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. As the two began growing up, they no longer saw eye to eye on what they wanted out of the relationship.
“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. “You don’t think about the attributes that would make you get along with someone, their work ethic, and all the different adult things that matter that don’t matter when you’re a 22-year-old kid.”
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 Dish interview.
“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?’ So fortunately, no one did anything bad. No one stepped out or cheated or anything, so there wasn’t really any anger.”
Viewers witnessed the exes sparring on many occasions throughout season 5 after they first parted ways, but the “Pillows and Beer” podcast cohost hoped to mend fences down the line. “There’s no reason we shouldn’t be friends,” he added. “I still love the girl to death. She’s great.”
The duo’s ups and downs continued on season 6 of Southern Charm, but outside of the show, they were able to make their way back to being friends in time. Both Conover and Olindo are set to reunite on screen for season 8 of the series, which will premiere in 2022.
Scroll down to relive the reality stars’ relationship from its start: