Long before Craig Conover began dating Paige DeSorbo or Naomie Olindo, he was auctioned off at a charity event to have a date with country music star Kelsea Ballerini.

The moment took place on Season 2, Episode 11 of Southern Charm (which was also the finale episode, and it originally aired in 2015). Patricia Altschul planned a charity event in honor of Wounded Warriors, and she auctioned off dates with Craig and Shep Rose.

When it was time for Craig to hit the stage, the “Miss Me More” singer offered to pay $5,001 for a date out with Craig.

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“I did not expect Kelsea Ballerini to bid on me,” Craig admitted in an interview on the episode. “I was worried about the auction because I was like, ‘Oh, shoot, I hope it’s not some like weirdo or creepy person.”

After Kelsea won, Craig went up to her and the two embraced.

“At this moment, I’m dying,” the Sewing Down South founder said in another interview on the episode. “Like, I am so happy on the inside. I’m giddy as hell.”

Craig was happy, but Shep wasn’t.

“He went first, it’s not fair!” Shep lamented. “It’s not fair. She’s a singer.”

In his own interview, Shep said that Kelsea would be “underwhelmed” by her date with Craig.

When it was time for Shep to go, he was only able to bring in $1,750 — and it was his castmate, Cameran Wimberly, who made the bid. Craig and Shep later argued about the result of the auction.

 

Did Craig Conover and Kelsea Ballerini ever go on a date?

Though Kelsea paid a pretty penny to take Craig out, the two never went out on a date together. Instead, she gave the date away to a radio station to offer out as a prize.

Kelsea Ballerini laughing in a crowd.

Kelsea Ballerini laughing in a crowd.

Who is Craig Conover dating now?

Though Craig’s date with Kelsea never materialized, he wasn’t totally out of luck in the love department. He went on to date Southern Charm alum Naomie from 2015 to 2017, and he’s been in a relationship with Paige since 2021.

Kelsea has also had some developments in her love life. She was married to fellow country singer Morgan Evans from 2017 until 2022. Since 2023, she’s been in a relationship with Outer Banks actor Chase Stokes.

Watch Southern Charm on Thursdays at 9/8c on Bravo. Stream episodes the next day on Peacock.