205. “I've been homeless before…I'm terrified to spend money”

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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