On Monday’s episode of Pickler & Ben, the “What Makes You Country” singer, 42, explained how the couple’s financial setup looked while he was first trying to make it as a songwriter. “When we got married, her career supported me when I was making about $10,000 a year,” he revealed. “She was the one bringing in the dough.”
Bryan recalled the on-again-off-again relationship that he and Caroline — who share sons Tatum “Tate” Christopher, 8, and Thomas “Bo” Boyer, 10, and took in Bryan’s nephew and nieces — had before they tied the knot.
“We’d date a little in college, and then we’d break up,” he explained. “And then I would be devastated. We’d get back together, break up. Then she would be devastated.”
“We finally decided we were not going to break up anymore. And then I graduate college, and she has two more years, and then we break up again. It was like the Dark Ages for both of us,” Bryan continued.
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“And then we were apart for 5½ years, which was kind of a blessing because I went off to Nashville, got all this going,” the American Idol judge said. “She finished college. She went and actually had a career.”
Of course, Bryan’s more than made it up to Caroline since — upgrading her engagement ring as they celebrated a decade of marriage back in December 2016.
“It was a little 10-year anniversary gift. Ten years with me feels like a thousand,” he joked to PEOPLE at the time. “It was certainly the least I could do!”
In 2014, Caroline spilled about the romance — which started when they met at Georgia Southern University — to PEOPLE.
“He was always a gentleman,” she said. “We hung out as friends first and he never made a move on me. I kissed him first! He was always so scared of making a girl feel uncomfortable, he wouldn’t cross a line.”
“In college, we used to go dancing in a club til 4 a.m., and he’s just as silly at home as he is on stage,” Caroline revealed. “He walks around dancing all day, just being goofy.”