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Craig Conover’s evolutionary journey on Southern Charm has seemingly come full circle now that he’s moved from playing an annoying little brother-type role to a leading man on the series.

In 2014, Bravo fans met Conover, a wet-behind-the-ears law student, who found himself in an exhausting loop of trying to keep up with Charleston’s version of the Kardashians.

Old money sons like Shep Rose, Whitney Sudler-Smith, and Thomas Ravenel often dragged Conover for his career choices. His decision to temporarily shelve his pursuit of a law career for gardening and sewing annoyed and frustrated everyone around him, including ex-girlfriend Naomie Olindo.

Meanwhile, darker forces were at work behind the scenes, when Conover later admitted he was addicted to the ADHD medication Adderall, which often shaped his decision-making and behavior.

From pillow fail to pillow king: Craig Conover proved everyone wrong on ‘Southern Charm’

Conover had some dark days when Olindo left him and he struggled to find his way down the career path. He had lied to his friends about getting a law degree and still needed to finish law school. Meanwhile, he stumbled and sputtered while trying to shape his career vision.

Cast photos of Craig Conover from Southern Charm plus Patricia Altschul holds a pillow in front of Craig Conover
Craig Conover, Patricia Altschul |Charles Sykes/Bravo/NBCU Photo Bank via Getty Images/Robert Ascroft/Bravo/NBCU Photo Bank/NBCUniversal via Getty Images/Brianna Stello/Bravo/NBCU Photo Bank via Getty Images

His infamous meeting with Patricia Altschul was a fail when she gave him the opportunity to design pillows for her company. Not only was he late for the meeting, but she observed that the designs he presented were created from clip art. She sent him packing feeling defeated.

And while fans saw him at his low point, he rebounded and soared further than what anyone could have imagined. With the help of some friends – who were not on Southern Charm – he quietly launched a small textile company, Sewing Down South.

Conover talked about his new venture with Showbiz Cheat Sheet in 2020, optimistic about opportunities on the horizon. He laughed thinking back to how his friends gave him such a hard time about his sewing (what’s wrong with my sewing?).

“Shep finally had to accept the fact that I’m never going to be the type of person he wanted me to be,” he said. “But he loves it now. What he said is ‘All I ever wanted was for Craig to be honest with himself.’”

He added, “But it’s funny. Our message is of positivity so it’s fun to get the last laugh.”

Craig’s Adderall addiction was a big reason why his relationship with Naomie crumbled

When Conover spoke to Showbiz Cheat Sheet in 2020, he was still raw from his breakup with Olindo. But he observed how she took note of his rise from the ashes. “She has been incredibly nice and supportive,” he recalled at the time.

“We got to talk about relationships and what we’ve taken out of ours,” he said. “And it was just funny. It was nice. Was one of the first times that we’ve talked, as, you know, completely as friends. And she was super nice about that. I thought she [talked about our friendship] in interviews. She said she always be grateful for the world that I brought her into it. She was happy for [Sewing Down South] and everything is all very positive now.”

Conover and Olindo both recently revealed that one of the biggest reasons why they broke up was because of Conover’s Adderall addiction. “That was a big part of our problem,” Olindo recently told Showbiz Cheat Sheet. “It was that he was talking like a bunch of Adderall and he would stay up all night. But not do things that he was supposed to be doing because he was just like kind of cracked out at the time.”

Craig kicked his Adderall addiction and is in a loving relationship

Conover hinted about his addiction to Adderall on Southern Charm but came clean about how bad it was in his book, “Pillow Talk: What’s Wrong with My Sewing?” He recently told Showbiz Cheat Sheet he started chasing meds on the street.

“I was prescribed two 20s (mg), which was too much. So I would break them into 15s for years. Which meant I was taking under my dose. Then I started taking that third dosage in the afternoon or that evening. Then I kind of just went from there. And then all of a sudden, I was running out by the end of the month, which was not a great feeling.”

While Conover used to go on and off the medication, he’s since completely stopped taking Adderall. He told People, his biggest struggle now is finding balance. “Balance, I’ve never found,” he said. “I don’t have a balance. No matter how many people want to tell me that there’s balance, for me there’s not. I’m either not doing s*** or I’m doing well. There’s no middle ground. One day I hope to find balance, but until then, I just have to keep momentum going in a good way.”

In addition to getting his law degree and passing the bar, Conover has opened his own law firm, has grown Sewing Down South into a national brand and is in love. He is dating Paige DeSorbo from Bravo’s Summer House, who he got close to while filming Winter House. They started dating last summer and are now talking about marriage. He recently said in a confessional on Southern Charm: “Paige loves me for who I am, and I love that feeling. She’s my biggest fan. And I think that’s something that I’ve been looking for for a really long time — forever.”

How to get help: In the U.S., contact the Substance Abuse and Mental Health Services Administration helpline at 1-800-662-4357.