Craig Conover and Taylor Ann Green revealed new insight on Shep Rose's breakup with Sienna Evans on the Southern Charm After Show.
Though Shep Rose and then-girlfriend Sienna Evans’ breakup in the Bahamas on Southern Charm Season 10, Episode 13 seemed to come as a surprise to nobody — except Shep, of course — a more shocking detail emerged after the cameras stopped rolling, according to his fellow cast members.
“We found out after filming wrapped that [Sienna] was seeing someone,” Taylor Ann Green revealed in the Southern Charm After Show video above. “While we were all in the Bahamas, she was seeing some football player.”
Added Molly O’Connell, “She was like, ‘Oh, I got another boyfriend from the NFL on the back-burner, so yuck.’”
The Southern Charm cast reacts to Sienna Evans' alleged secret relationship
Naturally, Shep’s castmates had thoughts.
“She pulled a Shep on Shep,” Rodrigo Reyes joked on the After Show, citing his fellow cast member’s past infidelity.
Taylor, who had previously been on the receiving end of Shep’s cheating, chimed in, “Medicine doesn’t taste too good, does it?”
Craig Conover, for his part, didn't hold back while speculating about Sienna’s motives for going along with the relationship: “She was like, ‘Hey, this simp who’s on this kinda cool show wants me to come hang with him. Like, I’ll do it.”
How is Shep Rose handling his split from Sienna Evans?
Though the Bahamas breakup happened quite some time ago, Craig shared a story on the After Show that indicated that Shep is still far from over Sienna.
“These fans just came up to me and said he found them in a bar in Kansas City a couple of weeks ago, and, like, all he talked about was her,” Craig spilled. “Because, like, the Broncos were on TV, and he was like, ‘Can you believe she left me for the Denver Broncos?’ And he was like showing them texts, and I was like, ‘Oh god, Shep you’re still down bad? This was like a year ago.'”
Meanwhile, Shep — who’d already admitted to feeling inadequate and questioned if he was “rich enough” for Sienna — seemed to think her dating someone with an NFL star’s salary might have validated his financial insecurities.
“What if she was like, ‘I hacked his bank account and there’s a few mil short of what I require’?” he asked Austen Kroll in the After Show clip. “That basically would have been as honest a thing that . . . she could have said.”
Why did Shep Rose and Sienna Evans break up?
Shep confirmed his split from Sienna at Bravo Fan Fest in November 2024. Although Southern Charm viewers saw their relationship end on the March 6 episode, Shep previously revealed that the pair had taken a break prior to their Bahamas conversation.
“We took a little break because of something that happened,” he said on a January episode of Two Ts in a Pod. “I’ll tell you exactly. So I bought her her flight to Hilton Head and Charleston, the first two trips, and I was happy to do it, right? Then I went down to Nassau and she was very generous. She got me a hotel room at the Baha Mar and, boy, we had fun. The Bahamas was amazing.”
Shortly after, Shep invited Sienna and her friend to visit him, but just a day before Sienna was expected to land in the U.S., she allegedly told Shep she hadn't purchased a plane ticket.
“She was like, ‘Hey, I’ve been really busy. Will you just get my flights?’ … I said yeah, OK, and I bottled it up,” Shep stated. “And then after the weekend, I said something to her… I said, ‘I really need to get this off my chest… I just don’t appreciate the way that was handled. I made a lot of plans and I took care of everything... Just meet me somewhere in the middle or near the bell curve somewhere, because I’m not a desperate man who’s flying girls around.'”
Shep said Sienna told him, “Where I come from, the man takes care of everything.” With that, Shep revealed he questioned if Sienna would repeat that sentiment to the young girls she mentors.
“That’s a bad thing to think and to practice, frankly,” he continued. “So anyhow, I was like, maybe we should take a step back, and she was like, ‘Yeah, OK.’”
Watch the After Show above and don’t miss what Shep had to say about why he thought Sienna was “playing games” in the Bahamas here.
