Courtney Swindell's first date with her now-husband, country superstar Cole Swindell, didn't quite go as planned.

Courtney caught up with Hanley Riggs on a new episode of Married to the Musicon Friday (October 23). The pair talked about Courtney's "North Carolina roots, cheering with the Hornets Honeybees, traveling with Monster Energy, and learning how to navigate airports and tour buses," throughout the podcast. During the conversation, Courtney reflected on her first date with Cole.

The couple first met at a NASCAR event, and Cole invited Courtney to appear in his "Some Habits" music video in 2021. The video served as an unofficial "first date," and they planned to go out afterward.

"The funniest part is that it was kind of during Covid. It was 2021. So, I feel like everything was still kind of shut down," Courtney said. She'd asked Cole to take her to a place "that nobody goes," rather than some of the tourist spots in Nashville, Tennessee. "He really didn't go out. I didn't know that though.

"Every place he took me was closed [because of Covid restrictions]," Courtney continued. "You can tell he's so nervous because he's like, 'Oh no, that one's closed, too.' So, we found this random place and they're like, 'We have two seats right no,' and so we were like, 'Perfect. Let's go.'"

Cole popped the question in May 2023 (Courtney also reflected on the "very sweet" proposal on Married to the Music). He and Courtney said "I do" in a stunning, intimate wedding on June 12, 2024, in Sonoma, California, and later hosted a surprise wedding reception for about 250 guests when they returned to Tennessee. Cole and Courtney welcomed Baby No. 1, daughter Rainey Gail Swindell, in August 2025. The country star said at the time that his daughter is "our greatest blessing."

Listen to Courtney's full conversation with Riggs on Married to the Music on iHeartRadio, or watch here.