There's trouble in paradise for Shep Rose on Southern Charm.
After the cast flew down to the Bahamas for a group getaway designed to reunite Shep with then-girlfriend Sienna Evans, nothing went the way he expected it to.
From a less-than-enthusiastic reunion to an awkward conversation about their future, it was bump after bump in relationship road. Sienna even told his friends at dinner (while Shep was at the bar with Austen Kroll) that she didn't really think of them as exclusive.
Then, as seen in a preview for Southern Charm Season 10, Episode 12, Shep opened up to Madison LeCroy about how he started thinking he and Sienna weren't meant to be.
Shep Rose reveals Sienna Evans wanted $10M house
During the Bahamas boat excursion, Shep talked to Madison about a conversation he had with Sienna while they were visiting a similar location.
"Sienna and I, we went around that point," he described in the preview clip, "And she was like, 'I want you to buy me that house.'"
"Shut up," Madison gasped in response.
"And it was like, a 10 million dollar house. I was like ..." Shep trailed off.
"Do you feel like," Madison asked cautiously, "maybe you're not rich enough for her?"
"Maybe, yeah," admitted Shep.
Shep reveals insecurities about dating and Sienna
It turns out that Shep's experience dating Sienna left him asking some major questions about his own behavior in previous relationships.
"Maybe I don't even deserve this s--t," he told Madison. "Like, who am I? Who the f--k am I? I'm a f--king wild son of a bitch, a sort of disaster zone, and like, how am I a good idea for anyone?"
He elaborated more on these concerns in a confessional.
"I'm realizing that in the past, I was a wild man from hell, and how much stress that put on my relationships, so I'm feeling a bit inadequate. Because a lot of girls are seeking 'stable,' and I'm like Mr. Toad's Wild Ride,'" he admitted.
Back on the boat, Madison heard Shep out — but didn't let him wallow.
"Listen," she told him, "You deserve to be loved as much as you're giving."
This sentiment clearly moved Shep, and it was one Madison repeated again in her own confessional.
"Everybody deserves to be with someone who loves them. Even Shep," she stated. "Honestly, my heart is breaking for him, 'cause it's very clear that he's sad."
Is there anything sadder than being heartbroken on a boat in the Bahamas?
