Tuesday, October 14, 2025

Dave Ramsey Caller Has ‘Been Asleep At The Wheel’ And Racked Up $230,000 In Debt. His Millionaire Girlfriend Won’t Marry Him Until He Pays It Off

A caller to “The Ramsey Show” recently revealed that his mounting debt is delaying his plans to marry his financially successful girlfriend. Joe, from Milwaukee, told Dave Ramsey and co-host Ken Coleman that he’s only recently come to terms with the reality of how much he owes.

Millionaire Girlfriend, Six-Figure Salary And A Massive Debt Problem

“I started digging into the numbers and found out what I really owed,” Joe said. “Kind of spooked me a little bit. Wasn’t quite as—was a lot more than I thought it was.”

Joe admitted to owing around $230,000 in total debt, including $180,000 in student loans and $34,000 on a car. He said he used the loans to complete a master’s degree and is now working on a business Ph.D., hoping to teach and coach golf in college. In the meantime, he works in retail management and earns $120,000 a year.

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His girlfriend, on the other hand, is in a much stronger financial position. Joe said she has a net worth of about $1 million and earns $160,000 annually. She’s “not quite 40” and has started asking him questions about investing. That’s when Joe said he realized how financially misaligned they were.

“I hope that we’re together forever. I don’t ever want to put her in a bad position,” he said. Joe floated the idea of a prenuptial agreement, but admitted they were still early in those discussions. “If some crazy reason it doesn’t [work out], I would hate for, like, you know, to feel like I’m supposed to get half of your stuff when I’m coming in with nothing and you’re coming in with a lot.”

Ramsey didn’t think a prenup would fix anything. “If you’re going to share a bed and a life together for the next 50 years, you’re going to share assets and liabilities for the next 50 years,” he said.

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The hosts were more concerned with Joe’s delayed realization. “You’ve been asleep at the wheel for quite a while and just in the last few weeks woke up,” Ramsey said. “What scares me more than the debt is that you just now woke up.”

Ramsey said he’s never advised someone not to get married because of debt, but he has told people to delay marriage until they align on values like career goals, saving, and financial priorities.

As for the girlfriend, Joe said she’s open to waiting. “She just said she understands it may take a little while to be able to pay this stuff off. So if it takes a while and we have to wait, then that’s fine,” he said.

Coleman and Ramsey advised Joe to get aggressive about paying off the debt and show he’s serious about change. Once married, Ramsey added, they could write checks and wipe out the remaining debt, but only after Joe proves he’s turned the corner.

“Your debt should be largely gone by then because it’s going to take a little while for you to prove to her that you’re awake,” Ramsey said.

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