Damon Wayans Sr. is owning up to a family story he knows sounds wild: he says he once dated and “fell in love” with a woman who had previously dated his nephew, a decision he now jokes has made family events “awkward.” Wayans shared the story while talking with Shannon Sharpe on the Club Shay Shay podcast, where Sharpe reacted in disbelief and Wayans leaned into the uncomfortable humor of it all.
Wayans placed the relationship in the early 2000s, after his divorce from Lisa Thorner. He said he didn’t just jump into it without thinking about the family implications: he claimed he spoke to his nephew first and got a green light because, in his words, the nephew and the woman “weren’t in love.” Still, Wayans admitted the dynamic didn’t exactly make for smooth holidays afterward, summing it up with the blunt punchline that gatherings became awkward.
He also tried to contextualize it as a “small dating pool” problem, the kind of rationalization that doesn’t fully erase the weirdness, but does explain how it happened in his mind. In the same conversation, Wayans compared his situation (jokingly) to famous messy family dating history in pop culture, using it as a way to keep the tone comedic even while acknowledging why people would side-eye it.
The confession quickly bounced around online because it hits that rare intersection of celebrity candor and “wait, you did what?” shock value. But the key detail Wayans keeps emphasizing is consent and context: he says he checked with his nephew before getting involved and insists it wasn’t a case of stealing a serious relationship — even if it’s still the kind of thing most families would rather not have in their lore.
