Relationship Timeline: A Look at Their Journey – Hollywood Life
- Craig Conover stars on Southern Charm.
- Paige DeSorbo stars on Summer House.
- Craig and Paige began dating in 2021.
Craig Conover and Paige DeSorbo discovered their romantic connection within the vibrant world of Bravo reality television. Although they were featured on separate shows for several years—Southern Charm for Craig and Summer House for Paige—they found themselves drawn together during the first season of Winter House in 2021. At that time, Craig, who was 34, was in a relationship with another person, yet Paige, aged 30, exuded an irresistible charm that caught his attention. By the fall of 2021, the couple officially went public with their blossoming relationship, much to the delight of their fans.
Fans of Bravo have become deeply invested in the journey of Craig and Paige’s relationship. Their romantic highs and lows unfolded on both Southern Charm and Summer House, captivating audiences with their dynamic interactions. Many speculated that the couple was on the brink of engagement; however, they have since parted ways. For those eager to learn more about the intricacies of Craig and Paige’s relationship, a comprehensive timeline detailing their journey is provided below!
How Craig and Paige’s Relationship Began
Craig and Paige first crossed paths in 2018, a time when Paige was in a relationship with Perry Rahbar. Reflecting on their initial meeting, Paige shared, “I met Craig, actually, three years ago and he was single. I had a boyfriend and I absolutely respected that I was in a relationship,” during an interview with US Weekly in October 2021. This respectful distance laid the groundwork for what would later become a significant connection.
Behind the Scenes of Filming Winter House
Craig and Paige became co-stars on the inaugural season of Bravo’s Winter House in early 2021. At that point, Craig was still involved with Natalie Hegnauer, who was not part of the show. Meanwhile, Paige found herself flirting with Andrea Denver during filming, but her heart remained captivated by Craig. The chemistry between them was undeniable, even amidst their complicated situations.
Paige recounted, “When we got to Vermont, I didn’t know he had a girlfriend. So, I was a little bummed when I first got there. But, of course, he was absolutely respectful to his girlfriend,” she disclosed to US Weekly. She expressed her gratitude for the situation, stating, “I’m so happy now looking back that he had a girlfriend because we built just a very platonic friendship, which is like the base of our relationship now. Everything really does happen for a reason.”
The Evolution of Craig and Paige’s Romance
Following the conclusion of filming Winter House, Craig ended his relationship with Natalie and actively pursued Paige. They sparked dating rumors when Paige made a trip to Charleston to visit Craig in April 2021, although she was quick to deny any romantic involvement. “Craig and I are a thousand percent not dating,” she insisted during an appearance on the Not Skinny But Not Fat podcast. “Craig and I have known each other for years. We’ve always gotten along. We’ve always been friends. We have, like, very similar personalities. We are not romantically involved or anything, but we are very good friends.”
However, the dynamics shifted as summer rolled in, and Craig began filming season 6 of Summer House. Their relationship took a romantic turn that September when they both attended the wedding of Amanda Batula and Kyle Cooke, sharing a cozy moment captured in a photo booth that Paige later posted on her Instagram Story.
Craig and Paige Officially Confirm Their Relationship
The couple confirmed their romance in a heartfelt interview with PEOPLE in October 2021. “It was done in a healthy way. We built a friendship and got to know each other first, and it all happened naturally,” Craig explained. “You see the foundation of our relationship start to form on the show.” He added, “We are pretty happy now. I don’t think either of us has ever dated someone else in the industry. We get each other; it’s nice. We really are each other’s biggest fans, which is something that I’ve always looked for.”
Going Public: Craig and Paige’s Instagram Debut
Craig and Paige officially declared their relationship on social media during the Southern Charm season 8 wrap party in December 2021. Paige shared a touching photo of Craig kissing her on the head at the celebration, captioning it, “Sew in love,” a reference to her boyfriend’s successful sewing business, Sewing Down South.
Craig’s Memorable Appearance on Summer House
Craig and Paige’s relationship was showcased on television for the first time during Summer House season 6, which aired in the winter and spring of 2022. The season captured their journey as they navigated the early stages of their romance, dealing with challenges such as Paige’s flirtation with Andrea and Craig’s rumored involvement with Kristin Cavallari. Paige shared with Entertainment Tonight that she began to realize how deeply she cared for Craig during this time.
“I can’t pinpoint a certain thing that he did or said; it was kind of just realizing how I felt about myself when I was with him,” she expressed in a January 2022 interview. “And it was just kind of undeniable. Little things that I would get excited about—if I had a text message from him on my phone—it didn’t even compare to when other guys would text me. So I knew that I was very into him a lot more than any other suitors that were around.”
Craig and Paige have maintained their visibility on each other’s shows, continuing to engage their audience. They also appeared together in season 2 of Winter House. Looking ahead, Paige is set to join season 9 of Southern Charm, which is scheduled to premiere in September 2023, ensuring their dynamic continues to be a topic of conversation among fans.
Future Aspirations: Craig and Paige’s Relationship Goals
Craig and Paige have been candid about their aspirations for their relationship, sharing insights with their fans. In May 2022, Craig disclosed on the Behind the Velvet Rope with Davi Yontef podcast that he had no immediate plans to propose to Paige on camera. He stated, “The answer would be ‘No’ from Paige. We do a good job of keeping some of our milestones outside of the camera’s reach. You won’t see a proposal until we’re at least together for a year.”
Just five months later, during BravoCon 2022, Paige expressed that she was not ready for an engagement with Craig at that moment. “I am not in a rush to do anything. I feel like I really love where we are right now,” she remarked. In an April 2023 episode of Summer House, Paige candidly admitted that the thought of getting engaged and married was “f scary” for her, which led to a temporary conflict between her and Craig, but they managed to resolve it.
The End of an Era: Craig and Paige’s Breakup
In December 2024, Paige opened up on the “Giggly Squad” podcast about her breakup with Craig. She expressed deep admiration, saying, “I have so much love and respect for Craig. I think he is one of the best people I have ever met in my entire life. I will remain the biggest fan of him and want the best for him, and he truly will get the best because he is the best. But with that said, I think it was just the right decision for both of us moving forward in our lives and the direction in our lives that we didn’t force.”