What’s the hardest thing to talk about in a relationship? You might assume it’s something intimate like sex, or perhaps navigating tricky family dynamics. But in our experience with clients, those issues often feel far more comfortable than diving into the topic of money.

Talking about money, whether in big or small ways, often triggers a surprising amount of anxiety and awkwardness. This can be especially true for successful, driven, and financially responsible individuals. Yet, it’s a conversation we can’t afford to ignore: a staggering 37% of divorces are attributed to financial problems.

Today, we’re going to make cents (pun intended!) of it all. We’ll explore who pays for what and when, what to do when you earn more than your partner, and when money truly matters—and when it doesn’t.

Should You Split the Check?

This is often the first financial hurdle in a new relationship. You might offer to split the bill or contribute, and in 99.82% of cases (a rough estimate!), he’ll likely decline.

A common concern we hear from successful clients is, “I don’t want to offer; my previous partners weren’t as financially secure, and I don’t want to fall into the same pattern.” It’s important not to make a current partner pay for the “sins of the past.” Besides, a split check isn’t necessarily a clear indicator of someone’s financial health or intentions.

Some argue that offering to split the bill shows you’re not looking for someone to take care of you, dispelling the notion that women are on the lookout for a free ride.

Our Take: Early on, let him pay. We generally default to the most common social script where the guy pays and takes the lead. That said, if he suggests splitting it, don’t completely write him off. Some men do this because they don’t want to be presumptuous or offensive. Most of the time, he’ll plan on paying the whole thing, so let him. A simple “Thank You” acknowledging your appreciation for the gesture is perfect.

From date three onwards, you can definitely offer to split, or even pick up the tip or dessert. Better yet, offer to treat him to a separate outing entirely! And here’s a crucial point: if he does let you pay for some part of the date, DON’T WRITE HIM OFF.

(Longer-Term) Who Pays for What?

As a relationship progresses, guys will often continue to take the lead financially, especially if they are well-off or have more money than you. However, regardless of who makes more, the key to keeping things “even” is to think in percentages, not dollar amounts.

For example, if you have twice as much money as him, you might roughly pay 2/3 and he pays 1/3. For a trip, he could cover the hotel, and you could get the flights, or you could plan a fun excursion or dinner. The goal is equitable contribution, not necessarily identical spending.

I Have More Money Than Him (and I Don’t Like It)

If you find yourself with more financial resources than your partner, it can feel a bit strange, perhaps even like it’s “not supposed to be this way.” You’ll want to think about how you want to handle this.

Consider this thought experiment: Should a billionaire automatically rule out a connection with someone simply because they aren’t in their tax bracket? Absolutely not! Why? Because you offer so much more than just finances or a number in a bank account. For relationships, a relative difference in income won’t be a problem unless you let it be.

Money doesn’t make someone a better listener, more supportive, caring, kind, or respectful. In fact, it can sometimes be the opposite.

Making the Minimum Threshold

It’s less about whether he makes more than you, and more about whether he meets a minimum threshold of financial health. This isn’t a set dollar amount, but rather an assessment of his basic financial well-being.

You want a partner who is financially healthy. Consider:

• His debt situation: (Though hard to know, what’s his credit score?)

• His expenses: (Does he have significant financial obligations, like multiple ex-wives or many children?)

• Does he waste money? (Is there a gambling problem or a tendency to spend frivolously?)

• Does he have a job? (And perhaps more importantly, does he like it? This is an underrated factor, often more important than the income itself.)

Ultimately, you need a “not broke” guy more than you need a wealthy guy.

Finances Aren’t Everything

If you’re only interested in a guy for his money, you’re likely setting yourself up for misery in the relationship. Money’s impact on happiness fades quickly, and there’s always more to desire.

Caring too much about a guy’s money isn’t fair because he’s looking for a partner who likes him for who he is—just as you would want the same. Women often worry that men only like them for their looks, and similarly, men worry that women only like them for the lifestyle they can provide. They might wonder, “Would she love me if I was poor?”

Instead of focusing on financial wealth, look for an emotional millionaire: someone who possesses confidence, emotional intelligence, handles stress well, is compassionate, a good listener, resilient, lives in the present, is mature, has self-respect, is authentic, respects others, is altruistic, and generous.

It’s Hard to Detect Financial Health

We often hear clients say, “I’m not going to waste my time dating this guy because he’s not at my same financial level.” But how can you really tell? “I can just tell,” they insist. No, you can’t.

There are many misconceptions:

• Wealth is obvious: It’s not always apparent from how someone dresses or acts.

• Wealth is flashy: Think of Warren Buffett—often humble in appearance. There are plenty of broke or indebted individuals with yachts and supercars.

• It’s not always the careers you think: The top five careers for millionaires are often engineers, accountants, teachers, management, and attorneys.

• It’s not even always about a high-paying job: Only 31% of millionaires averaged over $100K a year over the course of their careers.

Trying to “read the signs” or use stereotypes (like assuming all golfers are wealthy) can be misleading. Only 14% of golfers, for example, have a net worth over $1 million.

What’s His Approach to Money? (Spender or Saver/Investor)

In a relationship, you need balance. Research even suggests that this is one area where opposites can attract, as both people might aspire to have characteristics of the other (a spender knows they need to save, and a saver might want to be more carefree). Danger: Two spenders can lead to significant financial trouble.

• Saver: 94% of millionaires live on less than they make.

• Investor: The majority of millionaires earned money through long-term investing. Again, it won’t be obvious from the outside that he has money.

You can’t just ask, “So, what’s your net worth?” Instead, try a strategic, captivating question: “If you won $10 million in the lottery, how would you spend it?” This can reveal a lot about his financial mindset and priorities.

Should You Combine Accounts?

Research suggests that, early in relationships, combining finances can be beneficial. It fosters an “ours” mentality rather than “yours and mine.” Studies, even across all ages, show that pooling money encourages more open communication about finances and financial decisions. Couples who pool their resources tend to talk more about money.

One study found that “individuals who fully pool finances with their partner reported better financial communication quality and more frequent discussions about finances than individuals who partially pool finances or keep finances separate, even after controlling demographic differences and overall relationship satisfaction.” While power imbalances can harm financial communication, the key is to talk about it.

When you get together later in life, there are practical considerations:

• Amounts are bigger.

• The origin of money can be tricky (e.g., from a former spouse).

• Who the money is for later (e.g., kids, inheritance).

• You might still want to keep separate accounts for assets you worked hard for, or even separate homes.

When Is It OK to Give Guys Money?

NEVER EVER. At least, not until marriage.