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December 4, 2014

It’s not exactly first-date material, but at some point early on couples ought to start talking about money.

Best if the first discussion happens before the relationship takes a turn for the serious—like moving in together, getting engaged or married, or cosigning a loan. You’d want to know if your steady’s trying to pay off a six-figure law school loan or hasn’t saved a dime towards retirement yet, right?

While we know it’s important, many of us shy away from asking our partners key questions related to savings, investments, debt and credit. More than 40% of couples surveyed by Country Financial recently said they didn’t discuss how they’d manage their money together ahead of tying the knot.

As a society, we’re not especially conditioned to speak intimately about our finances. One report found money to be a tougher topic for Americans to talk about than politics and religion. Plus, if you’re not particularly proud of your financial state, a no-holds-barred discussion may stir up anxiety, embarrassment and fear of rejection.

Here’s how to calmly—and, dare I say, pleasantly—enter this critical conversation into the record in the early stages of your relationship:

Set a Date

My now-husband and I had a money powwow about two years into dating.

Don’t get me wrong: By then, we’d fully observed each other’s spending behaviors and discussed goals (thankfully, with no red flags). But we’d yet to really share specific numbers.

With plans to move in together and cosign a lease just a few months down the road, we figured this was a natural and important time to get into the nitty-gritty.

If you and your mate haven’t come anywhere near this conversation yet, my recommendation is to schedule a time to talk so that your partner doesn’t feel blindsided and so that you can each do a little homework beforehand if need be.

One way to frame your request for a money summit: “I know it’s not the most exciting thing to talk about, but it would make me a lot more comfortable if we could go over our finances together since things are getting more serious. I’m not worried at all; I just think it’s helpful if we share the basics so that we’re both on the same page and can work toward common goals. And I want you to feel like you can ask me anything you want about my finances. I want to be an open book about this stuff because I’ve seen how it can unnecessarily complicate things in relationships.”

Then ask: “What do you think?”

Make an Even Exchange of Information…

To ease any potential tension, my future husband and I decided to meet at a familiar and fun setting: our favorite bar.

We ordered a round (one round only) of margaritas and proceeded to jot down the following on a piece of paper: annual income, bank balances, outstanding loans and credit card balances and approximate credit score.

Then we swapped papers, revealing our details at the same time.

This exercise gave us a simple, quick apples-to-apples comparison and helped us understand our relative strengths and weaknesses.

We discovered that while I had more retirement savings, he had a better credit score. (I was still dealing with the consequences of a late payment on my Banana Republic Card five years prior when I was younger and less vigilant. Sigh.)

You and your partner could try this tactic if you both are straight shooters. But if your sweetie could use some help coming out of his or her financial shell, you might need a softer approach.

…Or, Ease Gently into the Interrogation

Revealing a bit about yourself first may encourage your significant other to talk money.

“Share your feelings and see how he or she reacts,” says Barbara Stanny, author of Sacred Success: A Course in Financial Miracles.

For example, you could start by saying, “I really hate having credit card debt.” From there, you can talk about your personal experience and then ask for your partner’s take.

Or, try the following softball conversation starters which can help you get at hardball answers:

What you really want to ask: “How much do you have in savings?”
Start with: “Would you say you’re more of a saver or spender? Why?”

This helps you figure out habits and behavior, which can be just as telling as actual figures. “Most important, you want to know what are their spending and saving personality is like. For example, how impulsive are they?” says Kate Northrup, author of Money: A Love Story. You can follow up with a question like, “Are you trying to save up for anything major?” This approach can also help you figure out if you share similar goals.

What you really want to ask: “What’s your credit score?”
Start with: “When did you first open a credit card?”

Go down memory lane together to ease into your credit technicals. Talk about how you might have signed up for your first card in college just to score that free t-shirt. And admit a personal rookie misstep you might have made with said credit card.

Then gradually you can warm up to: “Have you ever looked up your credit score?”

If neither of you know, take a few minutes to get free estimates using mobile apps from Credit Karma, Credit Sesame or Credit.com.

What you really want to ask is: Do you have a lot of student loan debt?
Start with: How did you pay for college?

This is the question many dating couples probably want answered, as towering student loan debt is a sobering reality for many.

A conversation about how you afforded school—via scholarships, working and/or student loans—will help engage your partner. And along the way you may gain some insights into each other’s financial values or work ethic, too.

Once when you’ve gotten all these basics out of the way, treat yourselves to another margarita. Your first money talk out of the way! Now that’s a relationship milestone to be celebrated.

Farnoosh Torabi is a contributing editor at MONEY and the author of the book When She Makes More: 10 Rules for Breadwinning Women. More of her columns and videos for MONEY.com:

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