Southern Charm's Craig Conover's Love Life Has Left Fans Guessing

Since Southern Charm premiered in 2014, the Bravo reality show has provided fans with hours of entertainment. The reason for that is the fact that Southern Charm has starred several people fans care about, including Jarrett "JT" Thomas, who left the show after viewers learned about his health issues. Southern Charm fans have also cared about things like new cast members joining the show, Michael Kelcourse's passing, and Olivia Flowers' firing.

Arguably the Southern Charm cast member that fans are most invested in is Craig Conover. After all, fans want to know about Craig's business, and they are even more invested in his love life, which can be very dramatic, to say the least.

Southern Charm Fans Have Been Captivated By Craig Conover And Paige DeSorbo's Relationship

Since 2019, Paige DeSorbo has become one of Bravo's most notable reality show stars. After all, Paige has starred in episodes of Winter House, Summer House, and Southern Charm.

Before Paige rose to prominence, Craig Conover had already spent several years starring in a different reality show called Southern Charm. One of Southern Charm's only stars who has been at the heart of every season, millions of fans have followed the ups and downs of Craig's life.

Even after years of Craig being a reality star, it still seemed unexpected when he starred in seasons of Winter House and Summer House. As a result of Craig branching out his reality TV resume, he and Paige met and that changed both of their lives.

In November 2023, People published a timeline of Craig Conover and Paige DeSorbo's relationship. That article revealed that after Paige and Craig met during Summer House's fourth season, they began by building a friendship.

After their first meeting in Summer 2019, they began attending events together. In fact, Craig and Paige attended a wedding together before they made their relationship official in 2021.

After they made their relationship Instagram official in December 2021, Craig discussed his future with Paige in March 2022. During a Page Six interview, Craig revealed that he and Paige had been having some very big conversations.

During Craig Conover's March 2024 Page Six interview, he admitted that he and Paige were both aware at the time that their relationship might not last forever. “We’re both realists and obviously no one ever plans on breaking up… we hope that doesn’t happen, obviously.”

According to Craig, he and Paige were considering things like getting married and having children.

“We have talked about marriage and spending our lives together, which we’re happy about. We talk about kids and a family.”

After talking about potentially getting married some day, Craig and Paige have stayed together ever since.

While talking to People in November 2023, Craig Conover revealed he and Paige DeSorbo weren't rushing to engagement. “I love what we have now.”

However, as another article from TheThings detailed, Craig stated during a Summer House episode that it was "very probable" that he and Paige would break up.

"I mean, there's always that chance, right? We do live in different places. She lives in New York City, she loves New York. I love Charleston, I run a company out of Charleston. It's very probable. You'd be naive to be like, 'It's all just gonna work out.'"

In March 2024, EOnline reported about Paige's responding to Craig's comment during an episode of the "Giggly Squad" podcast. Instead of getting upset, Paige agreed with Craig's comment. "Honestly, I wasn't upset about it at all because I think everything he said I agreed with... Yes, in statistics people could potentially break up. We have a higher rate because we do long distance, but I think if we weren't acknowledging that we would be really naive."

Based on those remarks and the fact that Craig and Paige haven't gotten engaged after several years together, many observers expect their relationship may end soon. However, both of those comments in context show they may have just been trying to be realistic.

The Truth About Craig Conover's Complicated Past With Kristin Cavallari

After Craig Conover and Paige DeSorbo began dating, he was still involved with headlines about his history with the reality star legend Kristin Cavallari. Funnily enough, it seemed like Craig liked being a part of that drama as he said the most salacious thing about himself and Kristin.

During an episode of Summer House, Craig told Paige that he and Kristin had an intimate encounter. “No, I’ll tell you. I’ve hooked up with her before.”

In July 2021, there were rumors that Craig Conover, Kristin Cavallari, and Austen Kroll were in a love triangle. During the same Summer House episode when he said he hooked up with Kristin, Craig stated that Austen was upset about that. “[Austen] hates that I was making out [with Kristin].”

However, Kristin has denied ever hooking up with Craig or his co-star Austen.

While Kristin denies being intimate with Craig, that doesn't mean that she says that things never got physical at all between them. Instead, a September 2023 US Weekly article revealed that Kristin admitted she might have kissed Craig during an appearance on Watch What Happens Live With Andy Cohen.

“I may have been drunk one night and kissed Craig.”

During the same talk show appearance, Kristin stated that she and Craig were only friends, however.

Craig Conover's Relationships From The Past

Since Craig Conover has been in public for many years now, fans have gotten to see him get involved with several other women in the past.

In January 2024, Us Weekly published an article about which Southern Charm stars have dated each other. That article in part focused on Craig's most notable relationship from the past.

That article revealed that Craig was involved with Kathryn Dennis during Southern Charm's first season. However, Us Weekly's article revealed that Craig's relationship with Naomie Olindo lasted a lot longer.

During the third, fourth, and fifth seasons of Southern Charm, fans saw Craig and Naomie date for three years. After being at the center of the show for those three seasons, Craig and Naomie broke up.

However, Craig and Naomie later confirmed that they hooked up in 2021 while in Las Vegas.