Lady A’s Charles Kelley, Cassie McConnell’s Relationship Timeline

Together through it all. Lady A musician Charles Kelley and his wife, Cassie McConnell, have weathered some tough times during their relationship.

During an emotional appearance on CBS Mornings in May 2023, the duo — who tied the knot in 2009 — opened up about how Kelley’s struggles with alcohol addiction had affected their marriage.

“When he was in rehab and I went out there for family week, one of the first messages you receive is, ‘You’re gonna have to do just as much work here.’ And I remember being so mad,” McConnell told host Gayle King.

She continued: “Like, you did this. And now I have to do all of this work too? But … it affects every person in that family system. So, I could’ve chosen not to do the work, but then I have to live with the way that I’ve been affected and unhealed. So, whether Charles and I were in a marriage or not, whether I saw him again for the rest of my life, I still had to deal with what I had gone through.”

The Womanista lifestyle brand founder revealed that she considered divorce after Kelley’s behavior during a past trip to Greece. Although McConnell didn’t specify when the vacation took place, she shared a photo via Instagram in June 2022 of the couple in Mykonos.

Kelley recalled of the trip: “I just turned my phone off in the middle of nowhere and just took off and stayed up drinking with all these random people I didn’t know. We had got in an argument, and I had one of those moments where I just was like, ‘I’m so sick of being told what to do.’”

The next morning, McConnell confronted her husband. “I said, ‘You need help. You have to deal with this,’” she explained. “And he said he knew, and he made a plan with his manager and he flew directly from Greece to treatment. But at that point I fully thought I was flying back to the U.S. I was gonna meet with a divorce attorney, like, that was it.”

Despite her candor about her frustrations, McConnell noted that she was “really proud” of her husband, who celebrated six months of sobriety in January 2023.

“Because he keeps showing up every day, I get to keep showing up every day and our family gets to be intact, so I’m really, really proud of him,” she shared. Kelley chimed in that he “couldn’t do it” without his wife’s support.

The twosome share son Ward, whom they welcomed in February 2016. The “Need You Now” musician told King that his son is “the most important thing in my life” and he was therefore “crushed” by the realization that Ward had noticed his drinking problem.

“Cassie would tell me some stories about … little things that Ward would say that I didn’t even know he was noticing,” he said. “You know, ‘Daddy’s talking a little funny,’ or, ‘You and Daddy argue a lot.’”

Despite their hardships, the duo have shared beautiful moments as well. “The first time I met my wife was, like, it really was true love at first sight,” Kelly told UMG Nashville’s Press Room in February 2018, noting that his bandmate Hillary Scott helped set them up. “I get there, and we just lock eyes the whole night. We’re kind of looking at each other, and we’re like, ‘Holy moly.’ She’s the prettiest girl that had ever paid me any attention.”

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Keep scrolling for a look at Kelley and McConnell’s relationship timeline: