4 Money Observations + Questions to Ask While Dating


There are many couples that debate over money or financial differences. For several people, currency is only a tangible item that serves one purpose which is to spend.

Would you give your date the boot if you found out they had $15,000 in credit card debt?

What if it was student loan debt?

How interested would you continue to be if you believed this person was throwing away their money on frivolous items, instead of squirreling it away for their future?

Those are very simple questions, which often require not so comfortable conversations. Money is a tool that is used to supply us with our basic needs, and our hearts desires. Without enough of it, our daily reality could be harsh and cold, depending on one’s personal beliefs about money. In today’s society, cash means different things to each of us. While some view it as a method to attain what they want, others view it more symbolically as a means of self-care and liberation.

As such, getting to the root of who we are dating, understanding their money mindset, and the why’s behind a mound of debt, or a sensible savings account, will help you to better understand if the two of you are compatible, based upon your non-negotiable items relative to finance. There are many questions that can be asked while you are dating that can keep you away from being labeled as controlling, a gold-digger, or looking for love or companionship based on financial security.

Time Capsule 

As you begin to venture back in time by discussing when you were a kid, conversations have a way of shifting to moments that we wish we had when we were younger, such as: “When I was a kid my parents worked a lot; therefore, I didn’t get to see much of them, OR “We didn’t have a lot of money when I was a kid.” These very profound statements will help you to understand if a person spends on a regular basis to fill a void. While this is not always a factual conclusion, it’s definitely a pathway to open financial dialogue.

Spending Habits 

If you have paid a visit to your date’s humble abode, chances are you are privy to gaining a peek into their style and spending habits. Are they dressed in the latest fashions, gleaming in top notch designer wear? Take that observation, and pair it with the furniture or lack of in their home. This moment is a great transition into light weight discussions on priority. The conversation could go a little like this: “Wow! This is nice where did you purchase it from? Do you shop there often?” Again, this is not an observation that leads to poor spending habits; however, it does allow you to  gain an understanding around the personal taste of who you are dating.

Forward Thinking 

Where do you see yourself in 3-5 years is indeed one of the most popular questions used throughout our entire nation. Most often used in interviews, or probed out of us by a mentor. This question answers a few things, how do you view success, and what are you looking for? This open ended query is ideal for a first date or even a fifth. If you believe that today is the day to begin taking charge of your finances, the response from your date is another red flag on the compatibility meter.


Obviously gratitude about all you have is very important. Therefore, being content in that place of thankfulness says a lot about the person we are dating. Are they after the next big thing? Disregards a penny on the street? Too embarrassed to use coupons? How focused are they on serving others? Take a step out of the box and request that your date be spent at a homeless shelter, or any volunteer focused event. Bridging passions together are a great way to incorporate both pleasure and purpose.

What are some methods that you use to measure finance compatibility?

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The Finance Bar is a personal finance suite helping women and couples achieve financial wellness through coaching, education, and an innovative learning hub on wheels. Creator Marsha Barnes is a Certified Financial Social Worker, Official FICO Brand Ambassador, and was named GOBankingRates’ Best Money Expert in the Net-Worth Category.

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