BY: Walker
Published 3 weeks ago
Damon Wayans Sr. found a way to make family gatherings an “awkward” affair.
While appearing on the April 2 episode of the Club Shay Shay podcast hosted by former NFL star Shannon Sharpe, the comedian revealed that he once dated his nephew’s ex-girlfriend.
“I was in love with her, that’s the thing,” Damon, 64, recalled, before jokingly asking Sharpe, “You ain’t never done the Jackson 5?” — a reference to the fact that Jermaine Jackson married brother Randy Jackson’s ex-girlfriend, Alejandra Oaziaza.
Damon Wayans on dating and falling in love with the same woman that his nephew dated. pic.twitter.com/DYAZbEB9LH
— The Art Of Dialogue (@ArtOfDialogue_) April 3, 2025
When Sharpe, 56, questioned the decision, Damon went on to clarify that his nephew and the woman had not been “in love.” He also explained that the relationship began around 2001 after he had split from his then-wife Lisa Thorner.
“I got divorced and I was by myself for two years,” he said. “And then I saw her [his nephew’s ex] and I was just like, ‘Oh my God. I’m in love.’ And then I found out my nephew had dated [her].”
The Major Payne star went on to explain that he then checked in with his nephew to make sure it would be okay to pursue a relationship with the woman.
“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 before joking, “Family gatherings is awkward.”
Damon’s tight-knit family is known for their creative collaborations, both in front of the camera and behind it. His older brother, Keenen Ivory Wayans, 66, wrote and created the iconic sketch comedy show In Living Color, in which Damon and several of his siblings regularly appeared.
Most recently, Damon is starring in the CBS show Poppa’s House alongside his son Damon Wayans Jr., 42. His brother, Marlon Wayans, 52, has also appeared in the series, and their sister, Kim Wayans, 63, has directed an episode.
During a recent interview with PEOPLE, Damon opened up about why working with family feels so right. He said: “The thing that takes actors years to develop, we have that automatically, which is chemistry and trust.”
via: People
