The Southern Charm-er had to witness the demise of Shep and Sienna's romance when they traveled to the Bahamas.
In Season 10, Episode 13 of Southern Charm, Shep Rose's romance with Sienna Evans came to an unexpected end — at least from his point of view. After pouring his heart out to Sienna over text and on the beach, Shep was ultimately left brokenhearted and confused as to why his feelings weren't being reciprocated.
But based on the snippets she heard from Shep, Madison LeCroy said on the Southern Charm After Show that she thinks Sienna expected a more lavish lifestyle with the Charleston man. Instead, the former Miss Bahamas got gifts like a shark tooth necklace.
"[She] thought it was going to be a Birkin bag, dummy," she joked.
While Shep may be wealthy thanks to his mailbox money, that doesn't mean he's splashing out on jewelry and purses for his girlfriends. In fact, Madison and Craig Conover both said he's actually pretty "cheap."
Shep himself acknowledged that he may not have a big enough wallet for Sienna, with Madison revealing, "He had made comments that like, she wanted a mansion and she wanted a house on the water and she wanted to fly first class and all these things and he was like, 'No, I'm not doing that.' So maybe that's what turned her off."
Shep said dating Sienna made him feel "inadequate"
Madison's theory largely stems from a conversation that she had with Shep when the cast went out boating during their vacation in the Bahamas, as shown on Season 10, Episode 12. In that moment, Shep shared that he and Sienna had taken a similar boat ride in the area "and she was like, 'I want you to buy me that house.'"
The house in question "was like, a 10 million-dollar house," according to Shep.
And though he previously ignored all signs that there was trouble in paradise, Shep admitted that it made him wonder if their relationship wasn't meant for the long haul. More than that, it made him question if he was even suited for a committed relationship.
"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?"
Shep might have a rocky relationship history, but even Madison said that Shep deserves love. "Everybody deserves to be with someone who loves them. Even Shep," she shared in a confessional.
Shep asks fans to "take it easy" on Sienna
Though Shep was heartbroken after Sienna basically dumped him in the Bahamas, he told fans to "take it easy" on her in a Feb. 21 Instagram Story.
"We had some wonderful times together," he wrote. "Things happen the way they should."
To find out what else the Southern Charm-er had to say about spilling his heart to Sienna on TV, read more here.
