Susan Piver's book, The Hard Questions: 100 Essential Questions to Ask Before You Say “I Do,” has helped thousands of couples connect — or realize they should split.
We asked members of Millionaire Single Moms, our Facebook group, to share what questions they would ask before remarriage — plus what questions they would ask a boyfriend or girlfriend now.
What are your goals in 2 years, 5 years, etc.
A shared vision for a life together is important.
What is your vision of married life?
Do you do everything together, or does each partner have their independence and unique hobbies and friends? Is alone time important?
Do you give an engagement ring for a second marriage?
Do you want children and how many?
Deal breakers, here.
How will household duties be divided?
A dirty dish in the sink has been known to be the straw that broke
many a marraige. That said, frank, loving discussions can help set expectations.
How do you track your expenses (not, do you track your expenses)?
Learn more about how to set up a budget in this post.
How much debt do you have?
- Does he or she know the answer?
- Are you comfortable with the answer?
What are your interest rates on your debt?
Shows the level of interest in personal finance.
What is your credit score?
See above. Credit in a relationship is a big deal, and affects your ability to reach goals like buying a home, car or wedding.
How to improve and protect your credit score— and get your credit report for free.
What are your values around money?
This question may be hard for some people to articulate, so be patient with the answer. A similar question with the same answers may be: What are your values?
How important was it to your parents to manage their money?
Childhood models for money management are a good indicator of a person's adult habits, but you can't judge a person by their parents.
How much life insurance do you have?
Careful, you might come off as a murderer/gold-digger, but still a good Q.
How to find affordable life insurance
Are you a Gofund me person?
Answer may showcase empathy, or stupidity.
Talk to me about some of your savings goals?
This question is less about money, and more about ambition, drive, dicipline.
How close are you to hitting your goal?
Success is sexy! Big talk with no action is a big turn-off.
Did you have any setbacks? If so, how did you overcome that?
Resilience = important and attractive. Also, it is interesting to note whether a person has the humility to admit defeat, struggle or hardship.
Are fancy things important, or are you okay living frugally?
A common sensibility about personal finance, saving and spending is a big deal in a long-term relationship.
Where (geographically) do you want to live?
Close to friends and family? Does one partner need to be close to a certain location for a job? City or rural, mountains or beach?
How do you envision retirement?
If you both envision lots of downtime during retirement that can bring you together. Or, if you both plan to be very active with work and service activities, that can bond, too. Or, you may agree to live different lifestyles in your retirement years.
What makes you feel loved and supported (knowing these will change over time)?
Love languages are a big one here. One of the seminal relationship books of all time: The 5 Love Languages: The Secret to Love That Lasts.
Can you walk me through the past few years of your life and provide more detail around how your circumstances or actions align with these dreams?
Recent history is the biggest indicator of future outcomes. Getting over divorce or breakup, being a better parent, financial setbacks like bankruptcy are all part of a human life. How you get through them and overcome them show who you are.
What have you accomplished that is getting you closer to your goals?
If personal growth is important to you, you likely want to be with someone who is also actively working to improve themselves.
What are your strengths (other than selling me what you think I want to hear)?
Self-awareness is important — and sexy.
What setbacks have you overcome?
An answer to this question can display humility, growth and give the question asker insight into what shaped this potential partner.
What are your values?
Not only is the answer to this question important, but the ability to answer it with clarity also shows that the person has thought about who they are and what is important to them.
How do you define yourself?
Again, a way to express who you are shows maturity, and what matters to you.
How important is reading to you?
Intellectual curiosity may be a deal-breaker.
Proactive/Reactive?
The answer may be “a little of both” but this is a good, provoking conversation that can help you both learn about one another.
What does it mean to you to be a good parent?
Parenting styles can make or break a relationship, especially if the kids are still at home.
How do you co-parent?
If you have a blended family, your step-children's mother or father will be a big part of your life — and the relationship your husband or wife has with them today makes all the difference in how happy your home is.
What is co-parenting? Find out with all the resources you need
How do you discipline (if at all)?
Different parenting styles can make or break a relationship.
How do you define your role as a support to your pregnant spouse?
This question may come off as loaded with baggage from a previous relationship or old wound — which is OK. It's on your mind and important to you.
How do you plan to support me, should we agree to have more children? Emotionally, financially, physically, mentally?
And of course you will be prepared to answer the same question for him.
What do you know about mental health? How would you handle things if I was struggling with mine and how do you handle things when you’re struggling with yours?
This is a bold, honest question that may make a potential husband or wife nervous — or grateful.
How do you feel about cosleeping with your child?
This has broken up many a relationship. Some parents love the snuggle all night, others resent the cramped space.
How do you want to spiritually nurture our child, especially since we were of different religious backgrounds?
Different religions is a common reason for breakup and divorce. Front-loading these discussions can be helpful.
How will we manage a child with special needs if that arises?
Hard to know unless you live through it, but worthwhile conversation to understand a boyfriend or girlfriend's inner workings.
How do you picture work/home life balance after a child?
The answer may be a combination of goals, past experience with a previous partner, reflection on childhood experiences. Also, if your partner has not considered this topic, that is telling, too.
Will one of us stay home or will we use childcare?
If stay-at-home parenting is your goal, better get this one out there now.
How do you communicate when triggered?How do you deal with major stress?
Sometimes, you just have to live through it with the other person to know — so this is a question for you to keep an eye out for the answer through behavior, rather than an explicit verbal response.
Even if the person's ways of stress relief are hard for you to comprehend, if they can be honest and self-aware in their answer, that shows maturity.
Do you have a spiritual life? Are you religous?
Some couples of different religions are compatible because they are both equally passionate — or ambivilant — about their faith. Other times, a difference in religous practice drives boyfriends and girlfirends, husbands and wives apart. Or, if one person is committed to deeply exploring their spiritual life and the other is not, that can be a deal-breaker.
How would we would make decisions regarding major life changes?
Winner-takes-all? Compromise and negotiation?
What issues from childhood are you still battling with?
Can we all really answer that 100%? Isn't it a lifelong struggle? Interesting conversation, though.
What addictions run in your family and how have you dealt with it?
Addictions, including to alcohol, illegal and prescription drugs, sex, gambling, porn, shopping, social media and work. A frank talk about family history, recovery, co-dependence and related topics will open deep droves of information and discussion — if both aparties are open to discussion.
Do you plan to raise your children the way your parents raised you — or are you flexible and open to something different?
The root of this question is really about whether the other person is self-reflective and growth-oriented.
How important is exercise to you? How important is it for your children to exercise?
If one person is not fit, and the other is … well ….
Do you believe in eating healthy?
Big lifestyle differences can break a relationship — while similar, healthy eating and fitness can bring you closer together and
Will you still love me if I’m fat?
More questions to ask your girlfriend or boyfriend
A few years ago, an essayist for the New York Times' Modern love column wrote about using the 36 Love Questions that pschologist Arthur Aron used to make couples in his laboratory fall in love. The post went viral, and we share them here with you – along with a few more:
Set I
1. Given the choice of anyone in the world, whom would you want as a dinner guest?
2. Would you like to be famous? In what way?
3. Before making a telephone call, do you ever rehearse what you are going to say? Why?
4. What would constitute a “perfect” day for you?
5. When did you last sing to yourself? To someone else?
6. If you were able to live to the age of 90 and retain either the mind or body of a 30-year-old for the last 60 years of your life, which would you want?
7. Do you have a secret hunch about how you will die?
8. Name three things you and your partner appear to have in common.
9. For what in your life do you feel most grateful?
10. If you could change anything about the way you were raised, what would it be?
11. Take four minutes and tell your partner your life story in as much detail as possible.
12. If you could wake up tomorrow having gained any one quality or ability, what would it be?
Set II
13. If a crystal ball could tell you the truth about yourself, your life, the future or anything else, what would you want to know?
14. Is there something that you’ve dreamed of doing for a long time? Why haven’t you done it?
15. What is the greatest accomplishment of your life?
16. What do you value most in a friendship?
17. What is your most treasured memory?
18. What is your most terrible memory?
19. If you knew that in one year you would die suddenly, would you change anything about the way you are now living? Why?
20. What does friendship mean to you?
21. What roles do love and affection play in your life?
22. Alternate sharing something you consider a positive characteristic of your partner. Share a total of five items.
23. How close and warm is your family? Do you feel your childhood was happier than most other people’s?
24. How do you feel about your relationship with your mother?
Set III
25. Make three true “we” statements each. For instance, “We are both in this room feeling … “
26. Complete this sentence: “I wish I had someone with whom I could share … “
27. If you were going to become a close friend with your partner, please share what would be important for him or her to know.
28. Tell your partner what you like about them; be very honest this time, saying things that you might not say to someone you’ve just met.
29. Share with your partner an embarrassing moment in your life.
30. When did you last cry in front of another person? By yourself?
31. Tell your partner something that you like about them already.
32. What, if anything, is too serious to be joked about?
33. If you were to die this evening with no opportunity to communicate with anyone, what would you most regret not having told someone? Why haven’t you told them yet?
34. Your house, containing everything you own, catches fire. After saving your loved ones and pets, you have time to safely make a final dash to save any one item. What would it be? Why?
35. Of all the people in your family, whose death would you find most disturbing? Why?
36. Share a personal problem and ask your partner’s advice on how he or she might handle it. Also, ask your partner to reflect back to you how you seem to be feeling about the problem you have chosen.
How long have you been in your career? How are you performing?
Professional stability, ambition and success may be important to you. Even if not, a difference in career objectives and trajectories can be a relationship challenge.
Best highly paid work-at-home jobs for moms
Do you enjoy it? Why or why not?
If personal fulfillment through your professional career is important, you likely will want someone with the same goals. Similarly, if you are working for the weekend, a highly ambitious partner may inspire you — or intimidate you.
What do you think about cheating?
This question is about how critical infidelity is to your boyfriend or girlfriend, how likely they are to forgive a cheat, and whether they are interested in open relationships or something casual.
What are your thoughts on therapy?
A commitment to self-exploration can be a very good thing — including openness to couples therapy should the need arise. Also, you may learn that a prospective partner is too over-reliant on counseling for your tastes.
How do you have fun with your inner child?
If the other person even understands the question, you are in business!
What are your hobbies? What role do your interest play in your life?
A person with a rich life outside of work and family, including sports, creative pursuits, travel, fitness, education make you attractive and interesting now, and can bring new experiences to your partner. Plus, a full partner makes a better, less needy and fragile partner.
What do you do to give back or volunteer?
The answer to this question illustrates whether your boyfriend or girlfriend's values are aligned with their life
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