November 19, 2018 05:35 PM

Luke Bryan‘s wife Caroline was the breadwinner in the household before he got his career off the ground.

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.

Caroline and Luke Bryan
Jason Kempin/Getty

“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.

Luke Bryan, Kellie Pickler and Ben Aaron
George Burns, Jr.

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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.”

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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.”

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“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.”

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