Ramit unpacks whether Randy can move toward marriage while Mack brings $100,000 of debt into their future together and whether that debt could become a problem they both have to live with. Randy and Mack are in their early 30s, and are talking seriously about marriage. But their financial lives look completely different. Randy has a net worth of around $102,000, while Mack is at roughly negative $56,000, largely because of $100,000 of debt. Randy feels increasingly “handcuffed” by what that debt means for their future, while Mack worries that he has gone from being supported to becoming a problem to solve. Ramit quickly discovers that the real issue is not simply the debt. Mack already has an aggressive payoff plan that could make him debt-free in under four years. The deeper problem is trust, avoidance, and the way they manage money as a couple. Ramit helps them rethink their 50/50 split, build a more equitable system, and create a plan where Mack takes ownership of his debt while t...