‘Southern Charm’ Cast’s Dating History: Inside Shep Rose, Kathryn Dennis, Craig Conover, Madison LeCroy and More Stars’ Love Lives

When it comes to Southern hospitality, the cast of Southern Charm doesn’t stop at being “just friends.” In fact, some of the show’s biggest names, including Shep Rose, Kathryn Dennis and Austen Kroll have a history of dating their costars — in between off-camera romances.

Kathryn, who shares two children with former Bravo personality Thomas Ravenel, was a bit of a wild child when the show first premiered in February 2014. During season 1, she hooked up with costar Whitney Sudler-Smith before romancing Thomas. She also flirted with Craig Conover and got cozy with Shep.

“Without revealing too much, I had a wonderful time with Kathryn during our brief affair. I remember reading my favorite passages of books to her out loud on my couch, and I remember her writing me a four-page note and leaving it on my coffee table one morning,” Shep wrote in his 2021 memoir, Average Expectations, noting he hooked up with Kathryn before she was a full-time cast member. “The note was so nice and raw and real that it still makes me feel warm and fuzzy to this day. I also remember tearing each other’s clothes off … Oh wait, I said I won’t reveal too much. She was lovely and I do believe I had a calming influence on her and maybe still do.”

Although Kathryn and Shep’s romantic relationship included more than one sexual encounter, the model revealed in May 2019 that she doesn’t regret that they were never official. “I will say life would be a lot different if I would have pursued him,” she told a caller on Watch What Happens Live With Andy Cohen at the time. “But I don’t really think I have a one that got away. I think I have a one that won’t go away.”

Fans have watched a lot of relationships crash and burn throughout Southern Charm’s seven seasons, including Austen’s romance with Chelsea Meissner and Madison LeCroy. Craig’s ups and downs with ex-girlfriend Naomie Olindo were also a big topic of conversation through the years.

While some stars, including Cameran Eubanks and Leva Bonaparte, got married before appearing on the reality show, others have gone on to have successful romances outside of the show.

Several cast members, including Landon Clements, Danni Baird and season 7 newcomer John Pringle, have embraced the single life aspect while hanging out in Charleston, South Carolina.

Scroll down for a complete guide to the cast of Southern Charm’s relationships:

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Kathryn Dennis

The model hooked up with costar Whitney ahead of her romance with Thomas in season 1 of the series. Kathryn dated Thomas on and off until 2016. They share two children, daughter Kensie and son Saint.

Kathryn revealed in 2018 that she and costar Shep have hooked up multiple times before and after she became a mother. The two have remained friends over the years but never had a serious relationship. It was revealed during season 6 of the Bravo show, which aired in 2019, that Kathryn again hooked up with Whitney, although he denied that the incident ever happened for multiple episodes.

The Charleston native briefly dated former Florida politician Joseph Abruzzo in 2018 before getting into a relationship with country singer Hunter Price. Kathryn met the singer during a New Year’s Eve trip to Nashville in 2018, but the two split after less than one year together in August 2019.

The TV personality was first linked to Chleb Ravenell in July 2020 after the pair were seen celebrating his birthday. Us exclusively confirmed in November 2021 that the couple split and were no longer living together after more than one year of dating.

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Shep Rose

Shep has a reputation for being one of the cast’s biggest flirts and a total ladies’ man. Ahead of the show, he dated Danni, whom he’s remained close friends with for years. He has had flirtations with former costars Landon and Chelsea, but nothing ever came from either romance.

The Average Expectations author most notably had an on-again, off-again hookup with Kathryn for years, but they never crossed over into something serious. He briefly dated the winner of his short-lived spinoff, RelationShep, Bella Clark in 2018.

Shep confirmed his relationship with Taylor Ann Green in May 2020 after sparking relationship speculation earlier that year. Taylor made her Southern Charm debut in season 7, which premiered the same year. In January 2021, the TV personality admitted that he cheated on Taylor by kissing an ex but revealed during the season 7 reunion that they were still together. Us confirmed in July 2022 that the pair split.

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Craig Conover

Craig had a flirty relationship with Kathryn during season 1, but he was friend-zoned after she started seeing Thomas. He eventually began dating Naomie, whom he first met at the College of Charleston when he was a senior and she was a freshman. After the designer graduated from school, the pair reconnected and dated for three years before calling it quits in 2017.

The Sewing Down South founder confirmed his relationship with Natalie Hegnauer in December 2020, hours ahead of her Southern Charm debut. The pair met ahead of the coronavirus pandemic shutdowns in early 2020 and quarantined together in South Carolina. They called it quits the following year, with a source noting to Us in August 2021 that “they are still good friends, it just wasn’t a good match.”

Two months later, Us confirmed that Conover is dating Summer House star Paige DeSorbo after they filmed Winter House together earlier that year. “Their friendship turned into a relationship as they’ve spent more time together in recent weeks,” an insider detailed in October 2021.

Craig raised eyebrows in July 2021 when he and Austen were rumored to have been in a love triangle with Kristin Cavallari. The Laguna Beach alum denied at the time that she was anything more than friends with either Bravo star. Craig, however, claimed during a January 2022 episode of Summer House that he had been intimate with Cavallari after he was confronted by Paige in the Hamptons.

“No, I’ll tell you, it was, like, I’ve hooked up with her before,” the Delaware native said during the episode, which was filmed in July 2021, claiming that Austen “hates that I was making out [with Kristin].”

When the episode aired, a source exclusively told Us that Craig was “making it up — it’s not true,” adding, “They never hooked up.”

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Madison LeCroy

The stylist was married to Josh Hughes from 2010 to 2015. They share son Hudson, whom they welcomed in November 2012. When fans of the reality show met Madison, she was starting a romance with costar Austen. The pair’s on and off relationship last two years before Us exclusively confirmed in December 2020 that they had called it quits.

Ahead of her breakup with Austen, Madison had a flirty relationship with season 7 newbie Pringle. Their checky interactions played out on Southern Charm, but never became anything serious.

Us confirmed in January 2021 that the Greenville, South Carolina, native was “having fun” and getting to know former quarterback Jay Cutler following his split from Kristin Cavallari in April 2020. The relationship quickly soured after Madison made a video directed at the Uncommon James founder, with whom Cutler shares three children, because Cavallari was spotted hanging out with Madison’s ex-boyfriend Austen.

“The world is full of users. 10 years. Can’t break that,” Cutler and Cavallari posted on their Instagram accounts. The TV personality then clapped back at the post by releasing her alleged text messages with Cutler, ending the short romance.

The same month, Madison was accused of “flying around the country [and] sleeping with married men. Ex-MLB players,” by Craig during the season 7 Southern Charm reunion. The Southern Belle denied the allegations, but she later confirmed that the man in question was Alex Rodriguez, who was engaged to Jennifer Lopez at the time. “He’s never physically cheated on his fiancée with me. [It’s] never been physical,” she told the New York Post’s Page Six in February 2021. Two months later, Lopez and Rodriguez announced their split.

Madison moved on with a new mystery man in June 2021, later revealing that his name was Brett Randle. She hinted at the new romance in April of that year, telling a fan via Instagram that she had a boyfriend. She announced their engagement in October 2021 while still keeping his last name under wraps. They wed in November 2022.

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Austen Kroll

Austen briefly dated costar Chelsea during season 4 of Southern Charm in 2017 before things fizzled out. Their romance played out a little bit in season 5 when he was dating the stylist’s friend Victoria, who continually questioned his loyalty amid Austen’s friendship with Chelsea. The Kings Calling Brewing founder found love again with Madison, but the pair’s rocky relationship came to an end after two years, with Madison confirming to Us in December 2020 that they were over.

Following his split from Madison, Austen sparked romance speculation with Cavallari, after the pair partied together in late 2020. “She came to town with her friend Justin and the four of us [with Craig] had dinner,” Kroll told Us in November 2020 of their friendship. “We’ve all been in contact ever since. We’re in this, like, big old group chat, and the group chat is active. We had a blast with them.” The duo were again spotted with their mutual friends in June 2021 when the Laguna Beach alum came to South Carolina for a visit, but have denied dating rumors in the past.

Austen briefly romanced Winter House costar Ciara Miller in early 2021 while filming the spinoff series in Vermont. The duo were flirty during Austen’s visit to the Hamptons that summer, which played out on season 6 of Summer House. The North Carolina native, however, got himself into trouble when he made out with longtime friend Linsdsay Hubbard while staying at the group’s house.

In May 2022, Austen confirmed to Us that he was dating Olivia Flowers, who joined the cast of Southern Charm for season 8. “You will certainly see where it begins, then how it ends,” he teased at the time, noting the pair had been friends for a while before things turned romantic. “And it certainly is some ebb and flows as I’m trying to figure it out.”

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Whitney Sudler-Smith

The Southern Charm producer hooked up with Kathryn before she started seeing his BFF Thomas in season 1 of the reality series, which aired in 2014. It was later reported that the two were intimate again before the start of season 6 in 2019, which Whitney denied on more than one occasion.

Following his initial fling with Kathryn, Whitney began dating Austrian model Larissa Marlot. The pair first met at a New York City party in 2013. They dated on and off for six years with Larissa popping up here and there on the Bravo series before the two seemingly split in 2019. They were last photographed together in January of that year.

During a break from Larissa, Whitney dated a model named Daisy, who fans met in season 4. The two were linked in 2017 before he got back together with Larissa.

Naomie confirmed during season 8 of the series, which aired in the summer of 2022, that she and Whitney had hooked up after his mom’s dog’s wedding.

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John Pringle

The season 7 newcomer was briefly married to San Diego makeup artist Heidi before splitting and relocating to his home state of South Carolina. The former spouses share two sons, Quinn and Asher. During his first season on the show, which aired in 2020, he was caught up in a love triangle between costars Madison and Austen.

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Leva Bonaparte

The restauranter, who joined the cast in season 7, has been married to Lamar Bonaparte since April 2013. The couple share son Lamar Jr., whom she calls “Little.”

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Naomie Olindo

Olindo joined the cast of Southern Charm during season 3, which aired in 2016, after she began dating Craig. The pair’s ups and downs and eventual split — they called it quits in 2017 after nearly three years together — were a major story line on the show for three seasons.

The L’Abeye owner, who left the show in 2020, introduced boyfriend Metul Shah to her Instagram followers in April 2018. Three years later, the couple announced that they were moving to New York City in July 2021. News broke in mid-July 2021 that the pair had called it quits and Olindo was back in Charleston after a brief move to the Big Apple.

Naomie made headlines in the summer of 2022 when she confessed to hooking up with Craig in Las Vegas one year prior. The brief reconciliation played out on season 8 of the series. During an August 2022 episode, the France native also revealed that she and Whitney hooked up and he “stayed the night” after the group’s dog wedding.

Credit: Courtesy Danni Baird/Instagram

Danni Baird

Danni dated Shep before the two costarred on the reality series. The pair have remained friends and at times, Danni has tried to help her costar navigate his other romances. The artist got engaged to longtime boyfriend Todd Baldree in July 2016. However, weeks before they were set to tie the knot, she confirmed that they called off the engagement in August 2017.

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Cameran Eubanks

Cameran, who left the series after six seasons in May 2020, has been married to Jason Wimberly since April 2014. They share daughter Palmer. The real estate agent’s husband’s alleged cheating scandal, which made headlines in 2020, didn’t, however, play a part in her exit. The Real World alum explained at the time that she chose to leave the show “months ago” via her Instagram, adding that it had “absolutely nothing to do with ridiculous and fake rumors about my marriage.”

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Thomas Ravenel

The former politician, who was fired from Southern Charm after season 5 following several sexual assault allegations, first hooked up with Kathryn during season 1. The pair, who share daughter Kensie and son Saint, dated on and off until their 2016 split.

Thomas then dated Ashley Jacobs for more than one year before calling it quits in 2018. The former couple’s rocky relationship (and drama with Kathryn) played out on seasons 5 and 6 of the Bravo series. Following their breakup, Ashley moved back to California and got engaged to Mike Appel in August 2019. The pair announced in June 2021 that they are expecting their first child together after secretly tying the knot.

The Bravo personality, for his part, welcomed his third child, son Jonathan, in June 2020 with Heather Mascoe. Four months later, he revealed that he is “getting married,” but didn’t say to whom. In December 2020, the Daily Mail confirmed that Thomas is engaged to his girlfriend Heather.

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Chelsea Meissner

The hairstylist dated costar Austen on and off during seasons 4 and 5 of the Bravo show, which aired from 2017 to 2018. During their relationship, Shep hit on Chelsea, but the pair never became anything more than friends.

The Hilton Head Island, South Carolina, native, who left the series in 2020 ahead of season 7, went public with sailor Nick Dana in 2018. She later spoke about the long-distance romance during season 6 of the series but hasn’t posted any photos of him since their trip to El Salvador in January 2020.

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Landon Clements

Landon was married to British businessman James Maby for five years before she joined the cast in 2015. The interior designer left the show in 2017 after season 4 and moved to California to start a career in residential real estate. While on the series, rumors surfaced that Landon and Thomas had sparked a romantic relationship, but she claimed they were just friends after knowing him for years.

She also had a playful relationship with Shep, who she has known since college, telling him during season 3 that she was “in love” with him.