s dynamic by asking, “You ain’t never did the Jackson Five?”
Family Dynamics and Sharing Love
Sharpe responded with disbelief, saying, “Hell no! I mean, for a family member, that’s off-limits, Damon.” But Wayans continued, brushing off the perceived taboo of dating a family member’s ex. He explained the context behind his relationship with his nephew’s former girlfriend, noting that at the time, both he and his nephew were not deeply invested in the relationship.
Wayans explained, “No, but it wasn’t like they were in love. Do you know how small the pool is out here in Cali? The dating pool. This was probably 2001-2. … I got divorced, and I was by myself for two years. And then I saw her and I was just like, ‘Oh my God, I’m in love.’” Upon learning that his nephew had previously dated the woman, Wayans casually asked, “What’s up with that?” His nephew’s response, according to Wayans, was simple: “That’s you.” And just like that, Wayans proceeded with the relationship, even humorously adding, “Okay, pass the Courvoisier. Let’s go!”
While the casual approach to the situation might raise some eyebrows, Wayans appeared unfazed, stating, “And I went and I fell in love. And it was okay!”
The Wayans Family and Business Success
Later in the nearly three-hour interview, Sharpe brought up the financial side of the Wayans family’s success, specifically mentioning Damon’s brothers, Shawn and Marlon Wayans, and how they didn’t earn much from The Wayans Brothers show. Damon, however, highlighted his own financial success from My Wife and Kids, a sitcom that ran from 2001 to 2005.
He expressed that while his brothers didn’t make much money from The Wayans Brothers show, he did quite well with My Wife and Kids, even joking about still receiving checks for the show. “It was on a network, right?” Damon said, in reference to The Jamie Foxx Show. “I made a lot of money off of My Wife and Kids. I can’t relate to that.”
Damon added, “With WB, my brothers didn’t really make money off The Wayans Brothers show. Like I said, I made a lot of money from Wife and Kids. I still get checks. Not to rub it in, but I still get checks.”
Conclusion
Damon Wayans Sr.’s candid conversation about his personal life, family dynamics, and financial success provided insight into the unfiltered nature of his personality. Whether it’s his controversial love life or his continued success in Hollywood, Wayans is always ready to speak his mind—no matter the topic.
