There comes a point in every relationship when you have to broach the uncomfortable subject of money. Splitting dinners, splitting bills, merging bank accounts, signing prenups — all touchy, but necessary, conversations couples need to have. Still, most couples tend to avoid the subject of finances altogether.
“About 50 percent of married and cohabiting relationships won’t talk about money,” Jason Tartick, host of the popular business podcast Trading Secrets and former contestant on The Bachelorette, tells InsideHook. “They feel very uncomfortable talking about money, but the problem is that we’re not having that conversation.”
“Money is more than just dollars and cents — it’s highly emotional, with our life experiences shaping how we feel about money,” adds Dr. Traci Williams, a certified financial therapist. “In fact, a recent survey conducted by Chime found that 39% of men say they feel pressure to appear more financially stable than they actually are. That pressure can make people defensive or avoidant. Normalizing money talks early helps take the stigma out and shows that it’s about partnership, not judgment.”
Maybe there’s a financial conundrum you want to bring up to your partner, but you’re dragging your feet — or you just want to know the dating and money fundamentals, like does the man always have to pay on the first date?
Lucky for you, I decided to pose all of those awkward questions to the experts — so you don’t have to.
With insight from Dr. Williams and Tartick, here’s everything you wanted to know about finances and dating, but were too scared to ask.
Should a man always pay on the first date?
Jason Tartick: I’m a traditionalist in that fact. Yes, personally I would. But I will say there’s no cookie-cutter answer. The best way to approach it if you’re unsure, uncertain or not willing, is to have the conversation before. It’s such a taboo thing to talk or ask about, but in dating in general, it should be built on connection and not consumption. And so you can easily have those conversations to avoid that awkwardness.
Am I allowed to ask my partner to split the bill?
JT: I feel like that might be even harder than paying for the first date. The best solution is a teeter-totter approach, which is based on how much you earn, that’s how much you spend in the relationship as a percentage of. So it should be equitable.
TW: Keep it light and collaborative. Chime’s survey found 23% of Gen Z prefer splitting the bill, and 28% think whoever plans the date should cover it — proof that many people are open to different approaches. You can say something like, “I’ve really enjoyed treating us, but I’d love it if we could start balancing things more evenly. What feels fair to you?” Framing it as teamwork sets the tone for fairness, not conflict.
Should couples combine bank accounts? Or keep it separate?
TW: There’s no one-size-fits-all. Many couples find a “yours, mine and ours” approach works best: keep individual accounts for personal spending, but also create a shared account for bills and joint goals. That way, you maintain independence while still building trust and teamwork. Others determine that separate accounts can work best. What matters is that you both openly talk through this decision and each person agrees that the arrangement is fair.
I’m worried about telling my partner how much debt I’m in. Do you think I should disclose this, and how should I go about it?
JT: Let’s say you have debt or you have credit card debt. That’s not the issue. The issue is that no one’s actually talking about it. Or the issue is that you bring it up and you’re met with judgment, weaponization, shame or blame. Imagine you go to the doctor’s office and you’re not willing to talk about what’s actually wrong with you. How can you solve it? All of us have money issues to some capacity, but if you’re not willing to talk about it, you can’t solve it. We need to stop meeting vulnerability with judgment, and we have to stop lying about it.
TW: Yes — honesty matters. Debt isn’t just financial; it’s emotional, too. The key is timing and framing. Wait until the relationship feels serious, then share in a way that shows you’re taking ownership: “I have debt, but I’m working on a plan to manage it.” Framing it as something you’re actively tackling makes it less about the burden and more about your commitment to growth.
Is there anything you can keep private regarding finances with your partner, or should you be 100% transparent?
TW: Transparency builds trust, but that doesn’t mean you need to disclose every coffee purchase. What matters is being open about the big stuff — debts, goals, habits and how you want to manage money together. It’s okay to have personal spending money in a separate account as long as both partners agree on the system. Some couples agree to a threshold amount they can spend without telling the other, say $100. This allows you to have agency over your money and maintain openness in your relationship.
JT: I like the idea of independent bank accounts. I don’t think every single thing should be micromanaged, but I also think material purchases that could be a big swing for the family should be discussed. The biggest thing is, if you’re keeping it from someone, why?
Should couples always get a prenup?
TW: A prenup isn’t just for the wealthy — it’s a financial plan. Think of it like insurance: you hope you never need it, but it protects both people if things don’t work out. At minimum, couples should have transparent conversations about money, assets and expectations before marriage, whether or not they choose to formalize it with a prenup.
JT: Big fan of prenups, and with a prenup, you can customize that based on your financial situation.
Are there financial red flags I should look out for?
TW: Yes — and they often show up early. Consistently overspending, hiding purchases, refusing to talk about money or carrying debt without a plan are all red flags. In dating, watch out for someone “flexing” financially in ways that don’t match their lifestyle. 33% of singles say living beyond your means is a dealbreaker, so trust your gut if something feels off.
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