This week on The Pete the Planner Show, we’re tackling one of the toughest money dilemmas families face today: when helping your adult children turns into hurting yourself. A listener writes in about her 31-year-old daughter who still lives at home, contributes nothing financially, and has become the center of a tug-of-war between supportive love and enabling behavior. Pete, Kristen, and Damian unpack the concept of financial enmeshment—those blurred parent/child roles where support becomes indefinite, boundaries vanish, and retirement plans quietly suffer. Why is this happening more than ever? Sky-high housing costs, student debt, and the return of loan payments all play a role, but so do fear, guilt, and a desire to shield kids from failure. We’ll explore the emotional conflict between partners who disagree on rules, the hidden cost of Parent PLUS loans, and why “support without structure is just deferred conflict.” Then, we’ll lay out practical tools for parents: aligning as a couple, having honest conversations with adult kids, and creating a phased transition plan that respects both love and limits. If you’ve ever wondered where generosity ends and enabling begins, this is an episode you won’t want to miss.