Dating is fun and exciting, but let’s face it, looking for a partner involves practical matters as well, such as thinking about financial compatibility and stability. It should not be as daunting as it sounds – treat it as exploring personality compatibility, or even chemistry.

Of course, financial questions should only be asked once you have had a fair series of dates.

The good thing about probing into financial compatibility is, these questions will eventually help you determine whether you should get serious with him or not. Ideally, make sure that you ask these questions under suitable circumstances.

Ensure the environment is pleasant, relaxed,  and that you both have a minimum amount of seriousness about having a romantic relationship with each other. There really is no correct answer that would dictate if you should accept or reject your date.

In fact, these questions help to gauge financial compatibility, as well as for you to determine reactions, both verbal and non-verbal reactions and understand the psychology behind his answers. This may help give you a preview of the relationship to come because, in the end, we do go on dates after all, in search of our life partners.

As Jefferson Bethke quoted, “Dating with no intent to marry is like going to the grocery store with no money. You either leave unhappy or take something that isn’t yours.”

Financial Questions To Ask Your Date #1 – Career Objectives?

Although you have the right, by all means, it might appear too awkward and straightforward if you ask a guy if he earns enough to your standards.  A more subtle approach would be to ask him about long-term career objectives.

In this way, he will not be taken aback and you would get a clearer grasp of his present and future financial capacities. Ask questions such as, what is his professional dream? A probe like this would make you look interested in his career, get to know about the job he currently occupies, and eventually assess his finances.

Financial Questions To Ask Your Date #2 – Prize Money?

Interestingly, hypothetical questions can do you good in wanting to understand your date from a financial perspective. You can ask him easy questions such as what he would do if he won a large sum of money in a lottery or competition.

Although it sounds playful, his answer would help you determine whether he is financially conscious. If he is wise about handling financial responsibilities, he will use his prize money productively. For instance, he might want to utilise it to pay off a debt or mortgage. If he is not financially clever, he will obviously want to splurge, such as for a luxurious holiday trip.

Financial Questions To Ask Your Date #3 – Saving and Spending Money Tactics?

Financial strategies can be vital to living a prosperous life. The best way to approach this topic is by asking him the tactics his parents worked out unitedly to manage or prevent any money problems. The answer to this should help you understand the strategies and support he is willing to give regarding money matters.

If he can recount some of these financial strategies, then you can expect him to be keen on using and developing these himself. This can put you at ease that he will be by your side strappingly through the financial crisis.

Financial Questions To Ask Your Date #4  – Dual Income Family?

This can be a very important question especially to women who value their career. By raising this topic, you will get a feel of whether your date expects his future life partner to continue her career or be a loving housewife. The easiest way to learn his future intentions is to ask him whether he grew up in a dual-income family.

Usually, people would prefer a set-up that they are accustomed to because of familiarity. If his parents both pursued their careers and provided for the family together, the chances are high that he does expect you to continue working. However, if his mother was a housewife, this situation can raise some concerns for you depending on your preferences.

Financial Questions To Ask Your Date #5 – Financial Risks?

Is your date a financial risk taker? This is an important issue because risk takers in finance are just that – risky. Winning becomes their main priority in life. Excessively high and frequent financial risk takings can lead to a huge financial loss.

Just ask your date casually, “If you see a marvellous sale on a branded long-term desired product for which you will be $6000 into debt, but will also get the chance to win one million dollars, would you purchase it?” A risk taker would obviously say yes, and in effect neglecting the amount of debt which he will acquire after the acquisition.

Financial Questions To Ask Your Date #6 –Present or Future?

There are two types of individuals, one who believes in enjoying the moment leaving future stability to fate, and the other who thinks of the future and builds savings steadily.  The former are people who spend money with no regards for the future.

You must ask yourself if you can live with such a person and trust him to support you with a financially stable life? The quickest way to know your date’s perspective as to whether he believes in immediate satisfaction or future reliability.

Financial Questions To Ask Your Date #7 –Money Regrets?

People make mistakes, and the ability to acknowledge and learn from them make us better people. The same goes for finances- ask your date whether he ever made a financial decision in the past that he regrets doing.

Preferably, he answers a yes. Humans make mistakes, but very few own up to it. Saying yes would mean that he has the courage to acknowledge and realise previous investments mistakes and learns from it. Thus, he can be depended on financially.

Read Investing 101: What’s Your Investment IQ?

Financial Questions To Ask Your Date #8 – Credit Score?

Women prefer men with high credit scores, but they also prefer men who speak honestly about it. You can gently raise this topic by mentioning your credit score. Say, “I checked my credit score, and it is greater than I expected. How is yours, honey?”

Financial Questions To Ask Your Date #9 –Shared or Personal Bank Accounts?

While personal bank accounts give you liberty and encourage self-sufficiency, shared bank accounts ensure the stability of your financial life together. Asking your date whether he thinks married couples should maintain personal or shared accounts can help you determine what kind of a spender or how financially aware he is.

Financial Questions To Ask Your Date #10 –Debts?

Debts are monsters to anyone’s financial life and security. It can be seen as one of the primary causes of rejected marriage proposals and divorces. It is important then to know about your date’s debts beforehand.

It is not a means to make him feel bad or worried, but an avenue for you both to logically discuss how to handle it together in the future.

Find out what happens When Women Earn More Than Men In a Marriage.

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Founder @ The New Savvy
Anna Haotanto is the Advisor (former CEO) of The New Savvy. She is currently the COO of ABZD Capital and the CMO of Gourmet Food Holdings, an investment firm focusing on opportunities in the global F&B industry. She is part of the founding committee of the Singapore FinTech Association and heads the Women In FinTech and Partnership Committee. Anna is the President of the Singapore Management University Women Alumni. Anna invests and sits on the board of a few startups. Anna is also part of the Singapore Chinese Chamber of Commerce & Industry Career Women’s Group executive committee. Anna’s story is featured on Millionaire Minds on Channel NewsAsia. She hosts TV shows and events, namely for Channel NewsAsia’s “The Millennial Investor” and “Challenge Tomorrow”, a FinTech documentary. Anna was awarded “Her Times Youth Award” at the Rising50 Women Empowerment Gala, organised by the Indonesian Embassy of Singapore. The award was presented by His Excellency Ngurah Swajaya. She was also awarded Founder of the Year for ASEAN Rice Bowl Startup Awards. She was also awarded the Women Empowerment Award by the Asian Business & Social Forum. Anna has been awarded LinkedIn Power Profiles for founders (2018, 2017), Tatler Gen T, The Peak’s Trailblazers under 40 and a nominee for the Women of The Future award by Aviva


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