After a season of questions around Sienna Evans’ real relationship with Shep Rose on Southern Charm, rumors have come out that Sienna had an alleged boyfriend while she was still dating Shep—and he’s a multi-millionaire.
Who was Sienna’s boyfriend during Southern Charm?
Sienna’s Southern Charm cast claimed that she was dating an NFL player while she was seeing Shep, which is why she was fast to deny that they were in love and in an exclusive relationship.
“We found out after filming wrapped that [Sienna] was seeing someone,” Shep’s ex-girlfriend Taylor Ann Green said. “While we were all in the Bahamas, she was seeing some football player,” to which Rodrigo Reyes responded that Sienna “pulled a Shep on Shep.” Taylor, who had been cheated on by Shep, added “Medicine doesn’t taste too good, does it?”
Molly O’Connell also confirmed the rumor. “She was like, ‘Oh, I got another boyfriend from the NFL on the back-burner, so yuck,’” she said.
While none of the Southern Charm cast gave a name for Sienna’s NFL boyfriend, Craig Conover revealed during the aftershow that Sienna left Shep for a Denver Broncos player. “These fans just came up to me and said [Shep] found them in a bar in Kansas City a couple of weeks ago, and, like, all he talked about was her. 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,” Craig said.
Shep, for his part, also seemingly accused Sienna of dating the NFL player for his money, while adding that Sienna’s sister, Anissa Evans, has a child with Portland Trail Blazers player Deandre Ayton.
“He makes $35 million a year, or $25 [million], whatever,” Shep said of Sienna’s NFL boyfriend, to which Austin Kroll asked, “So you have fond memories, but you are wholeheartedly calling her a gold digger?” Shep responded, “I know what happened. If she was like, ‘I hacked his bank account, and there’s a few mil short of what I require?,’ that basically would have been as honest a thing that she could have said.”
During an episode of the podcast, “Two Ts in a Pod,” in January 2025, Shep seemingly accused Sienna of using him for his money. “We took a little break because of something that happened,” he said. “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.”
Shep went on to reveal that he invited Sienna and her friend to visit him, however, the day before Sienna was set to arrive, she told Shep she hadn’t bought the 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 said. “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 claimed that Sienna told him, Shep said Sienna told him, “Where I come from, the man takes care of everything.” He added, “That’s a bad thing to think and to practice, frankly. So anyhow, I was like, maybe we should take a step back, and she was like, ‘Yeah, OK.’”
Southern Charm streams on Peacock.
