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You Can Have a Win-Win Marriage: Use These 36 Questions to get on the Same Page



Once upon a time, my husband and I were not very good at communication and while we have not necessarily gone pro yet, we have greatly improved over the last few years. As our communication improved, I think it is probably obvious to you all, our relationship improved. I think one of the things that dawned on me is that by simply communicating, we could help both of us "win" in life, and create these win-win situations. Rather than trying to one-up one another on who is more tired or has done more, we could admit we were both tired and both had done a lot. Both of us need a break. We learned to do what I am teaching my preschooler right now, which is, take turns. Communicating helped us make sure both of our needs were met, rather than competing for time, resources, and naps.


There are three options that I can see when it comes to the dynamics of your relationship:

  1. Lose + Lose

  2. Win + Lose

  3. Win + Win


I know we all want a win-win, and it is possible. There is hope for this even if you find yourself in one of the other dynamics currently. We were probably in the win + lose category more than we would've liked.


Let's look at how we find ourselves in different dynamics:


Lose + Lose


Here are some of the characteristics that would be true of a lose + lose relationship dynamic:


  • Lack of Consideration (could be real or merely uncommunicated): You believe your husband/wife does not actively have your best interest in mind.

  • Lack of Trust: trust may have been broken in the past or one person may have a naturally untrusting and skeptical disposition (any enneagram 6s reading this? Holla!)

  • Lack of Communication: You couldn't help each other if you even wanted to because you don't know what the other person wants.

  • Lack of Goodwill: maybe the relationship has been injured by something big or by small things that began piling up so that you do not feel on the same team anymore.


Win + Lose


Here are some of the characteristics of a win + lose relationship dynamic:


  • Lack of a Good Perspective: If someone is particularly confrontational or argumentative, this could be a way of life to them. They might not be considering there even IS another way. Whoever the confrontational person is may feel like they need to "win" and have their spouse lose.

  • Lack of Conflict Resolution Skills: Maybe you know there is a better way (win + win), but due to a lack of skills you struggle to find out how to get there and feel like you must settle for a win + lose dynamic.

  • A season of Sacrifice: There are seasons in which one person may have to temporarily sacrifice for the good of another and in severe cases (like health) it may be long term. During times like these, the one who is sacrificing may feel like they are losing, but ideally this is temporary.


Win + Win


Some of the characteristics of a win + win relationship dynamic are:


  • Clearly known and communicated hopes, dreams, longings, and needs

  • Collaboration to ensure needs are met, responsibilities are done, and dreams are pursued

  • Mutual respect: Everyone's needs, dreams, longings, and responsibilities are all important and there is no need to measure or compare who has it harder or whose struggle is more legitimate

  • Emotional safety





John Gottman says this: "Every great love story is a never-ending conversation."



While a great love story is a never-ending conversation, many of us can get stuck in having a few of the same conversations on repeat that are not necessarily moving us forward or putting us in that win-win dynamic relationship.


Let me share a mostly related story, yet somewhat unrelated story to illustrate my point:


I have two kids, one and three years old. Kids have this superpower. Somehow they manage to make a mess in 30 seconds that will take you a solid ten minutes to clean up.


For example, drop a whole bowl of food on the floor. Dump out a whole container of toys. You get the point. It took them 30 seconds, and it will take me a lot longer. Ask them for help to get this reaction:





Sometimes I find myself walking around the house tidying it as the kids are still playing. I mean, it is vanity upon vanities. My one year old especially likes to get back out the very thing I just put away.


One day I was walking around tidying when it occurred to me that I needed to stop working in my life to work on my life.


I needed to stop tidying during this time, and do something that would actually make a real difference like decluttering, and remove myself from this vane cycle.


Here is where this story and getting stuck in the same conversation relate: We can get so stuck in our day-to-day life that we do not step outside of it and work on our LIFE life.


This can look like asking the predictable questions:

  • How was work?

  • How was your day?


But many of us do not move past and deeper than these everyday questions.

If we want to work on our marriage, we need to ask different kinds of questions.


The questions below are designed to:

  • Help you get on the same team

  • Get into an up-to-date conversation with your spouse so you are current on what one another really wants (because you and your wants do change)

  • Get the ball moving so you are both happier, more fulfilled, engaged in life, etc.


They ask where do you need support, what do you want, where are you now, and more. These are the kinds of questions that lead to a collaborative, value-led, growing life.



So, without further ado, here are your 36 questions:





  1. How many dates would you like to go on a month?

  2. What kind of experiences would you like to have as a family this year?

  3. What priorities would you like to focus on as a family?

  4. Are there any traditions you would like to start?

  5. How often would you like to have friends over to the house?

  6. How often would you like to get together with just your friends per month?

  7. What kinds of experiences would you like to have with your friends?

  8. What are some financial goals you would like to have as a family this year?

  9. What debt would you like to pay off this year?

  10. What would you like to save for this year?

  11. Would you like to earn more money this year? If so, how?

  12. Would you like to spend money on something fun/experiential? If so, what?

  13. How do you feel about your health? Physical, emotional, mental, and spiritual

  14. How would you like to work out this year (gym, bike, run, etc.)? How often and how long?

  15. Do you need to do anything to support your mental health this year? If so, what?

  16. Do you want to eat differently this year? If so, how?

  17. How is your sense of purpose? Do you need anything to support your spiritual health? If so, what?

  18. How do you feel about who you are?

  19. Are there areas you are trying to grow as a person?

  20. What do you feel like your current challenges are? How could I support or encourage you in those challenges?

  21. What/who is inspiring you lately? How so?

  22. How would you like to relax this year?

  23. What would you like to experience this year that is fun?

  24. If you could check 3 things off a bucket list/life list this year, what would you pick?

  25. Is there any place you would like to visit/go this year?

  26. Are there any hobbies you want to learn this year?

  27. Are there any topics/subjects that you would like to study deeper this year?

  28. How much would you like to read?

  29. Are there any classes you would like to take this year?

  30. How do you feel about our sex life?

  31. How do you feel about our communication?

  32. What do you love the most about our relationship?

  33. What would you improve in our relationship?

  34. How do you feel about work right now?

  35. Would you like to pivot or change within your career? If so, how?

  36. Are there opportunities you would like to pursue this year?


Here is what I have learned since we have been regularly communicating with these questions:

  • When you know what one another wants, you can work together so that you both get it. There are a ton more win-win situations when you know with clarity what you both want.

  • There is a lot less disappointment. Disappointment has been described as expectations minus reality. When you are in a constant up-to-date conversation (most of us are out-of-date with our husbands), our expectations start to match reality because our expectations are a lot more informed.

  • Moving in direction of your deepest dreams, longings, and desires starts with SPEAKING THEM. Not thinking about them, but speaking. I believe this is biblical. God spoke things into existence. Speaking is what gets the ball really moving. So I have learned if you want to live out your dreams, longings, and desires, you must first speak them to your husband.


I have heard the objections to a list like this:

  • "It feels too formal."

  • "It is too long."


But if you really think about it, it is less than one question a day.


My husband and I did this as a date, but you don't have to. Do what works for you. I only encourage not to take a look at this list, and think it is nice, and do nothing with it. It is what we do that changes our life and marriage. Not what we know or think about doing.


I hope this was a helpful resource to you.


God is a big fan of marriage and so am I. Rooting for you always.



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