For one California father facing terminal cancer, that question came with an unexpected twist: he just won $100,000 in a fantasy football contest. Unsure how to handle the sudden windfall, he turned to financial expert Dave Ramsey for guidance (1). And in a rare moment, Ramsey, usually quick with an answer, fell speechless.

After hearing William reveal his financial situation, Ramsey replied, "You're a good freak," after the caller confirmed he has a net worth in the $10 million range. While Ramsey pointed out that prenups are rarely needed, he said they make sense when one partner enters a marriage with significantly higher assets.

For many Americans, the decision to claim Social Security at 62 feels like a race against the clock, not a long-term financial strategy. Dave Ramsey argues that the real "winner" in that race is not the person who files the earliest,

Thomas, who is an active duty member of the military, called in to the show seeking advice after racking up about $57,000 in debt following his divorce. His debt includes about $37,000 on a truck that he purchased after the divorce, as well as roughly $18,000 in credit card debt (1).

A 28-year-old caller from Vancouver joined "The Ramsey Show" with a housing dilemma that quickly became a lesson in personal finance denial. Alexandria said she was living in a dark, windowless basement suite that was taking a serious toll on her mental health.