When Molly O’Connell first revealed her new “taken” relationship status during a Dec. 2025 appearance on Watch What Happens Live with Andy Cohen, she shared a few details about her musician boyfriend. During the Southern Charm Season 11 reunion, she opened up further about her love life, including revealing a large age gap between herself and her partner.
“He’s a musician in Charleston,” Molly divulged during the March 18 episode. “He’s extremely talented… He’s 56, and I’m 38. I like a little seasoning,” she joked.
In Dec. 2025, Molly told The Daily Dish she’d been dating the mystery man “for the past few months.” At that time, the singer and euphonium player revealed that her partner is a guitar player.
“They’re in a band together. That always works, right?” Shep Rose, who was seated alongside Molly for the Dec. 2025 WWHL appearance, joked.
Andy Cohen cheekily replied, “I might put more money on it working than the two of you, with all due.”
Molly O’Connell’s previous fling with Shep Rose, explained
Andy, of course, was referencing Shep and Molly’s brief fling, which was featured on the Southern Charm Season 10 finale, when they shared a passionate kiss. They admitted to “some adult fun” after the on-camera smooch, and, during the Season 10 reunion, Andy asked Molly if Shep left her “satisfied,” to which she replied coyly, “I had fun.”
Shep shared that the relationship fizzled when he “left town” for the “summer and most of fall.”
RELATED: Shep Rose Reacts to Molly O’Connell’s Crush on Him: “She Doesn’t Hold Anything Back”
At that time, Molly didn’t rule out a future relationship with Shep, despite what Andy called his “track record” with women. “We all do weird s—t,” Molly said to defend Shep. “If I see someone actively working to better themselves, I think that’s more than a lot of most people do, and I appreciate that.”
But Molly shared that the dalliance was officially over by BravoCon 2025 in November.
“I think we are just better as friends,” Molly told Entertainment Tonight at that time. “I think on paper, all of it makes sense, but it’s Shep at the end of the day. But I love Shep. He’s so much fun. We had a fun time — a good time, not a long time.”
Molly O’Connell’s romantic connection to Winter House’s Kory Keefer
After her time with Shep, Molly enjoyed a flirtation with Winter House alum Kory Keefer, which played out during the Southern Charm Season 11 premiere. Kory joined the group at Madison LeCroy’s baby shower, and his chatting held Molly up from her Charleston Concert Band practice.
RELATED: The Southern Charm Guide to Dating in Charleston: Advice From Craig, Austen, Madison & More
“Kory’s a huge flirt,” Molly confessed to producers during the Nov. 19 episode. “I mean, he’s hot in like a … f–kboy way.” But she later lamented that his “toxic” ways were working on her. “My therapy apparently is not working very well if this is who I think is cute,” she added.
Although Madison noted Kory and Molly looked “really cute” together, and Craig Conover gave his approval, their interaction died out.
“We’re friends. We haven’t really hung out or anything,” Molly said of Kory during her Dec. 10 WWHL appearance. “It was really just a very short flirtation.”
Catch up on Austen Kroll’s reveal that he was also interested in Molly and “flirting” with her during the cast trip to Mexico.
