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—and what’s holding Taylor back from proposing • Taylor’s biggest fear: ending up broke and alone • Hayden opens up about insecurity, dependence, and feeling “less than” • What they really want from each other—and why neither feels safe enough to ask Chapters: (00:00:00) “He gets to do whatever he wants with his money” (00:07:22) Ramit breaks down their numbers (00:20:58) “Why have all that money if you don’t plan to spend it?” (00:28:27) How childhood trauma shaped their views on money, control, and survival (00:37:44) A secret $35K loss—and the fallout that nearly ended everything (00:49:15) “Most of what I do with money is to get her off my back” (01:01:12) Is change still real if it’s only for someone else? (01:03:56) A new plan, a new mindset—but will it stick? (01:13:36) Where are they now? Taylor and Hayden’s follow-ups This episode is brought to you by: Upwork | Visit https://upwork.com to post your job for free and connect with top talent ready to help your business grow. Facet | Facet is waiving their $250 enrollment fee for new annual members, and for my audience, Facet is offering $300 into your brokerage account if you invest and maintain $5,000 within your first 90 days. Head to https://facet.com/ramit to learn more about which membership option is best for you. Netsuite | Download the free e-book 'Navigating Global Trade: Three Insights for Leaders' at https://netsuite.com/ramit Fabric by Gerber Life | Join the thousands of parents who trust Fabric to protect their family. Apply today in just minutes at https://meetfabric.com/ramit . Masterclass | For unlimited access to every class and 15% off an annual membership, go to https://masterclass.com/ramit Links mentioned in this episode • Get my 4 simple rules for talking with your partner about money Connect with Ramit • Get my new book, Money For Couples • Get Money Coaching with Ramit • Download the Conscious Spending Plan • Listen to my book—now on Audible • Get my New York Times best-selling book • Get my no-numbers journal • Other episodes • Instagram • Twitter • YouTube If you and your partner have a money issue and you want my help, I occasionally select a couple to work with, free of charge. Apply for my help here .