In a moment that surprised fans and podcast host Shannon Sharpe alike, legendary comedian Damon Wayans Sr. shared a personal—and admittedly awkward—story during a recent appearance on Club Shay Shay. The Poppa’s House star revealed that he once dated a woman who had previously been romantically involved with his nephew.
And it wasn’t just a fling.
“I was in love with her, that’s the thing,” Wayans confessed.
The revelation came roughly two and a half hours into the episode, with Sharpe visibly taken aback by the confession. Wayans, however, handled the topic with his signature humour and candour, even likening the situation to a famous Jackson family love triangle.
“You ain’t never done the Jackson 5?” he joked, referencing the time when Jermaine Jackson married his brother Randy’s ex-girlfriend, Alejandra Oaziaza, in 1995.
Hollywood Dating Pools and Family Boundaries
Wayans, 64, explained that the relationship happened sometime around 2001 or 2002, shortly after his divorce from Lisa Thorner, with whom he shares four children. He admitted to being single for about two years before falling for his nephew’s former flame.
“Do you know how small the dating pool is out here in Cali?” he asked, half-laughing. “This was 2001—things were different!”
Still, despite the unconventional connection, Wayans made sure to approach the situation with respect. Before pursuing anything romantic, he checked in with his nephew to see if the relationship would cross any family lines.
“I’m like, you know, ‘What’s up?’ and he’s like, ‘That’s you,’” Wayans recalled. “And I’m like, ‘Okay, pass the Courvoisier, let’s go!’”
The relationship blossomed, and although it didn’t become a long-term partnership, Wayans admitted he genuinely fell in love. Yet, unsurprisingly, the family dynamics were never quite the same.
“Family gatherings [are] awkward,” he admitted.
A Family Affair — On and Off Screen
Damon Wayans Sr. isn’t just known for his stand-up and classic sketch comedy; his latest project, Poppa’s House, continues to keep it all in the family. The CBS sitcom, which has wrapped up its first season, stars Wayans alongside his real-life son, Damon Wayans Jr.
The show has been well-received by fans, who appreciate the real-life father-son chemistry. As season one comes to a close this month, viewers are already eager to see if the sitcom gets picked up for a second season.
While Wayans’s dating life may have caused a few raised eyebrows at family functions, there’s no denying the bond the Wayans clan shares—on screen and off. If anything, the candid confession only reinforces why audiences love Damon: he’s honest, funny, and refreshingly human.
Why This Story Matters
In an industry where personal stories are often polished for public image, Damon Wayans Sr.’s openness reminds us that even celebrities navigate the complicated waters of love, family, and second chances. His honesty, mixed with humour and a dose of humility, makes the tale not just headline-worthy but also relatable to anyone who’s ever faced an awkward family moment.
While dating a nephew’s ex isn’t exactly a move from the “How-To” relationship handbook, Wayans’s experience also highlights the importance of communication and mutual respect—even in unconventional situations.
