Shannon Sharpe and Sheryl Underwood have been friends for a long time, and the duo has recently reminisced about their first date. Underwood was a guest on Sharpe’s Club Shay Shay podcast, published on January 22, 2025. During the show, they discussed Underwood’s journey as a comedian and their first encounter. The longtime friends shared many heart laughs as they recollected the memories of their failed date during their first meeting.
Shannon Sharpe and Sheryl Underwood Discuss Longtime Friendship
It helped that Shannon Sharpe and Sheryl Underwood have been friends for over three decades, as they had an interesting conversation on the latest episode of Sharpe’s podcast. During the interview, the pair broke off into a discussion about when and how they met. Underwood recollected that they met during one of her shows and said:
“When you came on the tour, you walking out with the flowers looking all dashing, and I was like, ‘This is the same dude I was trying to pull in 1993 in Denver.'”
After the NFL star affirmed it, she asked him to recount what happened. Sharpe acquiesced and said he first saw his friend on Death Comedy on Comic View in 1992. When he heard about her performing in Denver in 1993, he and some teammates visited her. After the show, Sharpe went backstage and introduced himself. However, Underwood already knew who he was and was excited to see him. Thus began an over three-decade-long friendship that continues to blossom to date between the two.
Shannon Sharpe and Sheryl Underwood Had a Failed Date
Before Shannon Sharpe and Sheryl Underwood settled for being friends, the two had a date that didn’t end as it should. Sharpe revealed that he had taken Underwood back to her hotel, and they had talked until they reached their destination. However, their meeting didn’t end after the ride, as Underwood had one request for the podcast host. After they got to the hotel, Sharpe asked the comedian what she wanted to do.
“I thought to myself, you know, what would any other woman want to do?” Underwood recalled.
“I said, I would like to go on the carriage ride. You said I will take you. I said, hold on, let me finish selling these CDs. These tapes, these cassette tapes. Remember that? …So then we get in the car, can’t find the carriage ride, so we talking and we talk all night long,” she disclosed.
Shannon Sharpe and Sheryl Underwood talked for about two hours that night, exchanged numbers, and have remained good friends ever since. Sharpe said:
“Every time if I’m somewhere and she’s there, we’re gonna find a way to connect.”
Sheryl Underwood Won’t “Shack Up” a Man With Daughters
During Shannon Sharpe and Sheryl Underwood’s conversation, Sharpe also brought up an interesting topic. He asked his friend, who had lost her husband, if she believed in marriage. The Talk co-host said she did. However, when Sharpe asked if she was open to living with a man she was not married to, Underwood immediately shot down the idea.
“Can’t no man worth his manhood and his backbone put his key in anything I own and walk in like he run it, or he own it. You are not a man,” she argued.
The 61-year-old actress added that her stance would be stronger, particularly when the man has female children.
“No, I can’t shack with no man, especially if you have children. And you got daughters? I’m not going to show your daughters how to be whores; I’m not doing it,” she said.
Meanwhile, Underwood clarified that she is interested in getting married again but is not officially in a relationship.
Shannon Sharpe and Sheryl Underwood’s friendship, which has lasted this long, is beautiful to see. Hopefully, the duo will continue making happy memories.
#Clique, what do you think of Shannon Sharpe and Sheryl Underwood’s friendship? Let us know in the comments.
