Comedian Damon Wayans Sr. revealed a surprising romantic connection that blurred family lines during his recent appearance on Shannon Sharpe’s “Club Shay Shay” podcast. In part two of the April 2 episode, the comedy legend confessed to dating the same woman his nephew dated following his di vorce in the early 2000s after 16 years of marriage. Damon Wayans makes shocking confession about dating his nephew’s ex-girlfriend. (Photo by Alberto E. Rodriguez/Getty Images) The revelation came during a wide-ranging conversation where Wayans discussed everything from Kanye West’s need for guidance to recognizing Katt Williams’ star potential early in his career. But it was Damon’s candid admission about his romantic life that left Sharpe visibly shocked. “Yeah, I was in love with her. That’s the thing,” Wayans admitted when asked if he had dated the same woman as his nephew, whose name he did not mention. He compared the situation to the infamous Jackson family dynamics, asking Sharpe, “Come on, you ain’t never did… you never did Jackson 5?” Sharpe quickly shot back, “Hell nah, I ain’t never did that. I mean, for a family member, that’s off limits, Damon.” The “Major Payne” actor said, “No, but… It wasn’t like they were in love.” Wayans, now 63, explained that he had been divorced from his ex-wife, Lisa Thorner, and was alone for two years before meeting the woman around 2001 or 2002. When he discovered his nephew had previously dated her, he simply asked about the situation and then proceeded with the relationship. “You know what’s up with that?” he recalled asking his nephew, who replied, “Ohh, that’s you…” Wayans’ response was simple: “OK, pass the Courvoisier, let’s go.” 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 Fans had mixed reactions to his revelation when clips from the interview appeared on The Jasmine Brand’s Instagram. “Men do not care. I’m sure his nephew gave him his blessings,” commented one follower. While another said, “Because men fall in love with their eyes! Before y’all start, a MAN even told me this.” Others were more critical, with one observer bluntly stating, “That’s disgusting and disrespectful” while another added, “LA life is different smh.” Some viewers focused on what might have motivated such a decision. “Nah Damon who was she?! What woman made you say eff you nephew?,” one said, while another asked, “So are they still together?” While the “My Wife and Kids” star never explicitly named the woman during the interview, sources indicate he was referring to Charity Duplechan, author of “Unbelievably Vegan” and current host of her own cooking show on Max streaming. The pair reportedly began dating around 2003, with Duplechan’s culinary skills apparently playing a significant role in Wayans’ affection. View this post on Instagram A post shared by Max (@streamonmax) “If you had seen her, you understand… and she cooked? She went to Cordon Bleu,” Wayans told Sharpe, who seemed increasingly intrigued as the conversation progressed to her culinary abilities. When Sharpe asked if she could cook soul food classics like oxtail and collard greens, Wayans enthusiastically said she could, adding that she was “a bona fide chef” and made “desserts” too. Duplechan has built an impressive career since her days with Wayans. Tennis icon Venus Williams wrote the foreword for her cookbook, praising Duplechan’s approach to plant-based cooking. Currently living in Tennessee, she launched her streaming show “Unbelievably Vegan With Chef Charity” in 2024 and has been photographed socializing with celebrities like Kim Kardashian and Sandra “Pepa” Denton over the years. The unusual romantic overlap isn’t unheard of in entertainment’s royal families. As he mentioned in the interview, the Jackson clan experienced a more complicated version of this phenomenon when Jermaine Jackson married his brother Randy’s ex-girlfriend Alejandra Oaziaza in 1995. View this post on Instagram A post shared by Nostalgiaculture – (@nostalgiaamoments) Alejandra had already had two children with Randy before having two more with Jermaine, creating a situation where the children were both half-siblings and cousins. Relating to their unusual family situation, Wayans admitted, “Family gatherings is awkward,” referring to the Wayans Dynasty. The brothers — Keenen Ivory, Damon, Shawn, and Marlon — were recently honored with the NAACP’s Hall of Fame Award in February 2025. They remain committed to expanding their entertainment empire. The family continues working together professionally, with Marlon recently appearing on Damon’s CBS show “Poppa’s House” in an episode directed by their sister Kim Wayans. As the Wayans brothers collaborate on new projects, including Marlon and Shawn’s commitment to another “Scary Movie” installment, they prove that family ties, however complicated by past romantic entanglements, remain the foundation of their enduring success in Hollywood. ‘It Wasn’t Like They Were In Love’: Damon Wayans Says Family Gatherings Got ‘Awkward’ After He Fell ‘In Love’ with His Nephew’s Ex ...read more read less