216. I track every penny. He gambles. Should I marry him?

Taylor (29) is a high-earning dentist with a strict savings plan and deep-rooted fears about financial instability. Hayden (25) earns $24K a year, has a history of gambling and financial dishonesty, and struggles with budgeting. They live together, but their vastly different money philosophies leave Taylor questioning whether marriage is possible. With trust issues, income imbalance, and emotional baggage on both sides, can they find common ground—or is it time to walk away? In this episode we uncover: • Taylor’s strict financial boundaries—and why Hayden feels constantly judged by them • The real reason Hayden hides purchases (and what it’s costing their relationship) • Why Taylor resents being the financial provider, and how it’s creating a growing power imbalance • A candid conversation about Hayden’s past gambling—and whether trust can be rebuilt • How their radically different upbringings shaped two completely opposing money mindsets • The unspoken tension around engagement...