Southern Charm season 10 released its latest episode on February 13, 2025, which saw Shep Rose left hanging at the airport when his then-girlfriend Sienna Evans didn't show up to greet him in the Bahamas. This was followed by the Southern Charm After Show where Shep reflected on his feelings at the time. He felt frustrated, thinking Sienna was playing games with him.
“This is my life, and this is my soul or whatever you wanna call it. And I was just like, ‘You're playing games here. Like, I should be driving this bus. I’m not trying to rock the boat. I understand that there's trouble in paradise, but I got quite angry about it," expressed Shep.
Shep Rose believed they were headed for a serious relationship. Shep said he had big plans for them, including a family trip to Italy. They were supposed to see Coldplay in Milan and then meet his family in Positano. Shep thought this was a clear sign of commitment, and Sienna's behavior confused him.
Southern Charm star Shep Rose's relationship drama amid Molly's confession
Shep's castmate and friend, Craig, was under the impression that Shep and his girlfriend were "very serious like exclusive, and dating." That's what Shep had led him to believe. But when Craig found out they had only met six times, he felt misled. Despite his doubts, Craig still wanted to meet her.
He, Austen, and Shep had champagne ready to celebrate. However, when Sienna arrived, the atmosphere became tense. Craig immediately sensed that something was off. He didn't see any connection or chemistry between Sienna and Shep. It seemed clear to Craig that Sienna wasn't interested in Shep.
“She walks in the room and it just was not… unfortunately, I knew instantly that it was disingenuous,” claimed Craig.
Craig further shared his thoughts on Shep's relationship with Sienna. He believed Shep was trying to recapture the happiness he felt with his ex, Taylor. Shep had met Sienna and thought she could be the one to bring him that joy again. At first, Craig Conover was supportive of the relationship. He was excited when Shep told him they were going to the Bahamas to meet Sienna.
Southern Charm star Craig wanted Shep to give Sienna a chance, despite the challenges of a long-distance relationship. However, Craig's optimism faded when he saw how Sienna treated Shep. She had traveled to South Africa and Cuba without contacting Shep, and then failed to greet him at the airport in the Bahamas.
Meanwhile, Shep also shared his thoughts on Molly O'Connell's crush on him as it was revealed in the latest episode of Southern Charm season 10. He had heard rumors that Molly was interested in him, but he didn't think much of it since they had been friends for over 10 years. Molly had previously dated Whitney Sudler-Smith and had even set Shep up with one of her friends after his breakup with Taylor Ann Green.
Shep explained in the After Show that he didn't think Molly had romantic feelings for him at the time. Shep was dating Sienna Evans, and things were already complicated. Despite this, Shep admitted that he was drawn to Molly's honesty. He appreciated her straightforward nature and genuine personality.
Molly O'Connell shared her thoughts on why she's drawn to Shep Rose. She said that she likes that two of them are tall and would have cute kids. Beyond admiring Shep's physical appearance, Molly always found his morals and intelligence attractive.
"I've always thought Shep's a super handsome guy and is very smart," she explained. Intelligence is very attractive to me," expressed Molly.
However, Molly acknowledged Shep's past mistakes, like cheating on Taylor, but claimed on Southern Charm After Show that she hasn't been perfect in her past relationships either. She added that Shep is exactly what she's looking for but despite living in the same city for years, nothing romantic ever happened between them.
Catch new episodes of Southern Charm on Bravo as they air on Thursdays at 8 pm ET and the next day on Peacock.