‘Winter House’ Star Kory Keefer Was Almost Cast on ‘Southern Charm’ – and It Destroyed His Friendship With Craig Conover

Kory Keefer from Bravo‘s Winter House revealed he met Naomie Olindo and Shep Rose from Southern Charm during the first season of the show. He said on the Watch What Happens Live After Show that he didn’t like Rose and Olindo “hated” him – but didn’t share that the meeting was during the casting process.

However, close friend Craig Conover, who also stars in Winter House wrote about the meeting and their friendship in his book, “Pillow Talk: What’s Wrong with My Sewing.” He went into detail about how Keefer went through an extensive casting process for Big Brother, only to be kicked to the curb at the last minute. He also wrote about how he and Keefer made a deal to only agree to be on Southern Charm if executive producer Whitney Sudler-Smith cast both of them.

Clearly, Sudler-Smith only cast Conover.

Kory Keefer from ‘Winter House’ joined Craig in ‘Southern Charm’ casting process

Conover knew how rejection from Big Brother stung Keefer. Keefer had gone so far as to quit his job at a local gym and had his bags packed when producers simply didn’t show up to fetch him. So when Sudler-Smith pursued Keefer and Conover for a new show, they took his idea with a grain of salt, especially when all they did was speak to Sudler-Smith.

Kory Keefer, Paige DeSorbo, Craig Conover, Ciara Miller toast during a party at 'Winter House.'
Kory Keefer, Paige DeSorbo, Craig Conover, Ciara Miller | Jude Domski/Bravo

Eventually, Sudler-Smith wanted to see Keefer and Conover on camera. But Conover later learned “that behind the scenes conversations Whitney was having with the actual production company had started to focus on me,” he wrote.

But Sudler-Smith told Keefer and Conover, “The network really likes you guys,” Conover recalled. That’s when Sudler-Smith invited them to a cocktail party with other potential cast members like Rose and Olindo.

Kory reveals why Naomie Olindo ‘hated’ him

Conover wrote about the party, which is what Keefer recounted on the WWHL After Show. He said Olindo “hated” him. “We had a very start of a rocky situation,” he recalled during his appearance for Winter House. “I met her on the pilot of Southern Charm when we were filming at a plantation house.” Keefer said Olindo hated him because he was rude to a server. But Conover wrote in his book that he and Keefer annoyed Olindo by instantly making up the nickname, “Ponytail” and shouting it at her.

On WWHL, host Andy Cohen asked Conover if Keefer knew Rose. “He hated Shep,” Conover said. Keefer added that later Rose would hit on his girlfriend when he and Conover lived together. “He was being aggressive so I kicked him out of the house,” Keefer recalled.

After the party, Conover wrote about how Southern Charm producers continued to pursue him, but not Keefer. “Kory knew what was happening as well,” Conover wrote. Adding that he didn’t want to appear jealous as Conover decided to go for being on the show despite their pact.

Craig and Kory’s pre-‘Winter House’ friendship crashed and burned

Cracks began to form in Keefer and Conover’s friendship, which he said had hardly anything to do with Southern Charm. “A separation had set in,” he wrote. “And it led to several arguments between us, often late at night when he and I had had too much to drink. We’d argue, pass out, then wake up as though nothing had happened. Kory later told me that he thought things might have been different if we hadn’t lived together. I see his point. Our closeness, our bond, so long a source of joy between us, had suddenly become the thing that was driving us apart.”


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Conover wrote about how the show was not the true reason for their “growing estrangement,” but it was the moment when their friendship began to crumble. “We were drifting apart as friends, and the show provided the final slice to sever us entirely,” he wrote.

Eventually, producers told Keefer they didn’t cast him because he was “too young.” Keefer asked producers what he could do to change their minds but their decision was made. Conover was in and Keefer was out. Conover and Keefer continued to live together but their fights became worse and they started avoiding each other. Keefer finally moved out.

“When my best friend walked away, our friendship ended then and there,” Conover wrote. “And I would talk to him again for several years.”