Dating, Dollars, and Deal-Breakers: Why Talking About Money Might Save Your Relationship
Everyone knows that marriage requires trust, communication, and shared values. But there’s one topic that often gets pushed aside until things get serious—or worse, until there’s a crisis. Money.
It’s not because people don’t care about financial compatibility. In fact, they care deeply. But many don’t know how or when to bring it up. I spoke with Aleeza Ben Shalom, Netflix star of Jewish Matchmaking, matchmaker, coach, and host of the popular podcast, Matchmaker, Matchmaker, about what she sees time and again in dating and marriage: People avoid talking about money because they’re afraid it will cause tension. But avoiding it only delays the inevitable.
The real secret? Conversations about money don’t have to be awkward. They can be meaningful, respectful, and even eye-opening.
What financial personality really means
Every person has a “financial personality,” even if he never learned how to label it. Some people feel secure when they save. Others need to spend to feel free. Some invest without blinking. Others hesitate at every small risk.
If someone wants to build a strong relationship, whether it’s new or decades old, it helps to understand the other person’s style. Is she generous with gifts? Is he worried about retirement? Does she know what’s in her investment portfolio, or has she left that to someone else for years?
These questions aren’t just about money. They’re about how someone makes decisions, handles pressure, and plans for the future. And especially when living in Israel while managing U.S. accounts, it takes awareness on both sides to stay financially aligned.
Second marriages, separate accounts, and sticky situations
When someone gets remarried, the conversation shifts. Now there might be children from a previous marriage. There could be an inheritance or a home bought long before the new relationship began. In these cases, transparency becomes even more important.
Aleeza told me about people who hesitate to talk about assets or prenups because they think it suggests a lack of commitment. But experience shows the opposite: Not talking about finances creates more problems, not fewer.
In one case I’ve seen, a woman inherited money from her parents, remarried, and later found herself stuck. When the relationship ended, her new husband wouldn’t give her a get unless she gave him part of the inheritance. She never imagined money would be used as leverage, but it was.
These are the kinds of challenges that can be avoided with conversations early on. Not to test someone’s loyalty, but to clarify expectations and protect what’s important.
How to talk about money (without making it weird)
Aleeza recommends starting easy. Instead of asking about bank statements or retirement accounts, ask questions that reveal values. “If you got a million dollars, what would you do first?” “What’s your favorite thing to splurge on?” “Did your parents talk about money when you were growing up?”
These kinds of questions don’t just uncover surface-level preferences. They open the door to deeper conversations and reveal underlying patterns. Over time, the two people in a relationship can develop a shared language around money, which becomes essential when facing major decisions together.
No one needs to have it all figured out. But by being curious and staying open, a couple can build the kind of financial intimacy that supports a lasting partnership.
Want to start better conversations about money with less stress? Check out Financial Date Cards at www.financialdate.com and explore real questions that matter, without pressure or awkwardness.
And if you’re managing U.S. investments while living in Israel, schedule a free Cross-Border Financial Evaluation to make sure your financial strategy supports your relationship goals.
For more information on Aleeza Ben Shalom visit her website at marriagemindedmentor.com.
