Sew what! Craig Conover and Naomie Olindo caught fans’ attention from the moment they first appeared as an item on Southern Charm — and their 2017 split kept them in the spotlight.
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:
The twosome initially met while attending the College of Charleston. Courtesy Naomie Olindo/Instagram
The duo reconnected after college and began dating. Courtesy Naomi Olindo/Instagram
Olindo first appeared on season 3 of Southern Charm, which was filmed in 2015 and aired the following year. Meanwhile, Conover has been part of the cast since day one. Courtesy Naomie Olindo/Instagram
The couple celebrated pal Shep Rose’s birthday with a ‘70s-themed bash. Courtesy Craig Conover/Instagram
“Tuk-tuks and jet packs on the other side of the world,” Conover captioned a snap with his then-girlfriend in Thailand. Courtesy Craig Conover/Instagram
The pair jetted off to Paris to kick off the new year. Courtesy Craig Conover/Instagram
Olindo and Conover moved in together, which was later shown on season 4 of the Bravo series. Courtesy Naomie Olindo/Instagram
After shopping for a promise ring on season 3 of the reality series, the Delaware native revealed to Andy Cohen that he did have plans to get down on one knee. "When I learn to ask her dad in French," Conover said during an appearance on Watch What Happens Live about his proposal timeline. "Which will probably take another year." Courtesy Naomie Olindo/Instagram
The then-couple dressed up as the Joker and Harley Quinn for Halloween. Courtesy Craig Conover/Instagram
“We did it folks! I still can't really walk just yet but it was more satisfying than I could've ever imagined. A lifetime of foot & ankle injuries caught up to me around mile 20, but thanks to @naomie_olindo we finished the @nycmarathon hand-in-hand,” Conover wrote via Instagram after running the New York City Marathon with Olindo. “It was well worth the pain as we have raised almost $10,000 towards our cause so far!” Courtesy Craig Conover/Instagram
The Charleston residents enjoyed a weekend away for costar Cameran Eubanks' birthday. Courtesy Craig Conover/Instagram
“HAPPY BIRTHDAY to my greatest adventure! I'm only mean to you because I love you. I'm so proud of your accomplishments this year,” Olindo gushed via Instagram. “You ran a marathon, bought a house, filmed another season, went on a mission trip, raised thousands for charity, grew a garden, took up (many) hobbies, are taking the BAR and traveled the world. I love you with all my heart! #youngcraig.” Courtesy Naomie Olindo/Instagram
Conover surprised Olindo with a getaway after she finished finals for graduate school. Courtesy Craig Conover/Instagram
“My 🍯forever,” the businesswoman called Conover while attending a friend’s wedding. Courtesy Naomie Olindo/Instagram
The pair broke up after more than two years of dating. The fallout of their split was caught on camera during season 5, which aired in spring 2018. Courtesy Naomie Olindo/Instagram
Olindo told the Daily Dish that her “biggest regret” toward the end of her relationship with Conover was how mean she was to him. “It's funny because now I'm in such a different headspace than I was eight or nine months ago, and so [I'm] watching back how angry I was all the time, and I'm like, 'Why did you let this drag out so long? Why didn't you just get over it and act like a nice human being?'" she told the outlet. "It's very weird just to watch back, just the anger, really. I wish I had been nicer to him because Craig is such a nice person. He's like a puppy. I wish I hadn't been such a bitch, but oh well. It is what it is now." Courtesy Naomie Olindo/Instagram
Olindo moved on with Metul Shah. The physician made his Southern Charm debut one year later. Courtesy Metul Shah/Instagram
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 exited the reality show in 2020 following the season 6 finale.) Olindo commented on Conover’s remarks during an interview with Entertainment Tonight, explaining, "There was a time when I was happy [with Craig]. That time is over and I’m with somebody that makes me feel very balanced and just very good and, you know, everything just feels kind of right right now, and I think it might have been hard for Craig to see that, and I tried not to rub it in his face or anything like that." Courtesy Metul Shah/Instagram
News broke that Olindo and Shah called it quits after three years. The Blueprint to Breakup cocreator later claimed she discovered that the doctor was having an affair with his ex-girlfriend, which led her to end the relationship. “It was, like, a year's worth of texts with his ex and explicit pictures and, you know, the whole nine yards. So I read through them for a little bit,” Olindo recalled during a February 2022 episode of the “Skinny Confidential Him & Her” podcast, describing the moment learned that Shah had cheated by looking at his computer. "I called him, and I was like, 'Hey, I just want you to know, I saw the messages with Sophie and this is done.' And [I] hung up the phone, and he tried to call me, you know, a hundred times.” Courtesy Naomie Olindo/Instagram; Courtesy Metul Shah/Instagram
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. Jonathan Leibson/Polk Imaging/Shutterstock
“She’s been really happy. I think she’s relieved in a weird way,” Conover said about his ex-girlfriend on Watch What Happens Live With Andy Cohen after a fan asked how Olindo was coping with her breakup from Shah. “And she’s happy to be back in Charleston and things happen for a reason. I don’t think she was that happy in her relationship. But I think she’s just happy to be living her own life again.” MJ Photos/Shutterstock
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. Tommy Garcia/Bravo
The reality star detailed his breakup from Olindo in his memoir, Pillow Talk: What’s Wrong With My Sewing? “Despite what viewers saw on the show, Naomie in private really didn’t have a problem with my lack of a viable profession. She knew I was trying to finish my thesis so that I could then take the bar, and it didn’t bother her,” Conover wrote. “What bothered her was my schedule; what bothered her was how I went about doing what I did. … It was as if once the camera turned on, Naomie became the girlfriend she thought the audience wanted to see.” He exclusively told Us the same month that he interviewed his ex-girlfriend for the book, noting, “She had a lot of input and was very much involved.” Although Conover said he didn’t think Olindo had read the memoir at that point, he told Us that they were in a good place following her split from Shah. “She texted me some really nice messages and we had some nice talks, and I was a proponent of her coming back [to Southern Charm]. I think she enjoyed coming back,” the author said. “I think the viewers will like to see her and it should be a positive journey for most people. … You’ll get to see a lot of it on Southern Charm, but it was conversations that were long overdue, and I wish her the best. There’s no negativity there.” Stewart Cook/Shutterstock; Courtesy Naomie Olindo/Instagram
During an appearance on Watch What Happens Live With Andy Cohen, DeSorbo seemingly confirmed that Olindo and Conover hooked up during the early days of her romance with the Pillow Talk author. “OK, I’m going to be totally honest. I feel like if you’re gonna hook up with your ex-girlfriend, you should do it in Vegas,” DeSorbo said. “And so, when I heard those rumors, I wasn’t that mad. Just because I was in New York, doing whatever I wanted and he didn’t hear about my rumors. So I was like, ‘OK, let’s keep this on the forefront.’” Later that month, the season 8 Southern Charm trailer confirmed the hookup as well as Conover told Olindo why their dynamic felt “awkward” at times. “We’re not just exes, we hooked up recently,” he said. Bravo
Olindo exclusively told Us what led to her and Conover’s Las Vegas fling, noting that things are “good” between her and the author’s new girlfriend, DeSorbo. “I was surprised at how much emphasis was put on it in the episode because I think other people made it a much bigger deal than it was to me and Craig,” Olindo said of the hookup that took place after her split from Shah in summer 2021. “It was sort of like a time and place thing where it’s like, ‘OK, I know you, I trust you, we were both like fresh off breakups.’ This is a really long time ago now, but it was never like, ‘Oh, we need to get back together, blah, blah.’ It was just like a comfort thing — a very temporary comfort thing.” Stephanie Diani/Bravo
Conover, for his part, exclusively told Us he’s OK with how everything went down between him and Olindo. “I've said it's [the] closure that I didn't realize that I needed,” he explained of the Las Vegas affair. “As tough as this is to say about some things, I'm happy that it happened. It was just closure that I was able to be, like, ‘You know what? I can finally see what I want for my future and life.’” He added: “We had a long history together, you know, we knew just because we hadn't talked in four years, we still dated for three. So, I think she had gotten her world turned upside down — finding out [Metul] was cheating on her was terrible. I think temporary comfort's a good word for it. It was good for her and it was the closure I needed.” Stephanie Diani/Bravo
“The delivery was harsh, but he was like, ‘It helped motivate me,’” Olindo exclusively told Us while reflecting on how she treated Conover and is passion for sewing during season 5, shortly after they split. “Not that exact conversation but some of the conversations we had, he’s like, ‘It kind of helped motivate me sometimes.’” She added: “If it helped him even one percent — even though I hate that I was mean — then, yeah, I don’t regret it.” Olindo also noted that she is happy with where she and Conover are now after all of their ups and downs. “[We’re] definitely better as friends. We learned so much from each other and from the whole situation that there’s no way either one of could regret that,” the businesswoman told Us. “It is what shaped us to go and have a healthy relationship. No regrets there.” Stephanie Diani/Bravo; Charles Sykes/Bravo
During season 8, episode 7 of Southern Charm, Conover told Olindo that they needed to stop hanging out one on one amid his relationship with DeSorbo. “Unfortunately, there are still boundaries at the end of the day that have to be there,” he explained during a coffee date, which was filmed in late 2021. “I like that we can be friends. My path is taking me [toward] a relationship with Paige. At the end of the day, you are my ex-girlfriend and it’s just not appropriate to hang just yet.” The Delaware native later revealed during a confessional that DeSorbo was uncomfortable with him spending time with Olindo outside of group settings after Conover and Olindo hooked up in summer of 2021. “I think that Paige is being very understanding even though she doesn’t understand it because she lives in New York where you don’t run into your exes,” the OG Southern Charm star said in a confessional. “She has been patient with me hooking up with Naomie while me and Paige were figuring stuff out. I don’t want to push it by disrespecting her any further.” Naomie, for her part, was shocked by Craig’s comments but didn’t argue. “If I thought that we weren’t on the same page I wouldn’t have asked Craig to get coffee. I’m not a weirdo,” she told the cameras after the meeting. “I’m not trying to get with Craig if he has a girlfriend. That’s just not how I am. If Craig and Paige feel awkward that’s on them, not me.” Courtesy of Naomie Olindo/Instagram
Conover reached his breaking point with Olindo during Southern Charm season 8, episode 8, which aired on August 11. After the businesswoman seemingly overstepped when she insisted that Conover give his girlfriend, DeSorbo, his jacket at a dog wedding during the show, the exes had a heated conversation about where they stand. “What is going through Naomie’s head where she thinks she knows what’s best for me and my girlfriend?” the former law school student said during a confessional. “I don’t think she’s getting it. This is not respecting boundaries.” Following the union of Little Craig (Shep Rose’s dog) and Peaches (Patricia Altschul’s pup), Olindo confronted Conover about how “awkward” he had been toward her recently. “It’s a respect thing. … We’re not just exes, we hooked up recently,” Conover explained. Olindo, for her part, wondered whether him being “uncomfortable” around her was similar to how she used to feel around him when she was dating Shah. “Because when I was dating Metul and you and I were around each other, I thought that I was not allowed to interact,” she explained. Conover quickly shut her down, saying, “That’s because you were with someone who was controlling as f—k. You were never in my position. You left a loving relationship to be with a controlling a--hole who cheated on you.” Christopher Polk/Shutterstock
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