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The Kelly Clarkson Show - Season 2

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Sherri Shepherd says dating as a comedian is no joke.

During a conversation with guest co-host and comedian Cocoa Brown on Shepherd’s podcast Two Funny Mamas (which she hosts with Kym Whitley), the two talked about how complicated the dating game is for them with Brown saying, “People think you always want to be funny.” And if that’s not the case, then guys they encounter want to prove that they’re funny. Both women also noted that there is a belief that women comedians, because they’re funny, aren’t as feminine.

One especially interesting tidbit though from their conversation was encountering men who either wanted them to be just like they are on stage at all times, or in contrast, wanted to change the ladies because their personalities were so big. The latter was the case for Shepherd. She met a guy at a comedy show and they dated for a year.

“It was a horrible year,” she said. “‘Cause then he kept saying, ‘Why are you so loud all the time?’ When you met me I was loud. I was on stage killing. Then he was like, ‘Why you tell all your business on stage?’ He was..aw girl. It was the worst year.”

The fact that Shepherd could easily be the center of attention even when off the stage also became a problem for her ex-boyfriend.

“He didn’t get it. He didn’t get it. Like, ‘Why did we have to, when you go in the room it’s like you’re the life of the party.’ When you met me I was on stage” she said of his issues.

The star has been married twice, to Jeff Tarpley from 2001 to 2009 with whom she shares son Jeffrey, and Lamar Sally from 2011 to 2014. She pays both men child support — Sally for a child conceived via a donor egg and surrogate during their marriage. She’s said that she picked them and accepted the “consequences of bad choices” when looking for Mr. Right, but none of that has stopped her from wanting to find love again.

“I’m single and I’m open,” she said back in 2018. “I’ve been single for about four years. I think I’m ready to put my feet into the dating pool. The water’s a little cold, but I think I’m ready. Don’t send me none of your uncles. I need people with their own teeth, their own knees. Good credit. Maybe they own their own home. You know, I got a lot of little factors, but I think I’m ready to date.”

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