The Charleston School of Law alum is an OG star of the Bravo reality show, making his TV debut during season 1 in 2014. Olindo, for her part, joined the series as Conover’s girlfriend during season 3, which aired in spring 2016.
Despite moving in together during season 4, the duo called it quits in the fall of 2017 after less than three years of dating — but that wasn’t the last viewers saw of the former Charleston power couple.
“I think it was just a culmination of things that at the end of it, we were just two very different people that couldn’t get along,” Olindo told Bravo’s Daily Dish in April 2018 of the split. “It was sad because we did care about each other. You saw, we just could not get along.”
The L’Abeye founder explained that she was only 22 years old when she started seeing Conover.
“When I was younger, you just start dating someone because you have a couple things in common, and you’re attracted to each other and you have fun together,” she said at the time.
The entrepreneur noted that fans ridiculed her for allegedly not championing the Sewing Down South founder when he first took up sewing — but Olindo believed Conover was using crafting as a distraction from pursuing law.
“People think, ‘Oh, why can’t you support his sewing?’ It had nothing to do with me not wanting a boyfriend who sews. I don’t care at all about that. Hobbies are important, and I thought it was great,” Olindo added. “The reason I had a problem with it was Craig is a procrastinator, and he was using sewing as a way to procrastinate doing things that he actually needed to do, you know, important things. … Instead of doing something that he had a deadline on or whatever, he’d just sit and sew all night, not the actual fact that he sewed.”
Conover, for his part, called his split from Olindo “disappointing and sad” during a March 2018 Daily
“Naomie and I, we had the best of intentions. We were trying to work it out, but after a while we had to accept reality, and I wished things were different. I think we both did,” he explained at the time. “But instead of banging your head against the wall every day, you really have to look in the mirror and be like, ‘How long are we gonna keep lying to ourselves?’
Drama between the exes continued to be a major story line during season 6 of the series, especially after Olindo’s relationship with Shah became more public. "I just hope she’s not willing to sacrifice her own happiness trying to prove being right about us,” Conover said of his former girlfriend during the season 6 premiere. (Olindo
Olindo commented on Conover’s remarks during an interview with Entertainment Tonight, explaining, "There was a time when I was happy [with Craig].
After breaking up with girlfriend Natalie Hegnauer, Conover began casually dating Paige DeSorbo. The couple confirmed their relationship while attending Summer House’s Amanda Batula and Kyle Cooke’s September 2021 nuptials.
Following her split from Shah, Olindo rejoined the cast of Southern Charm for season 8. When asked about where she stood with Conover at the time, she played coy. “I mean, I don’t know how to answer this. You’ll just have to watch the show, I guess,” Olindo teased during an appearance on the “Skinny Confidential Him & Her” podcast. “I aired it all out on there.”
The France native acknowledged that fans wanted her to get back with Conover but insisted that she’s “definitely not” going to date him again. “He’s dating someone who I really like. Paige is great,” she added.