3 Money questions for couples who just started dating (2024)

Money and relationships are often depicted to be like oil and water – they don’t mix. The problem is couples fail to ask the right questions and make observations regarding finances early on in dating because it’s taboo – it’s uncomfortable, vulnerable, private, forward and superficial. Yet having the talk is still important, so I came up with three money questions for couples to start asking when they are dating someone new.

Meanwhile, the more you shake the bottle the likely you end up exhausting yourselves to the point of irreversible devastation. And this simply shouldn’t be the case. Couples need to get more comfortable talking about finances sooner, especially when you consider that each and every person’s livelihood ultimately depends on that paper dollar. And by doing so, almost right off the bat you will be able to distinguish two things about someone:

1. They live to Work,
2. or they work to Live.

And I’d say that alone is pretty freaking important and impactful, right??? So let’s start taking the steps to remove that stigma and untouchable “POWER” behind money because at the end of the day it can either divide you or bring you closer.

You choose.

**This post is Part 1 of an upcoming 3-part series on helping individuals and couples get more comfortable discussing finances in dating and through the progression of their relationship. Sign up for TML newsletter to stay updated!

3 Money questions for couples who just started dating

My husband is a finance guru (he majored in finance) but he also has detective skills (no, really), so he knows his sh*t when it comes to asking the right questions to get certain answers. Obviously, I picked his brain and he gave me some insight on questions that couples who are dating should start unpacking early on. Bear in mind that some may not apply to you, but we collaborated on particular questions to help you get a better understanding of one another’s money “savviness”, financial goals, and spending lifestyle. The focus at this point, in the dating phase, is compatibility.

It’s also important to note that individual income is NOT the determining factor for financial compatibility. For instance, two very well-off individuals with extreme differences in spending habits or financial goals may not be financially compatible. And remember, inflexibility (the inability to compromise, bend or meet somewhere in the middle) is also incompatibility.

And while it’s no secret that asking someone on a first date, “What’s your relationship with money?” and others alike are not considered normal questions to ask someone you hardly know, let alone aren’t guaranteed long-term potential. When you’re dating, or on your few first dates with someone, you want to keep it light-hearted and fun, not interrogative. It’s understandable that there are certain questions deemed private and invasive, so the key is making observations and to ask leading questions to get the ball rolling and hopefully unpack those questions more in-depth if/when things progress.

Observational questions to ask yourself (and answer through context clues)

*These are strictly questions to keep in mind for yourself.

1. Do they respect money in the same or similar manner as you?
   • What are their spending habits? I.e., for example, what do they [obviously] like/prefer to spend their money on?
     • [Context clue]..If they tell you they enjoy going to upscale restaurants on the weekends, then they’re likely to choose spending their money eating out or on fine dining.
     • [Context clue]..If you notice they’re wearing high-end brand clothing, then they’re likely to choose spending their money on the “finer” goods and services.
   • Do they put too much or too little value on money compared to your views? I.e., Is their time consumed by money or do they spread themselves financially too thin?
     • [Context clue]..They make several remarks or spend a greater portion of the date bringing up the price of things. I.e., the happy hour specials, how expensive/cheap the menu is.
     • [Context clue]..They make several remarks or spend a greater portion of the date talking about the money they make/have, or the value in having [little/more] money. I.e., they refer to the dinner bill as “pennies” to them, or they talk about all the “luxuries” they have [a car, nice home, nice clothes, vacations] while struggling to pay their bills.
2. What are the steps they’re taking toward becoming/being financially established?
   • Are they financially responsible? I.e., They can provide and take care of their basic financial responsibilities (food, bills, gas, etc.).
     • [Context clue]..They comment about how they like to cook, or make remarks about their current living situation/financial status.
   • Are they spending money they don’t have? I.e., They have the latest and greatest “amenities”, yet struggle to make ends meet.
     • [Context clue]..Pulls up in a Mercedes though his credit cards get declined trying to pay for a date.
   • Do they have financial goals? I.e., Getting a degree/certification, establishing a budget, transitioning to live solo, etc.
     • [Context clue]..They tell you they’re working on getting their Masters or a promotion at work.
3. What are their long-term financial goals?
   • Do they have or are they paying down debt? I.e., student loans, mortgage, car payment, credit card, etc.
     • [Context clue]..They acknowledge their currently working more over-time to help pay off student loans.
   • Do they have savings or are they saving up for something? I.e., to buy a house, a newer car, retirement, etc.
     • [Context clue]..They’re currently living with their parents in order to save a year’s worth of money for a down payment on a house.
   • Do they invest? I.e., stocks, 401K, rental properties, etc.
     • [Context clue]..They tell you about a new job they’re excited about because it has better benefits with a retirement plan compared to their old job.

Leading questions to help you make the above observations

*These are first-date-worthy questions to be discussed and expanded on in the dating process (~0-3 months).

1. [Do they respect money in the same or similar manner as you?]
   • What to ask: “What do you like to do in your free time?“
     • [Follow-up].. “What does a normal weekend look like for you?“
     • [Follow-up]..”What are your hobbies/guilty pleasures?“
   • What to ask: “If you won $5,000 from a scratch off, what would you do with it?” **The key is you want this number to be “realistic”
   • What to ask: “Would you rather live a luxurious lifestyle with little freetime, or a modest lifestyle with more freetime?”
     • [Follow-up]..”What would you spend your time doing/money on?“
2. [What are the steps they’re taking toward becoming/being financially established?]
   • What to ask: “Do you enjoy your job? Is this your career path?“
   • What to ask: “Do you like where you live?“
3. [What are their long-term financial goals?]
   • What to ask: “Do you consider yourself a planner, or the ‘go where the wind blows’ type?“
   • What to ask: “Where do you see yourself in […] years?“
   • What to ask: “Are you putting down your roots?“

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