205. “I've been homeless before…I'm terrified to spend money”
Apr 22, 2025•1 hr 19 min•Ep. 205
Episode description
Jennifer (37) and Steve (41) have been dating for over five years, but they’ve never spent more than $100 on a shared purchase.
Jennifer is a self-made business owner with a clear vision for the future, while Steve is cautious, financially conservative, and still haunted by a turbulent past that included losing both parents and living out of his car. Despite a solid income and nearly $200,000 in savings, Steve can’t shake the fear of financial collapse. Jennifer, meanwhile, is growing resentful. She wants a partner who dreams big and makes bold moves with her—not someone who second-guesses a $10 purchase.
Can they confront the past, align on a shared vision for their future, and finally start acting like teammates?
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Links mentioned in this episode
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