Dating and Money: How to Talk About Finances Without Making It Awkward
When you’re dating, compatibility is deeper than just liking the same music or sharing a sense of humor.
It’s also about how you handle stress, make decisions, and ultimately, handle money.
Money isn’t exactly first-date material, but it does matter.
And if things are starting to get serious, avoiding the topic usually makes things harder down the road.
I work with couples all the time who are figuring out what it looks like to blend not just their lives, but their financial habits.
Some do it smoothly, others learn by trial and error. There’s no single right way to approach money in a relationship, but there are a few ways to make those conversations a lot less awkward (and a lot more productive).
What Financial Questions Are First-Date Worthy?
You probably don’t want to kick things off with, “Hey, how much do you make, and how much debt do you have?” 😬
There are ways to get a sense of someone’s relationship with money without going straight for the numbers.
One of the first times money naturally comes up is around who’s paying for the date.
That question doesn’t have to be awkward; it’s all about how you frame it.
If you’d like to cover the tab, make it clear up front:
“I’d like to take you out to dinner.”
Or, “Would you like to go to dinner with me, my treat?”
If you’re not sure how the other person prefers to handle it, ask directly (and casually):
“Can’t wait for dinner with you! Just wondering, do you usually like to split the check or have one of us grab it? I’m good either way.”
Beyond that, the first date isn’t the time for a deep dive into finances.
You can still learn a lot from lighter questions that reveal someone’s habits or priorities, like:
“Are you saving up for anything fun right now?”
“What’s your next trip or big splurge you’re excited about?”
Those small, natural conversations give you clues about how someone thinks about money — without making it feel like an interview.
When is it important to have money conversations in a relationship?
Any time you’re considering a bigger step in your relationship, it’s healthy to have a conversation about money.
There’s no single formula that works for every couple. You have to stay open and flexible to how those conversations unfold.
The key is to keep talking. The more often you do, the fewer surprises you’ll face down the road.
It’s also worth remembering that many “successful couples” I meet in my office don’t have the same income, spending habits, or savings goals. Most relationships naturally have a “saver” and a “spender.” The ones who make it work do so because they find common ground in their financial goals.
When should you discuss income and savings goals?
Early and often.
One of the easiest ways to start the conversation is by sharing your own situation first — talk about your income, savings habits, or goals. That openness makes it easier for your partner to share what they’re comfortable with, too.
As you discuss things like who pays for what, or how you each approach saving and spending, you’ll start to understand each other’s priorities.
If there’s a difference in income, it’s especially important to make sure your partner doesn’t feel judged or embarrassed about their situation. The goal is understanding, not comparison.
When is the ideal time to combine finances?
If combining finances is something that matters to you, it doesn’t have to happen all at once. Think of it as a gradual process.
For example, if you move in together, start by talking about how you’ll handle shared expenses. You might set up a joint account for rent, groceries, or utilities — something simple that helps you both contribute fairly.
As the relationship grows and marriage becomes part of the conversation, you can revisit what makes sense to combine. The right answer depends on your comfort level, your goals, and your ability to communicate openly.
How does a couple tackle debt together?
Debt is a math problem — but one with emotions involved. The most efficient solution on paper doesn’t always work in real life if one of you feels stressed or overwhelmed by what’s owed.
Working with a financial advisor can help you find the most effective plan to pay things off, but it’s just as important to find a plan that feels manageable.
When it comes to debt that existed before the relationship — student loans, credit cards, car payments — sometimes it makes sense for the person who brought the debt in to keep paying it off. In other cases, one partner might cover more shared expenses while the other focuses on paying down their balance.
There’s no one right answer here either. The key is communication and teamwork.
What are some financial dealbreakers or red flags to look out for?
If your partner is overly secretive about money, that’s a red flag.
Extreme habits can also be tough — if someone is either overly rigid or overly loose with spending, and it doesn’t align with how you handle money, that mismatch can cause real tension over time.
And if financial communication is always one-sided — meaning you’re the only one asking, planning, or being transparent — that’s a sign of imbalance that’s worth addressing early.
If you could go back in time, what’s the one piece of financial advice you’d give your single self?
Focus on putting yourself in the best financial position possible. The decisions you make early in your career set the foundation for everything that follows.
Not everyone starts from the same place — some people get a head start if their parents covered education costs, while others start out with student loans. The point isn’t comparison; it’s progress.
The sooner you take control of your finances, the more flexibility and freedom you’ll have to build the life you want — with or without a partner.
Ready to take the next step?
If you have follow-up questions or want to make sure you’re setting yourself up for success, reach out to the Aurora Financial Strategies team for a free conversation.
You can also email me directly at Billy@auroramgt.com.
Billy Cardwell, CFP®
Founder and President of Aurora Financial Strategies, a financial advisory firm based in Central Indiana.