There’s nothing like the thrill of a new romantic connection. The butterflies when their name lights up your phone. The late-night conversations that stretch way past bedtime. Thoughts about the future. In those early weeks, everything feels shiny and full of possibility. But eventually reality shows up. Between the sparks and the sweet talk, there’s the question of how you actually live—what you value, what you prioritize, and yes, even how you spend. As much as we hate to admit it, how we treat our finances can be just as important to compatibility as chemistry.
I learned that valuable lesson in the early stages of my last long-distance relationship. Our first big fight was about spending $300 on a plane ticket so that we could spend a few days together. I thought booking the flight was a no-brainer. He wanted to wait. “We respect money differently,” he told me, and it hurt. I felt judged. To me, it sounded like he thought I was being irresponsible with my funds. Even worse, what I heard was that I wasn’t worth the cost. The fight cracked open deeper conversations about how our upbringings shaped our money habits and what money meant to us individually. We compromised, but the truth was clear: money wasn’t just about dollars, it was about values. If we hadn’t had that clash, we might never have uncovered just how different those values were.
So how do you bring money into the conversation early without killing the vibe? I spoke to four experts who specialize in love and money: financial educator Ross Mac, known for Maconomics, licensed therapist Beverley Andre, life coach Shavon Terrell-Camper, and relationship coach Edith Yvonne. Their advice proves that talking about finances doesn’t have to be verboten; it can actually be a way to deepen intimacy.
Understand Their ‘Money Story’
“Money should no longer be taboo,” Mac says. “If I’ve got debt and we get married, we both inherit that debt. Habits don’t disappear at the altar.”
The numbers back him up. More than 60% of Americans live paycheck to paycheck. Nearly half can’t cover a $1,000 emergency. And finances consistently rank among the top two causes of divorce—right alongside infidelity.
“I don’t think the first question is, ‘How much do you make?’” Mac says. “Start with directional questions: Do you invest? Do you have a retirement account? Ever thought about owning a home? That tells you whether someone’s moving in a positive direction.”
Terrell-Camper calls this exploring someone’s “money story.” “Numbers give you outcomes,” she explains. “But you need to know how they got there. Did their parents give them a boost? Did they grind it out? If you only look at the score, you don’t know the mindset that produced it.”
Each expert emphasized that values come before numbers. Instead of leading with questions about salary or credit scores, start by paying attention to how someone thinks about money.
“Money highlights your values,” Andre explains. “It shows the kind of life you’re trying to live. The earlier you start these conversations, the earlier you see if your visions align.”
Terrell-Camper adds, “A person’s relationship with money can tell you so much about who they are. Part of dating is finding matches. Are we a money match?”
Edith Yvonne agrees. “Values are what make or break relationships,” she says. “The more congruent you are in values, the more likely you can sustain the relationship. Numbers and specifics can come later, once you’re building a life together.”
Try leading with the following queries:
- “How did your family talk about money when you were growing up?”
- “What did your parents teach you about bills, debt, or saving?”
- “How do you decide when to splurge versus when to save?”
These questions surface not just financial habits, but also cultural and family histories that shape them. Because we’re all raised differently, it’s important to understand that we all have sensitivities around what we were (or weren’t) taught about managing our finances. Recognizing cultural context helps partners replace judgment with empathy.
“DNA isn’t the only thing passed down,” Terrell-Camper states. “We inherit stories—about money, emotions, relationships—from our families and communities. If you grew up where money talk was taboo, even if you want to be open, you may not have the skills. Money conversations are a skill. And not everyone arrives in adulthood with mature money skills.”
Don’t Talk Finances on Day 1
So, when is the “right” time to talk finances with your prospect? There aren’t hard and fast rules, but our experts suggest taking some time to get to know your new connection before approaching them about their investments—or lack thereof.
“People put too much at stake on a first date,” Andre says. “Those should be low risk. Give yourself time to know the fullness of a person before ruling them out.”
At the same time, Yvonne believes having in-depth money talks is crucial before taking any big steps with a relationship. “Once you’ve identified this is someone you might want to do life with, have the conversation,” she says. “If you can’t, you’re not ready for marriage.”
Terrell-Camper suggests starting indirectly: “Instead of asking someone their salary, lead with curiosity. Say, ‘I’m focused on my finances this season—paying down a card and investing. Is that something you’re comfortable talking about?’ You share first, then invite them to share.”
The truth is, most people you date will have debt. The difference is whether they’re willing to do the work to improve their financial outlook, or if they’re continuing the behavior that put them in debt in the first place.
“Stagnation is the red flag,” Ross Mac says. “If someone knows their shortcomings and is working on a plan, that’s different from someone standing still.”
Terrell-Camper recommends stress-testing. “Ask, ‘What do you do under pressure?’ If the answer is shop, gamble, or drink, that’s telling. Pressure brings out our money defaults.”
It’s important to discover the why behind any red flags. “Debt isn’t all the same,” Yvonne notes. “A woman who maxed out credit cards to escape abuse? That’s survival debt. Someone racking up charges to impress strangers? That’s self-esteem debt. The why tells you whether you can build with them.”
With that said, Andre warns against shaming an individual once you know their fiscal reality. “Judging someone for their financial situation is a huge no.” She emphasizes that curiosity is key. “It’s okay to say, ‘Hey, this is concerning to me. What’s your plan? What have you tried? Are you open to help?’ If the answers involve denial, you have your information. You can leave without judging.”
Try a ‘Willingness-to-Learn’ Test
“If they’ll read a book, attend a workshop, or make adjustments, that’s a healthy sign,” Terrell-Camper says of trying a “willingness-to-learn test” to determine if certain money habits can change. “Sometimes we don’t do better because we don’t know better.”
Mac suggests practicing discipline with a shared goal: “When my wife and I were dating, we opened a separate account for a down payment. Even if you each put $50 or $100 aside, the point is showing discipline together. Relationships are built on sacrifice. If someone can’t sacrifice for their financial goals, that might show they won’t sacrifice in the relationship either.”
Andre also advises the couples she works with to have monthly or bi-weekly financial check-ins, alongside relationship check-ins. “If one partner needs to see savings grow and the other needs to live in the now, create both accounts: retirement, savings, and fun money. Both/and, not either/or.”
Yvonne also emphasizes the importance of teamwork for couples who aren’t necessarily on the same financial footing. “Who cares if you out-earn him? In every relationship, someone makes more. The question is: what are we building together? Money should never be used as a weapon.”
How to Ask the Right Questions
Need some help starting the conversation? Try these expert-approved phrases:
- Early dating: “I’ve been thinking about my financial goals lately—what about you?”
- Two months in: “I want to buy a car in the next year. What would you do in my shoes?”
- Exclusive: “What’s your philosophy—save first, or live first?”
- Moving in: “Let’s talk about how we’ll split expenses and what each of us values most.”
- Engagement: “Here’s my student loan balance. What debts or accounts should we lay on the table?”
A pro tip from Andre is to always share your own example first. “Whatever you’re asking, you should be able to answer too,” she says:
- Ask yourself first: What’s my money story? What did I see growing up about bills, saving, or debt?
- Early dating values check: Slip in, “What would you do if you won $5,000 tomorrow?” The answer reveals priorities.
- Observe, don’t just ask: Notice spending habits, reactions to unexpected expenses, or how someone talks about work stress and money.
- Monthly check-in (for serious relationships): Combine a “state of the union” chat with a “state of our finances.”
The next time you’re tempted to avoid the subject of finances, remember that talking about money early is really talking about values, trust, and the kind of love life you want to build. The real flex isn’t avoiding the topic—it’s having a relationship where you can comfortably share your numbers and your needs, then create a future that honors both.