Craig Conover and Naomie Olindo's Relationship Timeline
Before they were reality TV stars on Bravo's Southern Charm, Craig Conover and Naomie Olindo were students at the College of Charleston, where the future couple first crossed paths.
Conover was about to graduate from the South Carolina school, while Olindo was just beginning her studies. Despite Conover's interest in Olindo, timing was not in their favor, though the Sowing Down South founder later admitted he still had Olindo on his mind even after graduation.
"I knew with Naomie that if there was ever any girl I was going to date, it was going to be her," Conover told Bravo's The Daily Dish of Olindo in 2016.
Matt Winkelmeyer/WireImage / Charles Sykes/Bravo/NBCU Photo Bank/NBCUniversal via Getty
Years after their first meeting, they became a couple and dated for nearly three years before splitting up in September 2017. Fans of the Bravo reality series saw Conover and Olindo move in together, travel the world and run a major marathon during the course of their relationship.
RELATED: Southern Charm: Naomie Olindo Returns for Season 8 as Ex Craig Conover Says They 'Hooked Up'
Now, with season 8 of Southern Charm teasing a new chapter in their story that includes a post-breakup hookup and a return to the series for Olindo (who bowed out of season 7), there's renewed interest in how Conover and Olindo's relationship initially unfolded.
From their international travels to their athletic pursuits, here's everything you need to know about Craig Conover and Naomie Olindo's relationship.
2009: Craig Conover and Naomie Olindo meet at the College of Charleston
Craig Conover Instagram
The two College of Charleston students met when Conover was a senior and Olindo was a freshman. Conover was interested right away, but Olindo didn't reciprocate his feelings.
"I remember the first time I saw her, she became everything in my head, but she wouldn't give me a chance," Conover said in a 2016 interview with Bravo's The Daily Dish. "[She] was the only girl I would put any effort into, like I would go out of my way to go over to her table or walk across the bar or whatever, the club, and try and talk to her. She would just look at me and look back at her phone and keep texting. I was like, 'Oh my God!' "
May 2015: Craig Conover and Naomie Olindo become Instagram official
Craig Conover Instagram
Conover and Olindo reconnected in 2014 after she texted him, and they started dating shortly after. In May 2015, Conover made their relationship Instagram official when he posted a black-and-white photo of him and Olindo together. For the caption, he simply tagged Olindo's Instagram handle.
May 2015: Craig Conover and Naomie Olindo travel to New York City
Olindo returned the favor that same month when she posted Conover on her own Instagram page for the first time. She shared a photo of the couple from their trip to New York City, where they attended a New York Rangers event at Bryant Park. Olindo added a cheeky caption to the photo, writing, "Google him lol (in full sarcasm voice)," as a nod to Conover's Southern Charm fame.
Late 2015: Craig Conover and Naomie Olindo move in together
Craig Conover Instagram
Viewers of Southern Charm learned that Conover and Olindo had moved in together during the season 3 premiere on April 4, 2016. The couple was living in a house owned by Olindo's parents, with the understanding that they would need to move out once the house was sold.
March 18, 2016: Craig Conover and Naomie Olindo attend Charleston Fashion Week
"So much fun watching all the cool shows at @chasfashweek with my bestie," Olindo captioned an Instagram post of her and Conover at Charleston Fashion Week in 2016. Olindo went on to thank two hairstylists for doing their hair for the occasion, including Madison LeCroy, who would later join the Southern Charm cast in season 6.
Conover told Bravo's The Daily Dish that one of his first dates with Olindo was at a previous Charleston Fashion Week. "We had a blast together, and she got to see that I'm actually a nice person and not a douchebag," he said. "She got to see the real person, and we kind of both knew that night that it was going to be a pretty long thing."
April 2016: Craig Conover surprises Naomie Olindo with a promise ring
In the second episode of Southern Charm season 3, viewers watched as Conover hid a promise ring in a jewelry box and then presented it to Olindo. Conover said he opted for a promise ring over an engagement ring because they had only been together for a year and wanted to take their time.
"I did want to give her something that symbolizes how I feel about her and that she can wear around with her," Conover said in an interview with Bravo's The Daily Dish. "I know that she wanted the same thing. It's kind of like a fun teaser."
June 2, 2016: Craig Conover and Naomie Olindo travel to Italy together
Naomie Olindo Instagram
"Eataly you did not disappoint," Olindo captioned a photo of herself and Conover during their trip to Italy in June 2016. The pair traveled to the village of Riomaggiore in Cinque Terre.
November 6, 2016: Craig Conover and Naomie Olindo run the New York City Marathon
After completing the 2016 New York City Marathon together, Conover celebrated the couple's achievement on Instagram with a selfie of the pair and their medals.
"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," he captioned the post.
In a since-deleted Instagram post, Olindo shared that they finished the race in six hours and 16 minutes. "It feels pretty awesome," she wrote.
March 8, 2017: Craig Conover surprises Naomie Olindo with a getaway
Craig Conover Instagram
Conover took Olindo to the Hard Rock Hotel and Casino in Biloxi, Mississippi for a break from her studies. At the time, Olindo was in grad school at the College of Charleston School of Business.
"Little surprise vacation for this book worm," Conover captioned a photo of them sitting on a plane en route to their getaway.
April 2017: Craig Conover passes the Bar Exam
Naomie Olindo Instagram
After multiple tries, Conover passed the Bar Exam to become a lawyer. Conover's long journey to pass the notoriously difficult legal test had been chronicled over several seasons of Southern Charm, so viewers — and Olindo — were excited for the reality star to become a practicing attorney.
"Can't believe this cutie passed the BAR!!! Well I can...but still excited," Olindo captioned a since-deleted Instagram post.
August 22, 2017: Naomie Olindo posts her last Instagram photo with Craig Conover as a couple
"No matter how many times we told @caconover not to look at the sun without his glasses, he looked at the sun without his glasses," Olindo captioned the last photo of her and Conover as a couple that appeared on her Instagram feed. The image was captured while the pair were on a boat in Charleston Harbor.
September 2017: Craig Conover and Naomie Olindo break up
Paul Cheney/Bravo/NBCU Photo Bank/NBCUniversal via Getty
Conover and Olindo parted ways in September 2017. Olindo confirmed the breakup on Instagram when she responded to a fan who asked if her and Conover were still together. "Unfortunately we are not. But we are still great friends," Olindo wrote.
Viewers learned more about the pair's split when Southern Charm returned for season 5 in 2018.
RELATED: Southern Charm's Craig Conover and Naomie Olindo Break Up: 'We Are Still Great Friends'
"Naomie and I, we had the best of intentions," Conover said in a 2018 interview with Bravo's The Daily Dish. "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. 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. It was just kind of disappointing and sad."
Olindo echoed Conover's reasons for their breakup in a separate interview with The Daily Dish.
"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," she said "It was sad because we did care about each other. You saw, we just could not get along."
May 2018: Craig Conover reacts to Naomie Olindo going Instagram official with her new boyfriend
Olindo went Instagram official with her new boyfriend, Metul Shah, in April 2018 when she posted a photo of the two of them arm-in-arm with the caption, "Pray 4 him." Southern Charm fans would later see the early days of Olindo and Shah's relationship play out on season 6.
Olindo spoke to PEOPLE the following month about her new relationship, saying, "I'm very, very happy. He's wonderful."
As for where she stood with Conover, the reality star said that the pair was in a good place after their messy split.
"We definitely both wish each other the best," she said. "We understand why it didn't work out, and it's time to move on and just be happy for each other. It's a good thing."
Conover also spoke to PEOPLE around the same time about his former girlfriend's new romance, saying, "I'm happy for her."
"I knew him before," he continued. "It's what she wanted. She wanted someone with, like, a very structured job, with a real job."
"Her making it official was weird, but they had been together for a while," Conover added, before saying, "As long as she stays out of my life, then I'm happy for her. I just don't want her getting involved with anything I'm doing."
October 2020: Craig Conover goes public with Natalie Hegnauer
When season 7 of Southern Charm aired in October 2020, viewers learn that Conover fell in love with his new girlfriend, Natalie Hegnauer, while isolating at home together during the summer of 2020. The pair first met in Aspen in January 2020.
"We were stuck in quarantine and kind of shielded from the world," Conover said in an interview with PEOPLE. "And it was a lot of fun. I know for a lot of people, it added stress to the relationship, but for us, it made us closer."
May 2021: Craig Conover confirms he and Natalie Hegnauer broke up
After fans began to speculate that Conover and Hegnauer had broken up, Conover confirmed the pair had split during an episode of his podcast Pillows and Beer in May 2021.
"It's good because my parents were here this week and I was in … Because I'm going through, like, [a] break up, and it's nothing terrible, it's just so easy to drink to avoid dealing with anything," he said.
July 2021: Naomie Olindo and Metul Shah split up
In July 2021, Olindo and her boyfriend of three years called it quits weeks after moving to New York City together.
"Naomie and Metul are no longer together," Olindo's agent Paul Desisto told PEOPLE. "She is back in Charleston and plans to stay there for the time being."
Olindo later addressed the breakup on her Instagram Story, revealing that she found out via social media that Shah had been cheating on her.
"Nothing will be worse than losing my dad but this is a close second," she wrote along with a teary-eyed photo of herself. "Betrayal is never easy for anyone and I'm just so sorry to anyone else who has stumbled across those terrible messages."
October 2021: Craig Conover makes his relationship with Paige DeSorbo public
Conover and fellow Bravo star Paige DeSorbo fueled relationship rumors after filming Summer House together in June 2021. They confirmed their relationship status four months later.
RELATED: Paige DeSorbo and Craig Conover's Relationship Timeline
"It was done in a healthy way," Conover said in an interview with PEOPLE. "We built a friendship and got to know each other first, and it all happened naturally. You see the foundation of our relationship start to form on [Summer House]."
October 26, 2021: Craig Conover gives an update on Naomie Olindo after her breakup with Metul Shah
During an appearance on Watch What Happens Live with Andy Cohen, Conover offered an update on how his ex Olindo was doing after her public split with Shah.
"I think she's relieved in a weird way," he said. "She's happy to be back in Charleston."
Conover added, "I don't think she was that happy in her relationship, and I think she's just happy to be living her own life again."
February 2022: Naomie Olindo says she had to "beg" to get back on Southern Charm
Following her split with Shah and her move back to Charleston, Olindo decided to return to Southern Charm for the show's eighth season. But as she revealed on Dear Media's Skinny Confidential Him & Her podcast, she wasn't exactly welcomed back with open arms.
"I had to, like, beg my way back," Olindo said. "I was like, 'Guys, please. I know I quit and I know I told everybody to f--- off, but please I'm very depressed and I really want to come back. I don't know what I'm going to do if I'm back in Charleston.' They were like, 'All right.' "
March 2022: Craig Conover reveals he was a "big proponent" of Naomie Olindo's Southern Charm return
While appearing on Watch What Happens Live alongside DeSorbo, Conover was asked by host Andy Cohen whether he was "upset" that Olindo was returning to the series.
"No, I was actually a big proponent of it," he said. "She came clean about everything. She apologized to everyone that she needed to."
Conover also revealed that Olindo had "said everything that everyone has always wanted her to say to me."
"She said she was sorry. She was honest about it," he continued. "… It brings it all home and I think people are really going to enjoy this season."
March 29, 2022: Craig Conover discusses his relationship with Naomie Olindo in his memoir
Craig Conover Instagram
Conover's debut memoir, Pillow Talk: What's Wrong with My Sewing?, was named after a famous scene in Southern Charm season 5, when Olindo critiqued him for spending too much time sewing, to which Conover responded, "What's wrong with my sewing?"
Despite breaking up years earlier, Olindo agreed to be interviewed by Conover's collaborator for the book. "I didn't think it was appropriate to tell our story without her involvement," he said in an interview with PEOPLE.
Conover also said the most difficult chapter to write was the one that addressed his relationship with Olindo. "I really looked in the mirror for the first time," he said. "I've been honest with myself about the breakup but there were so many layers to it."
The reality star also spoke candidly in the book about his Adderall addiction and how it impacted their relationship.
"I was able to not address it for a long time, but writing this book was basically one long therapy session of finally telling the truth to myself," he told PEOPLE. "There were a lot of things about our relationship that people didn't know about."
May 16, 2022: Southern Charm fans learn that Craig Conover and Naomie Olindo hooked up after their breakup
Bravo
When the Southern Charm season 8 trailer dropped in May 2022, fans learned that Conover and Olindo had more recent history than they thought.
"We're not just exes," Conover said to Olindo in the preview. "We hooked up recently."
DeSorbo corroborated this claim in early May during an appearance on Watch What Happens Live with Andy Cohen.
"OK, I'm gonna be totally honest," DeSorbo said. "I feel like if you're gonna hook up with your ex-girlfriend, you should do it in Vegas. 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."
June 2022: Naomie Olindo opens up to PEOPLE about her hookup with Craig Conover
Ahead of the show's season premiere on June 23, Olindo opened up to PEOPLE about her hookup with Conover, adding that reviving her relationship with him was never on the table.
"Neither one of us ever thought we would get back together," Olindo said. "This happened a year ago now and it was sort of a one or two-off situation where you just know each other and you're comfortable around each other and you have some fun."
"It was almost like, a bit of closure at the same time, because we had been together for so long and now we finally had a friendship again now that so much time had passed," she said. "But really, it was nothing more than that."
June 30, 2022: Craig Conover says reconnecting with Naomie Olindo showed him he's "not into this anymore"
Charles Sykes/Bravo/NBCU Photo Bank/NBCUniversal via Getty; Jeff Kravitz/Getty; Amy Sussman/Getty
During an episode of Southern Charm, Conover confirmed that his Vegas hook up with Olindo gave him closure on their relationship.
In a flashback from Kathryn Dennis's eventful Great Katsby 30th birthday party, Conover recounted the former couple's reunion with his friends, saying, "I woke up and I was like, I'm done. I was like, I'm not into this anymore."
Conover and Olindo also discussed their hook up during the episode, with Conover assuring her they had an "amazing experience."
"I don't have any regrets about it," he said. "I love you to death and you know that. You know I'll always feel that way about you. I wish you would've gotten to know me, like who I am today. You would've liked the guy."
August 11, 2022: Craig Conover says Naomie Olindo isn't "respecting boundaries" with him and girlfriend Paige DeSorbo
During another Southern Charm episode that aired on Aug. 11, 2022, Olindo experienced tension with Conover at Patricia Altschul's dog wedding, where Altschul's pooch, Peaches, "wed" Shep Rose's pet, Little Craig.
Conover's girlfriend, DeSorbo, showed up at the rainy wedding in a mini dress, so Olindo insisted Conover offer DeSorbo his jacket.
"What is going through Naomie's head where she thinks that she knows what's best for me and my girlfriend?" Conover asked the cameras. "I don't think she's getting it. Like, this is not respecting boundaries."
"I feel awkward around Craig now," Olindo admitted to LeCroy and Venita Aspen. Olindo later pulled Conover aside to confront him about how he acts differently when DeSorbo is around.
"The only thing I was trying to ask you is if I make you feel uncomfortable in the way that you made me feel uncomfortable when I was dating Metul," she said.
Conover did not appreciate the comparison to Olindo's former relationship.
"You left a loving relationship to be with a controlling a--hole who cheated on you," he told her. "In the meantime, your boyfriend that loved you for a long time moved on so you can never compare the position that I'm in with a very loving girlfriend with the position you were in."
