Derisking Marriage

The Gist: Due diligence before “I do”

A review of multiple books and sources, including Things I Wish I’d Known Before We Got Married by Gary Chapman.


Congratulations! You’ve found the person you want to spend the rest of your life with. As we discussed in our last correspondence about getting serious if you’re single, this is a big deal and very worthy of celebration.


But the thing about love, especially in the early years, is that the nights are brighter, the grass is bluer, and the sky is greener. In that love is blind, love distorts. You look past every defect and think you can overcome every obstacle because love conquers all. But before you get married – a contract that should last a lifetime – you should take a hard look at those defects and obstacles because they’ll become real soon enough. 

Naturally, if you are en route to getting married, you think your person is pretty swell – but bear in mind that practically no one who gets married is planning on getting divorced. Divorcees at one point thought their spouses were pretty swell, too.


Figure 1. Exceptions include gold-diggers and green-card-chasers. 


Put another way, imagine the due diligence you’d want to do before buying a home you’d live the rest of your life in. Gosh, the property seems dreamy – but will you still love the style when it’s a few decades old? Can the layout and location accommodate your needs as a professional, a parent, a retiree? Are you certain that the internal structure is sound? Again, remember that who you marry is just about the most important decision in your life – and that as annoying and expensive as a home remodel can be, it’s infinitely easier than trying to do anything similar with your spouse.

Six million dollar man

Figure 2. Note that, with inflation, the Six Million Dollar Man would actually be more like the Thirty Eight Million Dollar Man. Even then, his bionic improvements were all physical and he looked like Lee Majors even before his accident. Of course, if you’re just looking for a more attentive husband, maybe you can pay an electrician a few bucks to administer some shock therapy.


As Ashley and I dated, we always talked about the prospect of marriage – but as we approached the time when it might be a near-reality (a proposal should not be a surprise), we spent every Saturday morning for months talking things through: 


Will we be good friends for a lifetime? 

Will we assume the best about each other and work on problems and opportunities together? 

Will we be good parents whose qualities we want our kids to inherit? 

Are we willing to sacrifice for each other?


All of which are admirable qualities. But we also talked in detail about how we argue, how we’d divide family responsibilities, how we felt about money and ambition and religion and autonomy and any number of ideas. We hypothesized how we would react if various problems arose and we talked about how we might deal with the opportunities and challenges that life might bring us, including what kind of values we might want to raise our kids to live up to, assuming we could be blessed with them.


Figure 3. In one instance, Ashley’s heart poured out about raising kids to be independent and work hard and love God and their country and be exceptional in whatever they chose to be. After hearing that, I simply added, “And to take care of their parents.”


We also took a hard look at our odds. Daniel Kahneman, the psychologist who won the Nobel Prize in economics, suggests that before you take on any venture you should find the base rate of success for people who do something similar to ensure that you have the appropriate expectation – and then try to reason as to why you might be different from the average. From there, you can accept or reject the gamble. 


At first, it seems daunting: about half of marriages end in divorce. And divorce is bad, as bad as cigarettes for your health. If you end up having kids, they’ll suffer too – in their academics, mental health, and eventually in their own relationships. And, as one satirical twitter account has observed, marriage means you’re betting 50% of your future net worth. Which seems like maybe a good deal for the other party, except that the lower income earner tends to fare worse after a divorce.

But take a closer look at the data and how it applies to you. 78% of women with a college degree remain with their first husband for over 20 years (the length of the study). Generally, only 41% of first marriages end in divorce (compared to 60% of second marriages and 73% of third marriages) – in other words, though half of marriages do end in divorce, most people who get married stay married. If you’re wealthier, if you’re conservative, if you’re a practicing Christian, if you’re Asian, if you have a high IQ,  if you marry after age 25, divorce is less likely. And if you can’t be all those, try to find someone to marry who is.

Crazy rich asains

Figure 4. The best marriage manual on the market turns out to be Crazy Rich Asians.   


There are lots of other stats out there: those who live separately before marriage are less likely to get divorced; meeting in a bar is more likely to lead to divorce; those who delayed sex until adulthood and those with fewer lifetime sexual partners are less likely to get divorced. Certain professions are more likely to get divorced – dancers, bartenders, massage therapists, Navy SEALs; others, less likely – farmers, clergy, certain kinds of doctor. The bigger the age gap between you and your spouse, the worse. If your parents are happily married, you’ve fortunately got a better shot of being happily married yourself. If your parents are divorced, you’ve unfortunately got a better shot of being divorced yourself. 

Amusingly, the more people you invite to your wedding, the less likely you are to get divorced — but the more you spend on your wedding, the more likely you are to get divorced.  Also: Men who have good relations with their in-laws are less likely to divorce while women who have good relations with their in-laws are more likely to get divorced. 

Some of these things you can change – and though rather famously correlation is not causation, I’ve always figured why not lean into the correlations you like? If you’re starting early, turns out the conservative lifestyle has nice life outcomes: delay having sex until adulthood and then be choosy, look hard in college for a spouse, date for a couple of years but don’t live together, and get married after you turn 25. Even if you’re already married, you can derisk when you quit drinking, avoid divorced friends and coworkers, stop using social media, make more money and spend less of it, become a farmer (apparently an unusually successful one), watch romantic movies, have sex about once a week (with your spouse, I should note), go to church weekly but move away from concentrations of Evangelical protestants, and if and only if you’re a woman, pick fights with your in-laws. 

I am only joking a little. These kinds of statistics are fun and sometimes strange but they can be genuinely helpful in making the right decisions and finding the right spouse. And, perhaps most importantly, if you look at these statistics and discover that the correlations are going the wrong direction – that, for example, you’re thinking of marrying a divorced dancer you met in a bar – you should abandon your efforts or move forward with particular vigilance knowing that Vegas would bet against

I am about to share the questions that Ashley and I asked each other before we got engaged but although I think marriage is awesome and that you should get serious about searching for a spouse, it’s okay not to get married to the particular person you’re with right now. If you go through due diligence before you get married and you discover that the odds are stacked against you or the answers to basic questions start to unnerve you, it’s better to start your search anew than invite all your friends and family to a big party and then subsequently divorce. Indeed, if you have any doubts at all, discuss them, if not with your significant other, with someone else you trust. At the same time, acknowledge the real and flawed human being you are spending time with, fairly compare them to others you’ve dated, and don’t let the perfect be the enemy of the good. 

Even before Ashley and I went over the questions below together, I tried to figure out the answer by myself by running through a series of questions inspired by Kahneman to push past cognitive biases. I asked fundamentally what the first principles of being married were about and how well they applied. I quickly concluded that my relationship with Ashley was my best ever – so getting married was a good example of pouring gasoline on fire (and leaning into the math of romance). I worried about being so in love with Ashley that my perspective was skewed. But, borrowing an analogy from my work in the apartment building business, I determined that Ashley’s replacement cost was sky-high!

Anyway, take a look at the questions below and adjust them for your own use – in particular, you should expand any section in which there is more concern and/or in which the odds are not in your favor. 


  1. Do we agree that this is perhaps the most important decision in our life and that we want to seriously and truthfully explore whether we are right for each other?
  2. First Principles
    1. Will we be good friends for a lifetime? 
    2. Will we assume the best about each other and work on problems and opportunities together? Will we be partners in success? 
      1. Recommended reading: Seven Principles for Making Marriage Work
    3. Will we be good parents whose qualities we want our kids to inherit?
    4. Are we willing to sacrifice for each other?
      1. Recommended reading: The Meaning of Marriage. A quote: If two spouses each say, “I’m going to treat my self-centeredness as the main problem in the marriage,” you have the prospect of a truly great marriage
  3. Why we’re here: be as expansive and as mushy as you’d like – get all the feels down on paper and you can look back in the years to come and remember the spark that started it all. And, of course, you can look here to weigh any doubts against.
    1. Why Grant loves Ashley
    2. Why Ashley loves Grant
  4. Zooming out and looking at the base rates of success for marriages, what do our specific chances look like? Where are we swimming with and against the odds? How are we different from the averages described? What is within our control? How can we strengthen our positives and derisk our negatives?
    1. Probably the best resource is this compendium of divorce facts and figures: 
    2. But there is plenty out there and you might want to especially investigate anything that particularly affects you. Answering this question takes the most outside work – but it’s really rather important as a reality check. And once you’ve got your answers, adjust the scope of the remaining questions accordingly. 
  5. Marriage models:
    1. What is the role of a wife and a husband?
    2. How did your family divide responsibilities growing up? What roles did they play?
    3. How did your family argue? Did your family throw plates, calmly discuss issues or silently shut down when disagreements arose?
    4. Name and discuss two unrelated couples that you admire and would hope to emulate.
  6. Agreement and conflict:
    1. What do you want to do with your life? What are your biggest dreams and how does our relationship fit into them?
    2. How will we make decisions together?
    3. How can we best tell each other when we’re upset and resolve it in a way that respects each other?
    4. Will we turn toward each other when arguing? Are our conflict management styles compatible? Why do you think we avoid or confront?
  7. Religion:
    1. Have we reached a clear understanding of each other’s spiritual beliefs and needs?
    2. How are we going to live this out in our life?
    3. What does our religion expect of our marriage? How does our religion inform how we should conduct our relationship?
    4. How can we best pray for each other?
    5. What does our ideal community of faith look like?
  8. Children: 
    1. Are we going to have kids? If so, when? How many? How far apart?
    2. Parenting models: what is the role of a mother and a father?
    3. What beliefs do you have about yourself that resulted from your childhood? If you could change anything about the way you were raised, what would it be and why?
    4. How will we divide child rearing responsibilities?
    5. What values do you want to teach our kids?
    6. How would we teach religion to our kids?
    7. Should we always tell our kids the truth? (About Santa, for example)
    8. How would we want to discipline our kids?
    9. How would we go about educating our kids?
    10. How will we teach our kids about money? How will we financially support our kids?
    11. What would we do if we could not have kids? If our child has severe disabilities? If our kid does drugs? Rejects our religious principles? What else might be a challenge? 
    12. How are we going to get to know best practices for raising kids?
    13. Will we take care of ourselves as much as we take care of our kids? How will we prioritize our own relationship as spouses amidst parenting? 
  9. Money:
    1. What is the best way of going over our finances so that we can be completely transparent with each other? (Current net worth, fixed monthly overhead, debt, savings, investments, etc.)
    2. What is the purpose of money? What do we want to do with it?
    3. What does our spending preference look like? What’s the most we’d be willing to spend on a car, couch, shoes? How much are we prepared to save? Should we strictly impose budget rules about how much of our monthly income we will spend? (And on what?)
    4. How will we manage our money? Who will manage our money? What’s our risk tolerance? How do we feel about debt?
    5. Should we have separate bank accounts?
    6. Will we both work? How should we contemplate major career decisions? What does work/life balance look like?
  10. Lifestyle: Do we share the same vision of life together? 
    1. What are the perfect and the typical weekday evenings?
    2. What are the perfect and the typical weekends?
    3. How should we spend time off? How often should we travel for a vacation, visit family?
    4. What do we enjoy doing together and separately? How much autonomy should we have on a week to week, month to month basis where we spend time apart? Can you deal with my doing things without you? 
    5. Where precisely are we going to live? What does our ideal home look like?
    6. How will we maintain our home and divide responsibilities for chores? 
    7. How would you like to change and how does our relationship fit in?
    8. How will we decide what to eat?
    9. Will our home have a television? A pet? Alcohol?
  11.  Family and friends:
    1. Will we consistently choose each other over our parents? Do we value and respect each other’s parents? Do either of us have any concern about parents or in-laws interfering with our relationship? What does my family do that annoys you? How will we resolve differences between our families? How will we care for aging parents?
    2. Do we like and respect each other’s friends? Anyone of particular concern? How often will we socialize? 
  12. Health:
    1. Do we fully understand each other’s emotional and physical health, as well as family history? Do we have any experience with addiction?
    2. When you are sick, how do you want others to respond to you? When a significant person in your life is sick, how do you respond?
    3. How will we work through real tragedy (e.g. death of our parents)?
    4. Are we willing to diligently pursue calm? How can we best tackle day to day stress?
  13. Familiarity: Don’t marry a stranger
    1. Has dating and being in love been a close enough approximation of a future relationship as a married couple and introduced major fault lines? Do we need more time?
    2. If I could live your life for one day, what do you think would surprise me the most? 
    3. Do you think Younger You would be happy with what you have become? 
    4. What are the highs and lows of your life so far?
    5. What would be one thing you’d change about our relationship? 
    6. Are there things I say or do that make you want to spend less time with me? 
    7. When do you feel most loved? Are we familiar with each other’s Love Languages?
    8. How do we keep love alive?
    9. Can we comfortably and openly discuss our sexual needs, preferences, and fears? 
  14. Commitment:
    1. What is your greatest fear or concern about being married? What have you done to address these concerns?
    2. What are our honest feelings about divorce and under what circumstances we would consider it?
    3. Will our experiences with our parents help or hinder us? Will our experiences with our exes help or hinder us? What have you learned?
    4. How will we be vigilant in protecting our marriage, especially from adultery?
    5. Are there some things that you and I are NOT prepared to give up in the marriage?
    6. If our marriage runs into trouble, what are we prepared to do to work on them? Would we go to counseling?
    7. Have we been completely honest with each other? Is there anything that the other person should know but does not?
    8. Are we confident in agreeing to a contract in front of our family, friends, and God to be with each other for the rest of our lives?
  15. Returning to First Principles
    1. Will we be good friends for a lifetime? 
    2. Will we be partners in success? Will we assume the best about each other and work on problems together?
    3. Will we be good parents whose qualities we want our kids to inherit?
    4. Are we willing to sacrifice for each other?
questions before engaged

Figure 5. Click here to acquire 101 Questions to Ask Before You Get Engaged (7.5/10). Focused on Christian couples, there is a mix of questions good for anyone and those specific to the Bible. I’ve incorporated some of the best above, but there are other provocative questions here: What are five reasons a person would want to spend the rest of their live with you, and three reasons they wouldn’t? Who are the people in your life you’ve needed to forgive and how did you accomplish this?

things I wish I'd Known

Figure 6. Click here to acquire Things I Wish I’d Known Before We Got Married (8/10). Also from a Christian perspective, though has a fairly broad application. By Gary Chapman, who also wrote the Five Love Languages. Especially good at discussing the two stages of love – the initial brain chemistry euphoria in which everything is easy and the following reality that requires intentionality but is far more rewarding. 


Thanks for reading! If you enjoyed this, forward it to a friend: know anyone seriously dating and thinking about marriage? How about someone engaged? Or anybody who hasn’t found the right person yet but is looking ahead?

For more, check out my archive of writings, including my review of the Five Love Languages. 

I read over 100 non-fiction books a year (history, business, self-management) and share a review (and terrible cartoons) every couple weeks with my friends. Really, it’s all about how to be a better American and how America can be better. Look forward to having you on board!

    2 Replies to “Derisking Marriage”

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