Shep Rose Talks Relationship Doubts with Sienna Before Their Split: ‘Your Mind Can Play Tricks’

On Southern Charm Season 10, Shep Rose's relationship with Miss Bahamas World Sienna Evans is fresh, but Shep is smitten — and navigating the challenges of falling hard for someone in a long-distance relationship.

On Episode 8 of the season, Shep opened up to Austen Kroll and Craig Conover about struggling without being in constant contact with Sienna. He expanded on that in a confessional during Episode 9, which aired on February 6. 

"I think I was 24 the last time I felt this unsure of myself and twisted up about somebody," he admitted. 

Navigating the nuances of dating someone who lived in another county had been an ongoing challenge. Plus, Sienna's evasive answers during their FaceTime conversation about his upcoming trip to the Bahamas weren't exactly reassuring.

"I'm not an insecure person, thank goodness," Shep said, "But I thought I wanted somebody who is my peer, and then have an equal balance of power, right? But she might be up here," he explained, motioning one hand above the other, "and I don't like it one bit."

"When you're really into somebody, your mind can play tricks on you," he continued, "And I thought I was done with all that."

After declaring, "You have to train yourself sometimes," Shep added, "You just have to operate on faith at that point, but your faith is easily tested."

The perceived emotional distance between the two, not to mention Sienna being in another country, had been a new experience for him. Previously, the longest relationship fans had seen Shep part of on Southern Charm was with Taylor Ann Green, who is now dating Gaston Rojas.