Some of the best reality TV shows on Bravo are those where the castmates have depth in their friend group. Friendships that are years long cultivate some of the most intoxicating television — especially when relationships are involved. Like one of Bravo’s most successful reality shows, Vanderpump Rules, Southern Charm has a core group of friends who have been intertwined in each other’s lives for over a decade.

Core members like Shep Rose, Craig Conover, and Whitney Sudler-Smith have been a part of the series since Season 1 and have seen and done it in Charleston. With Charleston being such a small town — and the cast being incredibly attractive — mutual hookups or relationships are bound to happen. And while brief fallouts are inevitable, the friendships typically come out on top.

The Season 10 Cast Have A Deep Past With Each Other

Season 10 of Southern Charm has a great cast after a few shaky seasons. While there are new faces on the Season 10 roster, everyone has known each other or has been involved with each other in one way or another, curating loads of reality TV content.

Over the years, fans have seen the cast members hook up with each other, date each other, and search outside their friend groups. But there are so many faces and names, it can be hard to remember who was with who.

Shep Rose

Shep Rose has been an integral part of the show’s success. A well-read, Southern man, Shep has been with his fair share of women around Charleston. However, now in his 40’s, Shep is looking for a slower pace (but that doesn’t necessarily mean settling down).

• Shep used to “hang out” with former castmate, Chelsea Meissner. The two ended things when she developed feelings for fellow cast member Austen Kroll. This, of course, created tension between Shep and Austen. “Remember Chelsea? She and I were hanging out, I left for that weekend, and [Austen] moved right in,” he said on an episode, according to Bravo.
• In Season 1 of Southern Charm, Shep was in a tangled web with former castmate Kathryn Dennis. In a 2018 Katching Up With Kathryn podcast, Kathryn admitted the two “hooked up” multiple times over the years, as reported by US Weekly.
• While Landon Clements wanted to make a relationship with Shep happen, he admitted he only saw her as a friend despite hooking up when they were friends in college.
• Shep and cast member Taylor Ann Green dated for two years before calling it quits. The two were incredibly serious but Shep’s inability to slow down and commit to Taylor drove them apart.
• New cast mate, Salley Carson, admitted to sleeping with Shep after he and Taylor broke up.
• In the early seasons, Shep was in a complicated relationship with former cast member, Danni Baird.

Craig Conover

Craig Conover is the number one guy in the group, according to Bravo fans. He’s loyal and committed to bettering himself. As of recently, Craig is just getting over his three-year relationship with Summer House star, Paige DeSorbo. However, in the past, he was with two former cast members.

• People reported that Craig and former castmate Naomie Olindo dated for almost three years. The two started dating after meeting in college but broke up when their differences in lifestyles caught up to them. The two briefly hooked up when they found themselves single in 2021, but it never went anywhere serious.
• Craig told the Domenick Nati Show that he never hooked up with another castmate who wasn’t Naomie. However, fans theorize that he spent the night with Kathryn Dennis when the group was on a cast trip. “A lot of people think Kathryn and I hooked up. We’ve actually never even kissed,” he said, per Reality Tea.

Whitney Sudler-Smith

Whitney Sudler-Smith has been in and out of the drama over the years, since he’s one of the creators of Southern Charm and an executive producer. While he keeps most of his relationships off the table so they’re not the focus of the show, he has been with a few cast members.

• In the early seasons, Whitney was head over heels for Kathryn Dennis. However, Kathryn also saw Shep Rose and Thomas Ravenel. With all of them being friends, Whitney was hurt and outbursts between him and the men occurred. Many agree Whitney’s ego was hurt when Kathryn chose Thomas over him, and the two never became more serious.
• In 2022, Naomie Olindo and Whitney admitted they were dating. Naomie told Bravo that their relationship was “a slow build.” The two didn’t date for long, but Naomie’s ex-boyfriend and fellow castmate, Craig Conover, found the relationship to be odd, stating Whitney broke “bro code.”
• In Season 10, new cast member Molly O’Connell admitted that she and Whitney had an on-again, off-again fling for years. Although they were never serious, the season shows that Molly has feelings for him.

Austen Kroll

Austen Kroll joined the series in Season 4 as one of Shep Rose’s old friends. A competition soon began between Shep and Austen when it came to the women who admired both of them.

• Madison LeCroy was one of Austen’s most serious relationships. She was already friendly with members of the show as she was Patricia Altschul’s hair stylist. The two eventually broke up after being on and off for three years.
• Austen dated former cast member Chelsea Meissner in Seasons 4 and 5. While the two seemed like the perfect couple, they broke up when they realized they were on different pages. He told Bravo, “I talk to [Chelsea] all the time, great friends and the one thing that she said was, ‘You know, we’re at different aspects of our life,'” he explained in 2024.
• Although Austen didn’t date Shep’s ex-girlfriend, Taylor Ann Green, they did admit to kissing and having feelings for each other. However, because of her ties to Shep, the two remained friends.
• Olivia Flowers joined the show in Season 8 as Austen’s love interest. They dated for a few months before a very dramatic breakup because Austen refused to commit.

Venita Aspen

Venita has been a breath of fresh air since joining Southern Charm but she hasn’t dated many of the cast members or men connected to the series. In Season 10, she and Jarrett “JT” Thomas crushed on each other and dated for a short time before he ghosted her for another woman.

Taylor Ann Green

Taylor Ann Green joined the series as Shep Rose’s girlfriend. She didn’t become friends with the cast until she became serious with Shep. When Shep and Taylor eventually broke up, she was linked to Austen — even sending inappropriate photos to cast mate Whitney Sudler-Smith.

Taylor eventually moved on with Gaston Rojas, despite Southern Charm’s JT declaring his love for her.

Molly O’Connell And Salley Carson

Molly O’Connell and Salley Carson are new to the cast in Season 10 and their relationship backgrounds are still being explored.

In Season 10, Molly admitted that she’s had on-again/off-again flings with Whitney Sudler-Smith over the years, and that she found Shep Rose attractive.

Meanwhile, Salley admitted that she had slept with Shep in the past and used to date Taylor Ann Green’s current boyfriend, Gaston.

Let’s Not Forget Former Castmate Relationships

Southern Charm has had a long cast over the years outside of the core friend group. While some still pop up in the series from time to time, others are no longer affiliated with Bravo.

Tarnished former South Carolina treasurer, Thomas Ravenel, was a fascinating cast member as one of the older ones in the group. At the start of Season 1, he was on the prowl for a wife and mother of his future children. This wound up being fellow cast member Kathryn Dennis. When the pair broke things off, he moved on to Landon Clements, but it didn’t last.

When Olivia Flowers was in a fluctuating relationship with Austen Kroll, she also went on dates with Rod Razavi before saying they were better off as friends.

Likewise, former cast member John Pringle seemingly went after Madison LeCroy when she and Austen broke up. Similarly, he and Kathryn Dennis also shared kisses.