Kelsea Ballerini Recalls Winning a ‘Date’ with Craig Conover and Says Southern Charm Appearance “Haunts” Her, Plus Reveals Why She Bid for Him

Singer Kelsea Ballerini addressed winning a ‘date’ with Craig Conover at a charity auction 10 years ago on Southern Charm, and she revealed why she bid for him. Craig was single at the time, and a few months ago, he got out of a three-year relationship with Summer House star Paige DeSorbo.

In May 2015, Kelsea appeared in an episode as Patricia Altschul ‘auctioned’ off Craig and castmate Shep Rose for a charity event. At the time, Kelsea hadn’t reached the level of fame she has now. In August 2022, she filed for divorce from Morgan Evans, another country singer. Five months later, she started dating actor Chase Stokes from Outer Banks.

Playing a “Cheap Shots” game for Cosmopolitan, Kelsea addressed Craig’s auction date from the 2015 episode.

“It haunts me forever,” said the singer, who shared that she can’t “remember” the amount she bid on him. Kelsea shared that she was only there for a radio gig to perform and promote her songs.

“I was on [a] radio tour, and I was doing a show for the radio station on a boat. They were filming Southern Charm on the boat. I didn’t know that,” said Kelsea. “I was just there playing ‘Love Me Like You Meant It.’ Being like, ‘Hey, radio station, please play my song.’”

“Little did I know my label had set up the fact that I was going to bid on a date,’ the singer went on. “I didn’t know.”

She ultimately bid on Craig and “got the date” after being “pushed into frame.” According to Us Weekly, she bid $5,001.

Kelsea said they never had their date because they “auctioned it off on the radio station for charity,” and the winner hung out with Craig.

A staff member at Cosmopolitan said, “You’re probably better off.”

Kelsea laughed, “Everything’s great as it turned out.”

At the time, Craig shared on camera that he was surprised by the bid. “I did not expect Kelsea Ballerini to bid on me,” he said. “I was worried about the auction because I was like, ‘Oh, shoot, I hope it’s not some, like, weirdo or creepy person.’”

When Kelsea ‘won,’ she and Craig embraced in front of the crowd.

“At this moment, I’m dying,” Craig recalled in another scene. “Like, I am so happy on the inside. I’m giddy as hell.”

Shep shared his disappointment about Craig getting the ‘date’ with Kelsea. “It’s not fair. She’s a singer,” said Shep, who added that she’ll be “underwhelmed” by the date with Craig.