Craig Conover is basically the resident "hopeless romantic" of Charleston. If you’ve watched even one episode of Southern Charm, you know the drill. He falls hard, he sews some pillows, and then things usually go south in a way that fuels about three seasons of reunion drama. Honestly, his love life has been a rollercoaster that Bravo fans can't stop riding.
From the college sweetheart days to the high-profile breakup that rocked the "Bravoverse" in early 2025, the Craig Conover dating history is a literal timeline of reality TV evolution. He went from a law student who couldn't finish his bar prep to a successful entrepreneur, but his choice in partners has always been the real headline.
It’s messy. It’s sweet. Sometimes, it’s just plain confusing.
The Naomie Olindo Era: First Love and Growing Pains
Before the pillows, there was Naomie. They actually met way back at the College of Charleston. Craig was a senior, she was a freshman, and the timing was just off. But like a classic rom-com, they found their way back to each other in 2015.
For three years, they were the couple. They lived together. They traveled. They seemed like they were going to be the first Southern Charm duo to actually make it to the altar. But cracks started showing. Naomie was driven, structured, and—let’s be real—a little bit hard on Craig’s "hobbies." Remember when she mocked him for wanting to sew? That didn't age well, considering his multi-million dollar business now.
They officially split in September 2017. It was brutal.
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What most people forget is that they actually had a "closure" hookup in Las Vegas years later, right after Naomie broke up with Metul Shah in 2021. It wasn't about getting back together; it was about finally putting that chapter to bed. Craig has since called her his "first love," and honestly, you can still see the mutual respect there.
The Natalie Hegnauer "Crosstown" Connection
Then came Natalie. They met in Aspen in January 2020, right as the world was about to shut down. Because of the pandemic, their relationship moved at warp speed. She moved into his Charleston house, and suddenly they were a "quarantine couple."
She was a bit of a mystery to fans. She appeared on Season 7 of Southern Charm, but she never seemed fully comfortable in the spotlight. Rumors swirled that she was just looking for a TV spot, but Craig defended her tooth and nail.
They lasted about a year, officially ending things in May 2021. The weirdest part? Natalie actually had a past connection to Austen Kroll (because the Charleston dating pool is essentially a bathtub). Once they split, the door swung wide open for the most famous relationship in Craig's history.
Why the Craig Conover and Paige DeSorbo Split Still Matters
If you’re a Bravo fan, December 2024 was a dark month. After three years of being the king and queen of crossover reality TV, Paige DeSorbo announced on her Giggly Squad podcast that she and Craig were over.
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It felt like a gut punch. They were the couple that proved Summer House and Southern Charm could coexist. They started as "non-exclusive" buddies in 2021, navigating a long-distance relationship between NYC and Charleston. We watched them argue about moving, getting engaged, and whether or not Paige would ever leave her beloved Manhattan.
The Breakdown of the Breakup
- The "Cat" Theory: In a 2025 episode of Southern Charm, Craig pointed out a bizarre pattern. Apparently, his last three girlfriends (Naomie, Natalie, and Paige) all got a cat right before dumping him. He calls it "the kiss of death."
- The AI Controversy: This is where it gets weird. In early 2026, it came out that Craig actually used ChatGPT to process his feelings after Paige left him. He even admitted to crying while "talking" to the AI. Jenny McCarthy famously called this a "red flag" on Watch What Happens Live, but hey, everyone grieves differently.
- The "Mutual" Lie: Paige claimed the split was mutual and healthy. Craig later went on TV and said he was basically blindsided. He was planning to move to New York for her. She was ready to be single.
They weren't on the same page. Simple as that.
Who is Craig Conover dating now?
As of early 2026, Craig isn't crying over chatbots anymore. He confirmed in March 2025 that he is "seeing someone" and is officially out of his single era.
He’s kept her identity mostly under wraps, which is a massive change for him. No more filming every date. No more Instagram-official posts within the first week. He did mention that he prefers meeting people "organically" now rather than using apps.
There were rumors about him dating his co-star Salley Carson, but he shut those down pretty quickly. Whoever the new woman is, she’s entering a version of Craig that is much more settled—and probably a lot more cautious about who he brings into his "sewing" empire.
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Lessons from the Craig Conover Playbook
If you’re looking at this history for dating advice, here’s the reality. Craig is the king of the "slow burn" that turns into an "all-in" fire. He stays friends with his exes (mostly), but he also tends to ignore red flags if he’s "sew in love."
Actionable Insight for Fans: If you're following Craig's journey, the biggest takeaway isn't about the drama. It's about his evolution from someone who felt "less than" in a relationship (the Naomie years) to someone who knows his worth and his business. If you're going through a breakup, maybe skip the ChatGPT therapy and just focus on your own version of "sewing pillows."
The most important thing to watch for in the upcoming season of Southern Charm is whether he finally breaks the "long-distance" habit. He seems to thrive when he has his own space, but his history shows he’s always looking for someone to share the porch with. For now, the "dating history" book is still being written, one Charleston sunset at a time.
To stay updated on Craig's current relationship status, keep an eye on his Pillows and Beer podcast updates, as he often drops breadcrumbs there before they hit the tabloids.