"Family gatherings is awkward" — Damon Wayans on dating the same woman that his nephew dated

On April 2, 2025, comedian and actor Damon Wayans shared his dating experience while speaking to Shannon Sharpe on the Club Shay Shay podcast. At one point during the conversation, Sharpe said:

“Hold on, this can't be true. That you dated the same woman as your nephew once.”

Wayans admitted it happened and said he had strong feelings for her. Sharpe said he wouldn’t cross that line, but Wayans explained that his nephew and the woman weren’t seriously involved. He added that dating options in California were limited, and this happened back in the early 2000s.

When asked if either of them knew about the overlap at first, Wayans explained he had just gotten divorced and, after reconnecting with her, realized his nephew had dated her. However, the nephew gave him the green light.

Damon Wayans said:

“And I went ahead and and I fell in love. Fell in love and it was okay.”

He went on:

“Family gatherings is awkward.”

Shannon Sharpe weighed in, saying he would have just walked away from the situation, but Wayans explained that it wasn’t easy for him. He said the woman was beautiful and also an incredible cook who had trained at Le Cordon Bleu.

Damon Wayans was married to Lisa Thorner until they split in 2000. According to Complex, around that time, he was also working on his sitcom My Wife and Kids, which he said became a comforting space during the difficult period. When asked if filming the show in between a divorce was tough, he explained that comedians often use personal struggles as creative fuel.

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Damon Wayans talks about managing diabetes

Shannon Sharpe asked Damon Wayans about managing his type 2 diabetes. Wayans compared it to dealing with a club foot. He said he was diagnosed in 2017 and explained that diabetes was a genetic condition in his family. However, using a glucose monitor was helpful as it lets him track his blood sugar levels.

Before using it, he didn’t realize how certain foods affected his body. He shared that he once went to the hospital feeling disoriented, only to find that his blood sugar was high, around 535, when a normal range is between 80 and 120. Then, Damon Wayans said:

“So, I tell Keenan and Kennan's like, ‘Okay you got to change your diet.’ I go, ‘What do you mean?’ He goes, ‘Well, if you don't eat sugar, you won't have a sugar problem.’”

Damon Wayans shared that Keenan Wayans went through his kitchen and pointed out how many everyday foods, like ketchup, were loaded with sugar. That made him realize just how much sugar was in the things he liked.

At the time, he relied on insulin with every meal, which he didn’t enjoy, especially the constant finger pricks. But after using a glucose monitor, he discovered that leg workouts helped lower his blood sugar throughout the day. He noted that people often stopped focusing on leg exercises as they got older, but it was one of the most helpful exercises for him.