Southern Charm’s Craig Conover Shares Theory on Why Shep Was Infatuated With Sienna, Shades Her as “Disingenuous” as Madison & Austen Weigh in, Plus Shep Speaks

Craig Conover believes he knows why Shep Rose was so infatuated with Sienna Evans amid the 10th season of Southern Charm — and Austen Kroll agrees.

Following a recent episode of the show, which saw the cast arriving in the Bahamas for a visit with Sienna, 26, Craig, 36, admitted to feeling “misled” about Shep, 44, and Sienna’s relationship and labeled her “disingenuous” as Madison LeCroy, 34, recalled Shep’s plan to settle down with the pageant queen and Shep suggested Sienna wasn’t being honest and open.

“Shep was so infatuated with Sienna that it was hard for him to pay attention to anything else,” Craig began on the recent episode of the Southern Charm: After Show. “My theory the whole time was he has never been as happy as he was when he was with [Taylor Ann Green] and he’s chasing that relationship. Like, he wants that relationship. He wants that feeling again.”

Looking back on the cast’s trip, Craig said he went into the vacation with the idea that Shep and Sienna were “very serious” and dating exclusively — only to later learn that the duo had seen one another just “six times.”

“I was like, ‘Okay, I feel very misled,'” he recalled.

“That’s wild to me,” Madison replied. “He’s like, I’m having kids, I’m gonna marry this girl and I’m gonna buy a house in the Bahamas.”

According to Craig, Madison was “always suspicious” of Sienna and he felt it was odd that Shep was comparing his relationship with Sienna to that of him and his now-ex-girlfriend, Paige DeSorbo, 32.

“I was like, we spend every week together. You’ve seen her six times.’ But I wanted to meet her,” he admitted.

But after being introduced to Sienna, Craig immediately found her to be “disingenuous.”

“I knew instantly it was disingenuous. I could just tell that like, there was zero connection or energy or chemistry between her and Shep [and] she wasn’t there because she liked Shep,” he explained of Sienna’s alleged ulterior motives. “It wasn’t that she was a bad person, it was just that she was not into Shep and it felt so awkward to be there.”

And Austen felt equally awkward. 

“When she got there, [there] was so much tension in the room,” he shared.

Meanwhile, Shep said he “didn’t feel that.”

“But again, my head was probably spinning,” he noted.

As Shep explained, he was “trying to rock the boat” in the Bahamas, even though he was “quite angry” about the way Sienna behaved.

“She was supposed to come with my whole family to Italy. We were gonna go see Coldplay in Milan and then go meet my family… Is that not a relationship? Who makes that plan?” he wondered. “She was so excited about having us down. She was gonna meet with the tourism board, ‘I can’t wait to see you,’ it was gonna be like a coronation of our relationship and like that it was like, poof…”

Looking back, Shep said that Sienna called him a week before their trip and said they needed to “have a conversation.”

“I was like, ‘I agree but we’re gonna have it on camera. This is my life, This is what I do. You knew that. You came on tv, you were cool with that,’” he stated. “The audience, I respect them and I want them to see the real, honest, raw things that go down. And the way I do that is to be completely honest and open … She was being opaque.”

Agreeing with Craig’s sentiments regarding Shep’s infatuation with Sienna, Austen said it was “very obvious” that he was hunting for something meaningful, like what he had with Taylor.

“You wanted that feeling again because you really liked having a person in your life like that,” he told Shep.

And Shep didn’t disagree.

“I called Taylor every day all the time … and when that’s over, it’s jarring, I would say. Forget about doing everything together and kissing and hugging and stuff, that’s the part that’s tough,” he confessed.

Southern Charm season 10 airs Thursdays at 9/8c on Bravo.