Damon Wayans Sr. Reveals Shocking Family Dating Triangle That Left Host Speechless

Damon Wayans Sr. Admits to Dating His Nephew’s Ex in Jaw-Dropping Podcast Confession

In a revelation that left even seasoned interviewer Shannon Sharpe visibly shocked, Damon Wayans Sr. has admitted to dating his nephew’s former girlfriend following his divorce. The 64-year-old comedy legend made the surprising confession during a recent appearance on the popular Club Shay Shay podcast, describing the situation as “love at first sight.”

The “My Wife and Kids” star didn’t hold back as he recounted the unconventional romance that began around 2002, just two years after his marriage to Lisa Thorner ended. What makes this confession particularly eyebrow-raising? Wayans apparently had no idea about the family connection when he first fell for the unnamed woman.

“I Was In Love With Her” – A Defensive Damon Explains

When Sharpe questioned the appropriateness of dating a relative’s former partner, Wayans defended himself with surprising candor. “I was in love with her, that’s the thing,” the comedian explained, before asking his incredulous host, “Come on, you ain’t never did… you never did Jackson 5?”

Sharpe’s response was immediate and unequivocal: “Hell no, I ain’t never did that. I mean, for a family member, that’s off limits, Damon.” The exchange highlights the generational or personal differences in dating boundaries within Hollywood families that continue to fascinate fans.

Wayans attempted to minimize the potential family conflict by clarifying, “It wasn’t like they were in love,” suggesting the previous relationship between his nephew and the woman wasn’t serious enough to prevent his pursuit.

The Timeline: Post-Divorce Romance That Raised Eyebrows

According to Wayans, the unexpected romance blossomed during a vulnerable period in his life. “I got divorced and I was by myself for two years,” he recalled on the podcast. “And then I saw [his nephew’s ex] and I was just like, ‘Oh my God. I’m in love.'” It wasn’t until after this powerful connection that he discovered the awkward family link.

The comedian, who was married to Lisa Thorner from 1984 to 2000 and shares four children with her, described having an honest conversation with his nephew about the situation. The younger Wayans’ reported response? “That’s you” – apparently giving his uncle permission to pursue the relationship.

In typical Wayans fashion, he wrapped this serious moment in humor, adding, “And I’m like, ‘OK, pass the Courvoisier, let’s go!'” The Wayans family dynamics have always been a source of public fascination, with their extensive comedy empire spanning generations of performers.

Family Gatherings Turned “Awkward” After the Romance

While Wayans maintained that the relationship was worth pursuing despite its unusual beginnings, he did acknowledge one predictable downside. “Family gatherings” became “awkward” in the aftermath of his dating decision – something that shouldn’t surprise anyone familiar with complicated family dynamics.

The actor carefully avoided revealing either his nephew’s identity or naming the woman at the center of this love triangle. Given the extensive Wayans family tree in Hollywood, with numerous successful actors, directors, and performers, fans have been left speculating about which family member might have been involved.

A Career Built on Pushing Boundaries

This revelation follows Damon Wayans Sr.’s long-established pattern of pushing boundaries both on and off screen. As one of the creative forces behind groundbreaking comedy series like “In Living Color” and a successful stand-up career, Wayans has rarely shied away from controversial topics or personal revelations.

His candid admission on Sharpe’s podcast demonstrates the same fearlessness that has characterized his comedy for decades. Whether fans find the situation amusing or uncomfortable likely depends on their own family values and boundaries.

While some might question the wisdom of dating within such close family circles, Wayans seems to have no regrets about following his heart, concluding simply: “And I went ahead and I fell in love and it was OK.”

What Do You Think?

Did Damon Wayans Sr. cross an unspoken family boundary, or was this simply a case of two adults making their own choices after getting proper clearance? The debate continues as fans process this unexpected glimpse into the personal life of one of comedy’s most recognizable family dynasties.

One thing’s certain – Shannon Sharpe’s podcast continues to deliver headline-making revelations from its celebrity guests, cementing its place as a must-watch for anyone interested in unfiltered celebrity confessions.