Financial Foreplay: 20 Money Questions to Safely Ask a Date

How to start money conversations and find your financial soulmate. A must-read before your next date.

In a few short paragraphs, I will show you how to softly lead into the money conversation and learn your partner’s financial IQ quickly before committing without your partner even noticing they started to talk about money.

Should You Discuss Money in a Relationship

Money and sex regularly rank as the most common reasons couples fight. Research from LearnVest’s Money Habits and Confessions Survey, conducted by Wakefield Research, concluded that financial issues are more than twice as likely as sex to cause tension in a relationship.

Finances can even end a romance, with nearly one in four Americans saying they broke up with a significant other over money issues. Most Americans say they would prefer to be single rather than cope with a financially irresponsible partner. How would you like to head off one of the biggest relationship killers right from the first date? If your time is your most precious resource don’t waste it on those that are not worthy of your time. OK with all that in mind, when is the right time to talk about money?

Financial Foreplay: When is the Right Time to Talk Money?

You want to know how responsible a potential partner is with money but don’t know a smooth way to lead into the topic? Here is a quick article on how to broach the taboo topic of booty. No, I am not talking about your dates perfect posterior, stay focused. I am talking about broaching the conversation about booty, loot, cha-ching, greenbacks, money that is.

One question that I get a lot, is when is it safe to finally talk about money. The first Date? First month? First year?… The answer might surprise you.

The correct answer is immediately. Think about it! You are instantly assessing the other dimensions of a person’s compatibility from the second you see them and begin talking to them. Everything from how attractive they are to how many kids they want to one day have. You are measuring them up whether you are conscious of it or not.

Assess the Attraction Level

Using Lots of F-words

Now I don’t recommend trying to impress your date with “locker talk” or a limited linguistic vocabulary.

These are the F-words I recommend to use on a first date. You want to assess if there is natural chemistry and mutual compatibility across the different dimensions of their personality. If your conversation centers around these topics you will get a good idea of their personality and your level of connection with them.

• Fine
• Faith
• Family
• Friends
• Fitness
• Finances
  
  
  

Fine

Are they fine, that is, are they attractive? The reason I am starting with this one is because it can be instantaneously assessed whether or not you are attracted to someone. Often without even needing words. Whether or not that is a conscious choice or an involuntary neurological or chemical response is up for debate in intellectual circles but the results remain. Looks or physical attraction is one of the quickest ways to determine if there is a high or low level of attraction to someone. So are they hot or not.

I was out downtown recently and a woman walked in the door with a smile so genuine and so big I had to know more about her. Why was she so happy? What was going on in her life that cultivated such a big smile? What about her attitude allowed her to enjoy her evening so much? she was so interesting that I spent the rest of the night talking to her and ignoring the other girls in the bar. It was not her general attractiveness that drew me to her, I could just sense that something was extraordinary about her. My point is that sometimes attraction is more than just good looks.

Faith

Most People either care about this quality deeply or don’t care much at all. Either way, you rarely connect with somebody that’s on the opposite end of the spectrum than your personal beliefs. Whether this is the most important quality to you or the least important, it is unlikely that you can connect with somebody that’s not on the same level of faith as you.

Family

A date, if it goes well, naturally evolves into a relationship. A relationship, if it goes well, can evolve into marriage. Marriage is a union of a man and a woman into a family. Therefore how a suitor treats his or her family is often an indicator of how they will treat you as a relationship evolves. How strong or weak a person’s family connections greatly shape and influence their development through the course of life. These relationships are the most important contributions to a person’s fundamental development of happiness, confidence, and capacity to demonstrate love.

Friends

Friendships are often a shadow of family relationships. I find the most highly motivated and successful people often have strong, close, deep, and meaningful friendships with people that they can count on and with the people to count on them. The depth of someone’s relationships is often an indicator of their skills in communication. The better communicator they are the more likely you will be able to work through life’s problems with others. You know what they say “your network is your net worth.”

Fitness

If you are a natural-born runner and your date is a natural-born gamer you are inherently going to share less time and activities of interest with them because of that disparity. Seek a good match in your energy level. Personally, I am a very active and athletic guy. Activities, sports, and exercise take up a large portion of my daily life, hobbies, and interests. Because I lean so far on the active end of the spectrum I find it very difficult for me to connect with people that are more sedentary or less motivated to move a lot in their daily rituals.

Finances

Finally, we get to Finance. If you haven’t noticed by my writing I get pretty jazzed about the subject of finances! I simply would not mesh well with someone who is financially uneducated or financially disconcerted. Not only is it a point of interest to me but also as a very important parameter of leadership for my family.

A healthy and successful life requires a healthy and successful financial life. I need someone who will make a good team player for team Refined. Someone who will lead by an example of frugality and wise money management to help build the Family Freedom Fund. I need someone who will honor and uplift my decisions and leadership for the financial success of my family.

More Meaningful Conversation

If your conversation revolves around these F-words you’re more likely to effectively assess whether or not this person can offer a natural connection and a mutually compatible relationship with you. So, unless you are just out for a free meal (shame on you if you are) light a fire under the conversation by talking about more meaningful subjects than the sports game, weather, or other superficial fraternizing that I hear from people on dates.

Who knows, maybe you will actually land a date that is five out of five of the S-words: Sane, Single, Sexy, Sweet, and Spiritual. Although, I hear scoring 5:5 is harder than unicorn hunting.

How to Start the Money Conversation

Now that you have permission to talk about money, how do you go about it like the suave seducer you are in other areas? Talking about money with your partner can bring you closer together because you’ll communicate honestly as you determine your compatibility. Later down the road, healthy money conversations can even strengthen your relationship as a committed couple. Starting with a foundation of an open line of health communication on finances can eliminate one of the leading reasons for stress and break up later down the road.

I’ve curated this list which is best suited to the early dating phase of a relationship. The intent is to indirectly ask them about money so they don’t feel any blame or shame about their money choices or financial literacy level. These questions indirectly reveal what your date’s relationship is like with money, often without them even realizing it.

To Firm it Up

If you further along In your relationship you can drill a little deeper or be more direct with their personal situations or experiences. Point is you’ll have to read and gently guide the conversation based on their comfort level in their responses.

To Tone it Down

If your date responds defensively you can always spin of the question by answering briefly for yourself in a light playful way and deliver your response with a warm friendly smile then ask them a question about something else they enjoy. Then later you can revisit the subject with a softer or less direct question. Take warring though if they get defensive easily about this subject it may be an indicator of bad money habits or embarrassment about their financial situation. Often, people who have been successful with their finances like to talk about it. And those that have been unsuccessful like to hide or avoid the topic.

What to Avoid

Don’t just plow into a litany of all 20 money questions as you consecutively march down the bullet point list below. Your on a date, not an interview. If you going to be that guy/gal you might as well just ask them their net worth on the first date and laugh loudly when they answer. No, no, no you are far too refined for that.

What to Aim for

Here are some helpful pointers to initiate safe conversation about money without raising the defensive tensions that surround the taboo topic. Remember you want to raise the topic without raising the tension. Be playful with these questions and don’t be shy to go first with a little candid venerability to set a comfortable honest tone. The goal is sharing life experiences to know where they are at in their life long financial journey.

Sprinkle a few of these in each date you go on. Pick a natural transition in the conversation when you’re both relaxed and can share uninterrupted. If you are talking about family life growing up, pull out one of the questions about their family such as “How did your parents talk about money as you were growing up?”

If they are talking about their dream job ask them “What are your money dreams …with the income from that job?

The point is to be playful be warm friendly and inviting. Cultivate a safe atmosphere. My friend Victor always jokes with his dates that he will pick them up in the “Honda of fiscal responsibility.” Not only does this indicate the vehicle that she should be looking for but it communicates that he is responsible with his money and values the content of character over trying to impress women with his choice of car.

This has the benefit of naturally weeding out the women who are looking for a sugar daddy. Note the irony that his fiscal responsibility would actually provide more “sugar” for a lady over the course of a relationship. But hey ¯\_(ツ)_/¯ my job is not to reason with the unreasonable.

Financial Foreplay: 20 Money Questions to Safely Ask a Date

With no further ado, here are a few questions to ask to get the gears turning and get a sense of how your date feels about and act with money. I got this first one from my friend Seonwoo Lee at FinCon a few years ago and it has been a great litmus test for a date’s personal relationship with money. Read this list and keep them in mind as you go bravely go forth into the dating scene. Remember the goal is to learn their financial education level and decision skills about money without blame or shame.

• If you were given 1 million dollars today, what would you do with it?
• What is one expensive food you really love? What’s a cheap guilty pleasure?
• If you could be famous or secretly wealthy but had to be totally discreet what would you choose?
• If you had all the money you needed to retire today, what would you do tomorrow?
• What splurge would you never give up?
• Who or what was your biggest financial influence?
• Did your parents demonstrate a good example or a bad example of how to handle money?
• At 20, where did you think you would be at 30? How close or far are you from that person?
• Do you have any financial goals?
• Have you ever had an “ah-ha” moment where you felt “I am an adult now?” If so, what was it that made you feel that way?
• Would you rather A) Drive a 10-year-old Honda Civic for the rest of your life, if by doing so you would double your income every year or B) stay at your current income but get to drive a Ferrari and trade it in every year for the newest year model?
• What was one of your biggest bucket list items? What are your short-term goals?
• Did your parents talk about the family’s finances when you were growing up and what were some of the lessons you learned?
• Do you consider yourself good at budgeting?
• Did both of your parents work? How did they handle income?
• If you had to choose between working a job you hated for $400,000 a year and a job you loved at $40,000 a year, what would you choose and why?
• How old were you when your parents stopped taking care of you financially?
• Do you have any financial regrets?
• Are you a natural saver or spender?
• What are your money dreams?
• What do you think your life will look like in 10 years?
  
  

That’s it! So now you have permission, tactics, and empowerment. Go forth and broach the taboo topic and when you do let me know how it went. As luck would have it… I have prepared this handy comment section for you below. Happy unicorn hunting.

Keep the FIRE burning my friends.

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This has been a fun article if there is any interest in more dollar vs dating, finance vs romance articles I would love to write more on this subject. If you want to hear more about how to handle dollars and dating hit me up let me know.

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Oh, and save yourself the email. I know that there are 21 questions. I thought of one more. BTW, if you counted just to make sure there were 20 you really need to get off your screen and get out on a date.