The Money-Related Questions to Ask When Dating

In the realm of romance and relationships, one of the most important conversation topics for couples—money—is a source of discomfort. There is no recommended "moment" for when to talk about finances in a relationship. Instead, it should be approached frequently and commonly in conversations if your intent is to establish financial wellness in your relationship. Whether you're dating, engaged or married, a healthy discourse around finances starts with communication.

"How in the world did money get more intimate than sex?" opines Sallie Krawcheck, CEO and founder of Ellevest. "How did that happen? People go down the aisle and sleep together, but so many people go down the aisle without discussing finances."

But it isn't just about how much a person has in their bank account so much as it is about how both parties view money as a shared responsibility, says Mandy Len Catron, author of How to Fall in Love with Anyone: A Memoir in Essays. "Even if you hate thinking about money and your partner is a financial genius, make a point to share the work," she says. "How we spend shows what we value and it's hard to feel like you're on the same team when one person is making all the decisions. When talking about big decisions like opening a shared savings account or taking out a loan, it's great to explore your financial options—but do it together."

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When to Talk About Finances in a Relationship

So when should a couple talk about finances? While it's personal to you and your relationship, nearly a quarter of surveyed Americans believe bringing up the money talk is six months into a relationship, according to a study by Marcus by Goldman Sachs. Most financial experts assert, however, that couples shouldn't even wait that long and instead, discuss it throughout the relationship–even by dropping queues or prompts to learn more about the opposite party's money management skills.

Talking about money is foundational to a successful relationship because it establishes open lines of communication about what's important to each person. It's in your best interest to talk about finances sooner rather than later in a serious relationship.

How to Talk About Money When You're Dating

Since financial conversations aren't the most natural of topics to explore when dating, Krawcheck shares a few prompts that aren't specific to income levels or investments. In fact, these general questions to ask before dating or prompts to ask while dating could showcase how a person approaches traditional gender dynamics in relationships.

What are your thoughts on the gender pay gap?

Krawcheck says this prompt will help you learn more about the opposite party, beyond finances. It could point to how one party views the operations of a household. "We did an IG live the other day and one little tip I shared is, on those early dates, to bring up the gender pay gap," she says. "Introducing those concepts early on will show if you're getting traditional patriarchal responses–'There is no gender pay gap'–or if there is an openness to the topic."

Would you like me to get the check?

While there's much to unpack in the who-pays-what-on-dates discourse, this question is encouraged, says Krawcheck. "Women must always go for the check," she advises. "The last thing we want is something of the 1950s: an old-fashioned-he-pays-so-I-owe-him mindset."

"Even if he takes the check, the fact that you go for the check: you don't want to feel like you owe him," she adds. "You want to go into a place of equality and not what our mothers did: 'Three dates and he paid for it. Therefore, I have to sleep with him.'"

How should we split our dates, expenses and vacations?

An additional financial consideration to keep in mind while dating is levels of income. If one party, for example, makes significantly more, there are adjusted ways for couples to approach splitting bills. "So let's say you're dating before you get married," imagines Krawcheck. "And you say, 'Let's go through all of this and think through our budget: what does our joint budget look like? Do we have more coming in? I make $50K and you make $200K a year. What's the best way to split it? That way, you can work towards what is the right way to split the dates."

Why Financial Conversations Are Important When Dating

Additional questions to ask when dating, according to Krawcheck, include: "What kind of apartment or home can we afford together?" or "What is your student loan debt?" These are heavier-hitting questions that will impact your individual and overall financial wellness. Though it may seem daunting at first, here's why talking about finances while dating will bring value to your relationship.

"Money Dates" Help Couples Align Financially

But given that talking about money is never easy, how does a couple even begin to navigate the murky waters of finance while still keeping the romance alive? A study conducted by UBS in 2020 found that only one in four couples share financial decisions. However, they are the most confident about their future. Whereas, the same study found that couples who separate decisions about money argue the most about the same topic. A solve is having "money dates" once a month or quarter, when a couple schedules a night in (or out) to discuss their financial goals and current status.

"A great way to navigate this kind of stuff is to make time to sit down together and talk through those expectations before things get tense," says Len Catron. "For example, if money is a source of tension, make a regular financial date with your partner. It might sound unromantic, but it doesn't have to be painful. Order your favorite takeout and give yourselves an hour to talk finances. Instead of waiting for conflicts to arise, think of it as an opportunity to sit down and decide what you're working toward together. You're not making a budget, you're creating a shared vision for your future."

Tough Conversations Will Help Your Foundation

The payoff will be worth it in the end, she concludes. "The ideal relationship is thought to be one where your partner totally understands you from day one. They know what you want and how to make you happy, even you haven't figured those things out for yourself," she says. "This idea is at the heart of our fairytales and romantic comedies, but real relationships rarely work that way. I think the toughest conversations are those where you have to be honest with your partner about what you need or want."

"It's hard to make yourself vulnerable like that," she adds. "But practicing having those conversations can make them much easier over time."

–Joyce Chen contributed to this piece.