Talking about money early in a relationship can feel daunting. Money is often rooted in fear and shame, which can make intimate conversations uncomfortable, especially when you’re still trying to keep things light and fun.
However, as a family law attorney for nearly a decade, during which time I have represented high-net-worth clients through cohabitation, marriage, kids and divorce, I can attest to the value of gauging your potential partner’s money values early on. I’ve seen how financial conflict can erode even the strongest relationships. Too often, couples never talk about money and they pay for it later.
I’m not saying you should ask your date about their 401(k) balance on the third date. But there are five essential questions you should ask by this point. That way you can spot any red flags before your heart is in too deep.
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"Celebrity Divorce Attorney: Ask 5 ‘Essential’ Money Questions by the Third Date: ‘Spot Red Flags Before Your Heart Is in Too Deep,’" by Jacqueline Combs was published in CNBC Make It on August 25, 2026.