When dating starts to turn toward commitment, everybody asks this simple question: how much debt do you have? And surprisingly, that is one of the least useful questions you can ask someone about their finances, and there are two things that actually predict trouble that are not numbers at all. When we got engaged, we had student loan debt, no careers, and zero assets. And unlike many younger couples today, we never had a formal money talk. Thirty-one years later, we are on a solid foundation, which either means we got super lucky or it means the debt number was never really the most important thing we learned about each other before getting married. In this conversation, we discuss what recent surveys uncover about money and dating, confess our lack of money talks early in our relationship, and we explore how we do it differently if we were starting over. What you will hear: Why asking for your partner's debt number is a weak signal when learning your partner's money habitsThe two financial red flags that ranked above credit card debt in a national survey, and why both signaled character over numbersHow debt as a dealbreaker is viewed differently based on how you ask the questionWhy many people don't discuss finances until becoming exclusive, and those with the most debt wait the longestThe five signals that tell you more than just a debt number: amount, type of debt, direction, philosophy, and risk appetiteWhy secrecy is the true financial dealbreaker in relationshipsThe rise of online sports betting and crypto as financial risk categoriesPractical takeaways we share:Two questions that reveal money character better than just a debt number: what does abundance look like to you, and what does scarcity look like to youAsking about a purchase regret, and why the answer tells you how someone learns from their pastAssessing risk tolerance by asking: what is the most money you have ever had riding on something uncertain, and how did waiting feelHow to recognize a misalignment you can work on versus a misalignment your partner refuses to discuss Pen to Paper:To help you learn more about your partner's money character, start by asking this question: how was money handled in your family when you were growing up? Who paid the bills, who kept track, and was money talked about openly or not at all? What someone watched at home is one of the better predictors of how they will handle money with you. If you are dating someone seriously, thinking about getting engaged, or sitting on a money conversation you keep putting off, this is the episode you cannot afford to skip. Chapters00:00 Is debt a dealbreaker when you're dating?02:31 What the 2026 dating and money surveys found03:34 The two red flags that beat credit card debt06:35 Why most people wait too long to talk about money08:33 Why merging finances early is the top dating red flag09:42 The money talk we never had before we married14:13 What to ask instead of what's your debt number15:17 Why the direction of someone's debt matters more16:09 Does your partner see debt as a tool or a trap17:05 Crypto, sports betting, and reading risk appetite20:35 Ask about abundance and scarcity to reveal money character24:13 The purchase regret question and what it reveals27:55 A risk question that gets past the dollar amount29:55 Why people hide their numbers from a partner33:23 Financial secrecy in relationships is a red flag35:04 Ask how money was handled in their family38:51 Why the money conversation cannot wait 📊 Sources referenced in this episodeThe Harris Poll, Modern Dating Survey, February 20262,177 U.S. adults surveyed January 22 to 24, 2026, including roughly 780 singles Earnest, Debt and Dating Research Report, published February 3, 2026More than 1,100 people surveyed Northwestern Mutual, 2026 Planning and Progress Study, conducted by The Harris Poll JOIN the Penned in Ink Community for UpdatesWATCH on YouTubeConnect with Us on Instagram
