
220. “I carry the baby, the bills, and the stress”
Monica (36) and Michael (33) have been married just over a year and are navigating the pressures of new parenthood—but Monica feels like she’s doing it alone. She pays the rent, covers childcare, and ...
5 Aug 20251h 35min

219. “He’s so cheap it’s killing our joy”
Angela (52) and Brian (52) have been together since they were teenagers and have raised four kids. Now as they approach being empty nesters, they’re stuck in a sitcom-style standoff: Angela loves bar...
29 Jul 20251h 21min

218. “Our childcare costs are about to quadruple. Are we screwed?” (Part 2)
Last week, we met Dominique (33) and Chris (34)—a couple earning $180K a year, raising a toddler, and still living paycheck to paycheck. Dominique felt alone in managing their finances, while Chris st...
22 Jul 20251h 2min

217. “Are we broke…or just bad with money? (Part 1)
Dominique (33) and Chris (34) have been together for six years, engaged for two, and share a two-year-old son. While Dominique manages parenting, full-time work, and their finances, Chris shuts down w...
15 Jul 20251h 21min

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, a...
8 Jul 20251h 15min

215. “He wants a house, I don’t want to go bankrupt.”
Athena (31) and Arie (30) are newly married and dreaming of buying a home, starting a family, and traveling the world. But their finances—and philosophies—don’t align. Athena’s upbringing was defined ...
1 Jul 20251h 33min

214. “I’m 45 but my parents still control my money”
Kate and Keith have spent years afraid to spend—until now. In Part 2 of this conversation, Ramit investigates the $5 million missing from Kate’s trust fund and uncovers decades of poor returns, excess...
24 Jun 202558min

213. “We have a $1M trust - but a $30k budget” (Part 1)
Kate (45) and Keith (53) split their time between Maine and Hawaii, living what looks like a dream life. They’ve inherited wealth, run two small businesses, and have nearly $2 million in net worth. B...
17 Jun 202559min




















