Shep Rose fell hard for Sienna Evans after only dating for a couple of months — but their romance was short-lived.
“I met Sienna on a dating platform, and I was immediately captivated by her,” Rose shared in a segment of Southern Charm in December 2024. “I just find her incredibly attractive.”
The couple, who sparked a romance in early 2024, dated long-distance for the duration of their romance and before calling it quits that fall.
After their relationship hit a rough patch, Rose recounted a significant argument they had. It all started when Rose bought two tickets for Miss Bahamas to visit Charleston. As Sienna was preparing for her third trip, Rose was dismayed to discover that Sienna, who was 26 at the time, had not yet arranged her flight.
“She told me, ‘I’ve been really busy. Can you handle booking my flights?’ … I agreed, but deep down, I was holding onto my feelings,” Rose explained in a December 2024 interview on the “Two Ts in a Pod” podcast. “After the weekend, I decided to confront her… I told her, ‘I need to talk about this… I didn’t like the way it was handled.’”
He noted, “I made a lot of plans and I took care of everything” and asked her to “meet me somewhere in the middle.” Rose pointed out he was “not a desperate man who’s flying girls around.”
Evans allegedly responded, “Where I come from, the man takes care of everything,” which led to a brief split. The twosome eventually reconnected before calling it quits for good.
Scroll down to see Rose and Evans’ whirlwind romance from the start:
January 2024
Eagle-eyed fans noticed that Shep started to comment on Evans’ social media posts in the new year. “Love grows,” Evans captioned a photo of roses blooming on January 7.
“I’ve never heard that song before in my life. But it has my last name in it. So I’ll support,” Rose replied, referring to Edison Lighthouse’s full song title, “Love Grows (Where My Rosemary Goes)” from their 1970 hit.
Evans cheekily wrote back in the Instagram comments, “‘You’re so vain … you probably think this song is about you …’”
March 2024
Rose revealed during a season 10 episode of Southern Charm that he first told Evans he “loved her” when they were in Palm Beach, Florida in March 2024. “I meant it. I felt it,” he said of the big moment.
April 2024
The model met the bulk of Rose’s friends during a visit to Charleston, which was filmed for season 10 of Southern Charm. During her trip, she attended a Doggy Parton birthday bash for Rodrigo Reyes’ pooch.
May 2024
Rose brought his Bravo castmates down to the Bahamas to see Evans while they were dating. The getaway was captured on film for season 10 of the reality show. During the episode, which aired in 2025, Rose revealed he hadn’t seen Evans in person in “over a month and a half.”
November 2024
Rose teased his and Evans’ relationship status at Bravo Fan Fest, saying, “I don’t know if I want to reveal because of Season 10, but I was right there and I got pretty cut down, let’s just say. And it’s all out there for everyone to see, so.”
He seemingly confirmed he was single again, revealing that he was back on the dating app Raya. Rose noted this time around that he upped his minimum dating age to “28 and above,” whereas it used to be 26 years old.
December 2024
Evans made her Southern Charm debut during season 10, episode 2, while on a FaceTime call with Rose. The following episode, Evans showed up in person to attend a dog party in Charleston where she was introduced to his ex Taylor Ann Green. (Green and Rose called it quits in July 2022 after two years of dating.)
“Nice to meet you. I’ve heard so much about you,” Evans told Green in the episode. Green replied, “Oh, thank you. Well, hopefully good things. Were they good?” Evans then responded, “Mostly.”
As Rose and Evans’ relationship played out on the Bravo series, the TV personality got real about his feelings for her pre-split.
“She was a very interesting girl,” Rose revealed during a December 2024 appearance on the “Two Ts in a Pod” podcast. “I really liked talking to her and spending time with her, and we had a lot of very lovely, tender moments, and it was not for nothing. I mean, don’t believe everything you see on TV.”
January 2025
The cracks in Rose and Evans’ relationship became more evident during the January 30 episode of Southern Charm. Rose explained to pal Austen Kroll that after Evans traveled to Africa, she started to ghost him.
“I was kinda spiraling,” Rose explained, noting that when Evans eventually texted him, she said she needed “space.” Rose later confessed, “My fear, my paranoia is there’s some f—ing dude.”
Elsewhere in the episode, Patricia Altschul told Madison LeCroy that Evans approached her son, Whitney Sudler-Smith, before Rose started pursuing her. “It screams ulterior motives to me,” Altschul said of Evans “angles.”
February 2025
Rose admitted during the February 6 episode of the Bravo series that he wasn’t “quite sure” where he and Evans stood. “There’s a part of me that thinks … we kinda remember how much we make each other happy, and we move from there,” Rose said of his hopes for his trip to the Bahamas to see Evans.
Once the group was in the Bahamas, which was highlighted in multiple February episodes, it became clear that Rose was more excited about Evans than she was about him.
“I know where I stand. I don’t know where she stands,” Rose told his friends during the February 13 episode, while Craig Conover and Kroll claimed that Evans was leading Rose on.
When Evans showed up to the resort, Rose told her how much he loved her and missed her, and she didn’t give back the same energy. “I’m wildly, wildly attracted to you and I’m actually in love with you,” Rose confessed. Evans responded, “I feel like we never kinda defined what the relationship was.”
Evans broke her silence about the relationship on February 19, first clearing up Sudler-Smith’s claims that they connected on Raya before Evans met Rose. Evans alleged via TikTok that it was Sudler-Smith who “direct requested” her first.
She explained that it felt like a “total catfish” when she did meet Sudler-Smith in person while visiting Rose in Charleston because she “did not recognize him” based on his photos. It wasn’t until she was stateside with Rose that she allegedly realized they knew each other — or that Sudler-Smith previously messaged her.
Evans also claimed that despite her grandmother being a Southern Charm fan, she didn’t know Rose was on the series when they first connected on Raya. “He messaged me and he was like, ‘Oh, you’re from the Bahamas? I always go to the Bahamas, I love the Bahamas,’” she recalled. “And I was like, ‘Oh, he’s cute,’ or whatever, and that’s how we met. And then he followed me on Instagram and we started talking on Instagram and that’s kind of how things started.”
