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Kelsea Ballerini recalls bidding on date with Craig Conover on ‘Southern Charm

Kelsea Ballerini, seen here in January 2025, said she is still haunted by her bidding on a date with Craig Conover at a charity event in 2014. Getty Images

Kelsea Ballerini recalled bidding on a date with Craig Conover at a charity auction during Season 2 of “Southern Charm” in 2014.

“Oh god, it haunts me forever,” the singer admitted after being asked about her brief cameo on the Bravo show during Tuesday’s Cosmopolitan’s “Cheap Shots.”

After noting that she did not bid her own money for the date, she told the outlet that she wanted to “clear this up” and tell fans what really happened.

The singer recalled bidding on the date with Conover on Season 2 of “Southern Charm” during an interview with Cosmopolitan published Tuesday. caconover/Instagram
“Oh god, it haunts me forever,” Ballerini said. kelseaballerini/Instagram

“I was on [a] radio tour and I was doing a show for the radio station on a boat and they were filming ‘Southern Charm’ on the boat,” Ballerini, who was an up-and-coming star at the time, recalled.

The 31-year-old pointed out that she didn’t know the cameras were rolling because she was just focused on performing her song “Love Me Like You Mean It” so the radio station would play her music.

“Little did I know, my publicist set up the fact that I was going to bid on a date. I didn’t know,” she said. “I get pushed into the [camera] frame … bid it, got the date.”

Despite the big theatrics over the date, Ballerini didn’t actually get to be wined and dined by the By The Way co-owner.

The “Cowboys Cry Too” artist said she was at the event to perform for a radio station when she was forced in front of Bravo cameras. kelseaballerini/Instagram
“I get pushed into the [camera] frame … bid it, got the date,” she recalled. Bravo

“They auctioned [the date] off on the radio station for charity,” she said. “Some winner from the radio station got it.”

When asked if she was better off for not going on the date, she replied with a laugh, “Yeah, everything is great as it turned out.”

Years after the embarrassing fundraiser unfolded, Ballerini found love with Morgan Evans and they tied the knot in 2017. Unfortunately, things didn’t last and they split up in August 2022, settling their divorce three months later.

She moved on with “Outer Banks” star Chase Stokes in 2023 and they appear to be going strong.

She is currently dating Chase Stokes, seen here at the 2025 Grammys. Kevin Mazur/Getty Images for The Recording Academy
Conover dated Paige DeSorbo for three years before announcing their breakup in December 2024. Variety via Getty Images

Conover, for his part, started dating “Summer House” star Paige DeSorbo in 2021.

Despite talking about getting married and starting a family together, the “Giggly Squad” co-host revealed in December that she and Conover, 36, had ended their three-year relationship.

“I love him. I think he loves me. I think we will remain friends,” the 32-year-old shared on her podcast at the time.

“No one did anything. It wasn’t a bad thing. I think we both were just being really mature and saying what we want and what we didn’t want, and I think that’s extremely powerful to be able to voice how you’re feeling in real time and what you want for your future.”

The “Summer House” star said that they ended on good terms. Instagram/paige_desorbo
Conover said he was blindsided by their breakup.

Conover, for his part, claimed their breakup was not mutual and “came out of nowhere.”

“We didn’t want different things –– she just wanted other people, and that’s fine,” he claimed on “Watch What Happens Live with Andy Cohen” earlier this month.

“Like, she didn’t want those things with me anymore, and, like, I’m not mad at her for that, but I don’t like this, ‘Love isn’t enough thing,’ because, you’ll make it work.”

The now-exes had struggled with being in a long-distance relationship, with DeSorbo living in New York City and Conover being based in Charleston, S.C.



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