“Southern Charm” star Craig Conover is sharing the advice he gave his castmate Shep Rose about his relationship with his now ex-girlfriend, Sienna Evans.
In the February 13 episode of the “Southern Charm After Show,” Conover said he understood Rose’s dynamic with Evans, who lives in the Bahamas, as he and his ex-girlfriend, Paige DeSorbo, were also in a long-distance relationship. Conover and DeSorbo ended their relationship in November 2024 after three years of dating.
According to Conover, he told Rose “to give [Evans] the benefit of the doubt.” He said that Austen Kroll had advised Rose to “stop talking to her” because of her lack of communication.
“I was like look, ‘Long distance is hard. You have to trust each other. And you can’t let your deepest insecurities run the roost,'” said Conover.
Conover also said that while he does not think Evans “was a bad person,” she did not seem to have a genuine connection to Rose.
Austen Kroll & Craig Conover Shared Their Theories About Shep Rose’s Relationship With Sienna Evans
During the February 13 “Southern Charm After Show” episode, Conover shared his theory about Rose’s relationship with Evans. He said he believed Rose wanted a romance similar to what he had with Taylor Ann Green. The former couple broke up in 2022 after two years of dating.
“My theory the whole time was he has never been as happy as he was when he was with Taylor. And he’s chasing that relationship. Like he wants that feeling again. And he met a girl that he felt could work in his head. And he was like, ‘I need this to work to be happy again,'” said Conover.
Kroll shared he had a similar theory about Rose and Evans in a January 2025 interview on the “Chicks in the Office” podcast.
“Shep had this relationship with Taylor and I think it was the first time in his life that he really had someone like he loved and cared about. And he had a partner. He messed up. And they broke up. But I think he wanted that since. So I think he found that girl, and he wanted a connection again so bad that he was like ‘Maybe it’s supposed to be with her.’ So he kind of dove into this thing,” said Kroll during the interview.
Shep Rose Spoke About His Breakup With Sienna Evans
During a January 2025 episode of the “Two Ts In A Pod” podcast, Rose said he is currently single.
Rose also said he and Evans had a “very much loving” relationship, despite their breakup, in a December 2025 interview with Access Hollywood. He also said that his split from Evans was “humbling.”
