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Love & Money: The Most Expensive Decision You'll Ever Make

Who you choose to be with is the most important choice you'll ever make

What’s the biggest financial decision of your life? Investing in the next Nvidia? Timing the real estate market? Launching a side hustle?

Wrong. It’s who you choose as a partner.

Nothing—nothing—will shape your financial trajectory more than the person sleeping next to you. And since Valentine’s Day just passed, let’s talk about the thing that ruins more relationships than anything else: money.

  • 42% of adults admit to financial infidelity (hiding debt, spending, or entire bank accounts).

  • Money fights are the #1 cause of divorce.

  • Breaking up isn’t just emotionally draining—it’s a financial bloodbath.

So, in the spirit of preventing both heartbreak and bankruptcy, here are three uncomfortable (but necessary) money conversations you need to have with your partner.

(Apologies in advance if this email starts a fight. #Sorrynotsorry)

1. What’s the Financial Reality Here?

Before you plan a future together, you need to know what you’re working with. Not in a vague, “I think I have some savings” way, but in a cold, hard, numbers-on-the-table way.

At a minimum, you should know:

  • Income – Sets the foundation for budgeting and planning.

  • Debt – Student loans? Credit card debt? This impacts everything.

  • Savings – Reveals financial habits (or the lack thereof).

  • Major Expenses – How much is being spent, and on what?

  • Credit Score – Because one of you wants a house, and the other’s 580 score isn’t helping.

This isn’t about judgment—it’s about avoiding nasty surprises. The sooner you talk about it, the better.

SO WHAT?
If you don’t know where you’re starting from, you can’t plan a future. This conversation isn’t optional—it’s a financial prenup.

2. How Are You Splitting the Bills?

Once you know your financial reality, it’s time for logistics. Who pays for what? And how do you avoid the silent resentment that comes from one person always covering dinner?

Here are three common ways couples split expenses:

Method

Pros

Cons

Proportional Split (Each contributes based on income)

Feels fair if incomes are uneven

Can create resentment if one partner covers a lot more

50/50 Split (Shared expenses divided evenly)

Simple and easy

Can feel unfair if one earns significantly less

Joint + Separate Accounts (Shared bills, personal money stays separate)

Combines teamwork with independence

Needs clear boundaries and tracking

There’s no universal right answer—only what works for you two. But whatever you pick, automate it. The less friction, the better.

SO WHAT?
Money fights are rarely about money—they’re about fairness. Nail this down early, and you’ll save yourself a decade of passive-aggressive Venmo requests.

3. What’s the Plan?

Your partner should be a partner—not just someone who splits rent. Are you actually building toward the same future?

At a minimum, ask:

  • Short-Term Goals – What’s happening in the next 1–2 years? (Debt payoff? Big trip? Side hustle?)

  • Long-Term Dreams – Do you both want a house? Retire early? Move to another country?

  • Non-Negotiables – What are your financial deal-breakers? (Risky investments? Supporting family? “Just one more” startup idea?)

These aren’t the most romantic topics, but they matter. That’s why my girlfriend and I turn them into a date.

Every year, we rent a library room, bring an obscene amount of snacks, and map out our financial/life goals. Then we celebrate with a fancy dinner. Boring conversation? Sure. But the end result? A clear, aligned financial future.

Maybe don’t do this on Valentine’s Day—just bookmark this and circle back when you’re both in a good mood.

SO WHAT?
If you’re building a life together, you should have a shared blueprint. Otherwise, you’re just roommates with benefits.

Final Thought: The Cost of Avoidance

If you can’t talk about money with your partner, you have bigger problems than money. Financial alignment isn’t just about numbers—it’s about trust, teamwork, and long-term compatibility.

So have the conversations now. Rip off the Band-Aid. Future you will thank you.

NEXT STEPS:

  • Tonight: Start small—talk about one of these topics over dinner.

  • This week: Do a quick financial inventory (income, debt, savings).

  • This month: Set up an automatic expense-splitting system.

Because nothing kills romance faster than resentment over money.