I began thinking of things that I wish my husband and I had talked with each other about before we got married. We dated for two and a half years before marrying, but most of these conversations were not on our radar until much later- usually when a problem arose, and we had to fix it. How many fights we could have saved ourselves if we had talked about these things ahead of time!
Not to say that we don't still fight- of course we do. I don't think you could ever live with another person without some sort of misunderstanding or miscommunication coming up from time to time. But now that we understand these basic things about each other, we aren't starting from ground zero every time we get into an argument. I'm happy that we have made that kind of progress in the short time we have been married; I hope to say, fifty years down the road, that we have made much, much more.
I encourage you to do a few things with this list.
First, go through each question and reflect on your own answers. It's tough to understand someone else if you do not understand yourself. If nothing else, these are just some good questions to help you have a deeper sense of self-awareness and understanding.
Second, take one or two questions to your girlfriend/boyfriend or fiancé(e) (or to your spouse- most of them are still awesome conversations to have after marriage). Spark up a conversation and see where it goes. Tell them that you want to understand them more and explain why, and see if you can expand your relationship. I don't recommend trying to talk about all fifty in one sitting. I love to talk about these things, and even I would find that tedious. :)
And third, be conscious of the vulnerability that a lot of these questions bring. Some of them might be a little too heavy to start off with. Some people aren't comfortable rattling off such sensitive details, even to their significant other. Be understanding if your partner isn't ready to open up quite yet, and encourage them to meet you there when he or she is ready.
I hope you find these conversations to be helpful in developing and deepening your relationship. :)
1. What are the most important/memorable parts of your childhood?What are your first, favorite or most painful memories? Things you remember most vividly? Times you don't like to remember?
[The more you know about your partner’s past, the more you can understand how he or she developed into the person you know today.]
2. How do you feel about your relationship with your mom?Are you happy with it? What would you change about it? What do you love about it?
3. How do you feel about your relationship with your dad?[Same as above- knowing how your partner relates to his or her parents is crucial to empathizing and understanding him or her on a deeper level. It can help reveal some wounds or issues that may have come from either parent.]
4. How did your parents argue or fight?Did they yell? Did they leave? Did they fight fair? Did they resolve it? Did they never let you see them fight?
[The way your partner’s parents fought can give you valuable insight into habits he or she may fall into when you fight.]
5. How did your parents raise you?How connected did you feel to them? How were you disciplined? What kind of rules did your parents have? How strict were they? How do you feel about it now?
[Knowing how your partner was raised will give you an idea of how he or she might parent children someday- or possibly how he or she does not want to parent them.]
6. How do you want to parent your children? (if applicable)Do you want to raise children like you were raised? What would you keep? What would you change?
[Not everyone has the same idea of how to parent a child; do your ideas coincide with your partner's? Can you compromise with your differences?]
7. What do you prioritize?Work? God? Spouse? Kids? Other family? Write a list of your priorites and put them in order. What would win out against another? What is at the top of the list?
[Knowing your partner's priorities is very important. Do those priorities match up with yours?]
8. Do you want kids?If yes, how many? How long do you want to wait? How sure are you that you do or do not want kids?
[This is extremely important to know before you get married. Remember that you may not be able to change your spouses mind. Can you live with their decision? Can you compromise?]
9. What is your relationship history?What previous relationships have you had? How serious were they? How intimate were you emotionally and physically? Why did they end? How do you feel about them now?
[You should be aware of whatever significant relationships happened in your partner's past so that you can better understand any underlying ideas, expectations or wounds he or she may bring into your relationship.]
10. What are your religious beliefs/views on spirituality?What do you believe? How important are those beliefs to who you are? Do you believe the same things that I do? Do you expect me to believe what you believe?
[Again, don’t assume that you will change your spouse. Can you live with their belief system?]
11. What are your important political views?What issues are you passionate about? What issues are a trigger for you?
[While political issues may not be a big deal to some people, to others, they are very important. It's good to have the conversation and discuss any areas you may disagree on.]
12. What traditions do you value?Social/cultural traditions? Religious traditions? Family traditions? Personal traditions? How important are they to you? Why?
[Knowing what traditions your partner values will give you insight into what he or she will value. This may come up, for instance, when you plan to work on Christmas Eve, and your partner expected to spend it with you. Or it could come up when you want to sleep in on Sunday, and your partner expects to go to an early church service. These kinds of things are fixed earlier if you understand what the other person values and why.]
13. Where do you want to live? (or where won’t you live?)Why or why not?
[It’s good to know, for instance, if you want to live abroad someday and your partner absolutely will not!]
14. What are your career plans?What are your ambitions? Where do you want to go, eventually? How do you plan to get there?
[Do your partner's plans match up with your future plans?]
15. What are your long term goals?Where do you see yourself 5 years in the future? 10? 20? What do you want to accomplish in life?
[Can you mesh your partner's plans with yours?]
16. How do you handle money?Do you tend to spend it? Save it? Do you have any bad habits with it? Do you spend when you are emotional? Are you responsible? What is your history with money?
[The way your partner deals with money will be very important when he or she begins dealing with your money as a couple. If there are any problems, better to deal with them earlier than after the fact!]
17. Who has a lot of influence on you?Your mom? Your best friend? Your sister? Who has the ability to change your mind? Who influences the way you think?
[It’s important to know who your partner listens to and respects; it's especially important to know what kind of advice your partner will be receiving from those people, as one day he or she may be going to them for advice about your marriage.]
18. What are your expectations of sex?How often do you expect to have it? Who should initiate it? What if one of you doesn’t want to and the other does?
[The more in depth you understand your partner’s expectation of sex, the better off your marriage- and your sex life- will be.]
19. What are your expectations of marital roles?Who is responsible for what in the home? Who is responsible for what in your marriage? Who do you expect to fulfill certain relationship roles?
[Do those expectations match up with yours?]
20. What are your expectations of housework?Who is expected to do what chores? Who takes out the trash? Who cooks dinner? Who cleans the toilets? Who does dishes? Who does laundry?
[This was a very important question a mentor of ours asked us before my husband and I got married. Don't underestimate the power of hidden expectations! Knowing your partner’s preconceived expectations of roles in housework will save you many misunderstandings and fights later on!]
21. What are your "non-negotiables" in marriage?What is unacceptable, no matter what? What do you see as an "unforgivable" offense? What would be your response to it?
[It's crucial to know what things your partner will not tolerate in a relationship so that you can avoid problems before they happen.]
22. What are your views on divorce or separation?Do you think it’s acceptable? In what situations?
[Talking about your expectations for the longevity of your marriage is also extremely important. If one partner thinks that divorce should never happen, and the other thinks that marriage should end if the love is gone, they are coming into the marriage with two entirely different expectations.]
23. What is your view on marriage counseling or couples' therapy?Are you willing to go to it? Under what circumstances? Do you think it’s helpful? Who would you go to?
[Even if your marriage never gets to a breaking point, you may find yourself in need of a third party to help you work through some relationship problems. Do you and your partner see eye-to-eye about how those issues should be addressed?]
24. What are your expectations of my relationships with others?How often do you expect me to see my friends? How close do you expect me to be with friends of the opposite sex? How much information about our relationship do you expect me to divulge to others? What are your limits on my emotional or physical closeness with others?
[Whether it's with your coworkers, friends or family members, your partner will have some ideas of how close you should be to the people around you. It's important to discuss what his or her expectations are, and to assess if you are willing to respect those wishes.]
25. How do you tend to try to hurt others when you feel hurt?[When we feel cornered, we tend to aim to hurt others in the way that we would be most hurt by. Those who are most hurt by harsh criticism will be highly critical of others. Those who are most hurt by abandonment will try to make others feel abandoned. Those who are most threatened by being controlled will become very controlling. It's helpful to know what your partner's tendency is in this area so that you can recognize it when it arises, thus giving you more understanding into their mindset and giving you the opportunity to address their hurt. This is a habit your partner may not recognize in themselves offhand; you might find this out by observation, later.] 
26. How do you deal with boundaries?Do you have trouble saying “no” to certain (or all) people? Are you passive aggressive instead of direct? How do you react when people try to control you? Do you try to control others? Do you manipulate others? Do you let others say “no” to you without guilt or intimidation?
[Whether your partner lets others cross his or her boundaries, or he or she crosses others' boundaries, you should be aware of how they relate to boundaries in general. The boundaries they set for others and accept from others will give you a look at how they will set and accept them in your relationship. Again, this may something your partner is unaware of, unless they have already reflected on it.]
27. What do you admire in other people?What traits do you respect? What do you think are good traits to have?
[The things we admire in others shed light on our values. If you admire honesty in someone, it's likely that you aim to have integrity in your own life. Likewise, if you admire less-than-desireable traits (such as respecting a person for "telling someone off"), it raises a red flag on values that may be misplaced.]
28. What can you not tolerate in other people?What bothers you about people? What puts you past your limit? What do you think are bad traits to have?
[Just as it's important to know what your partner admires, it's also important to know what traits he or she disapproves of, so that you can again see where their values lie.]
29. How do you relate with people I care about?Do you like them? Can you get along with them? What do you think about them?
[If your partner has issues getting along with people whose opinion you highly value, you must decide whether you value your relationship with your partner or the other person more; because there will likely be a time where you may have to choose between them. Are you willing to choose your partner?]
30. How do you react when other people are hurting?Do you naturally notice it? Does it scare you? Does it make you uncomfortable? Do you feel hurt to see them hurting? Do you jump to help them?
[Knowing how your partner responds to others' pain will give you insight into how he or she will respond when you are in pain.]
31. How do you respond to stress?Do you become angry? Perfectionistic? Withdrawn? Impulsive? Critical? Irresponsible? What kinds of things do you do or say?
[It's important to be able to recognize when your partner is acting under stress, so that you can be helpful and not hurtful to them.]
32. How do you respond to conflict?Do you like to argue? Does it bother you? Are you willing to face conflict? Do you avoid it? Does it intimidate you? Do you fight fair? Do you yell? Do you intimidate? Do you withdraw?
[Knowing how your partner fights will be very important as you navigate arguments and disagreements throughout your relationship. If there are inherent issues with how he or she deals with conflict, it is much better to work with them ahead of time, rather than waiting until the problem arises.]
33. How do you respond to grief?Do you cry? Do you need to be alone? Do you need to talk about it? Do you become angry? Are you hard to talk to? Do you open up about how you feel? Do you let yourself feel negative emotions? What do you do to make yourself cope?
[Unfortunately, every relationship is bound to cross a bridge where one or both of you will face tragedy of some sort. It's important to know how your partner will respond in these situations so that you can anticipate the reaction and be able to work with it.]
34. What helps you de-stress?What do you do when you need to blow off steam? What activities help you feel better? What gives you relief from stress?
[There will be times where your partner needs to calm down and do something to relieve tension. Knowing what helps your partner can not only give you more understanding into the things he or she will do at these times, but can also give you the opportunity to be helpful if need be.]
35. What makes you feel loved by others?What things do people do that make you feel most appreciated or loved? What is the most loving thing someone has ever done for you? How do you know someone cares about you?
[Understanding your partner's "love language" will not only help you to keep your connection strong and help them feel loved, but it will also help you solve problems down the road when you may not be "speaking their language."] 
36. How do you show others love?When you want someone to feel loved, how do you show them? What meaningful things do you do to convey your feelings for others?
[Usually we show love in the same way we receive it, but sometimes it can differ a little. Keep in mind how your partner shows love; someday, when you are feeling neglected, remember to look for the ways that he or she shows love- not just the ways you naturally receive it.] 
37. How do you learn things best?What is the quickest or best way for you to learn something? Do you need to talk it through? Hear it out loud? Try it yourself?
[Understanding how your partner learns best can help immensely when you are trying to work together on something.]
38.What makes an apology feel genuine to you?How do you know when someone is really sorry? Do they need to be regretful? Do they need to say they were wrong? Do they need to do something to make it better? What makes you feel like the issue is put to rest?
[It’s really important to know your partner’s “apology language.” People value different things in apologies; so you may apologize to your partner genuinely, but if it lacks what he or she values in an apology, he or she may think you are insincere. Understanding your differences in this area will help you to resolve and avoid many fights in the future!] 
39. How do you see yourself?What is your “identity?” How would you describe yourself, in a nutshell? What is your personality like? What do you think about your appearance?
[Does your partner's idea of who they are match up with how you see them? Why or why not?]
40. What do you dislike most about yourself?What traits do you wish you didn’t have? What traits do you try to get rid of? Physical traits? Personality traits?
[Understanding what your partner dislikes in themselves can give you a heads-up for sensitive areas you should know about. You may not agree with the things they dislike, but it will help you understand how they feel about themselves.]
41. What do you most value in yourself?What traits are you proud of? Physical traits? Personality traits?
[Just as it's important to know what your partner dislikes about themselves, it's also important to know what they like about themselves. These are the things they will likely value most and will keep around.]
42. What emotionally recharges you?When you are mentally exhausted, what gives you energy again? Brainstorming new ideas? Making lists? Going to coffee with a friend? Doing something physical? What makes you feel like “yourself” again?
[It's so helpful to know how to help your partner recharge- especially if their way of recharging does not match up with yours]
43. What emotionally drains you?
What wears you out fastest? Social events? Too many plans? Dealing with someone else’s emotions? Being alone for too long?
[If you know what will drain your partner, you can be sensitive to those situations and anticipate them needing some time to recharge afterwards.]
44. Are you more comfortable sticking to structure or leaving room for plans to change?Do you like predictability or spontaneity? What makes you feel more at ease? What makes you feel frustrated?
[If your partner's answer is different than yours, understand that you will need to compromise at times to be sure that both of your needs are met.]
45. Does it come more naturally to you to make decisions based off of what is fair and logical or based off of what you feel?Do you find yourself thinking in terms of logic or feelings? Do you tend to be more of a “thinker” or a “feeler”?
[So many misunderstandings in communication root out of a basic difference in how we make decisions! If your answer differs from your partners, understand that there will be times that you will not see eye to eye about how things should be done. Mutual respect and lots of patience and communication will be necessary to get things done in these situations.]
46. What triggers your anger?[It’s good to know where these emotional bombs lie, so you can avoid them when you should, and approach them sensitively if you need to.]
47. What embarrasses you?[Sometimes people are embarrassed by things that we never would guess. In order to avoid humiliating your partner unintentionally, it’s important to know what kinds of things embarrass them.]
48. What are your biggest temptations?What do you struggle with most? What do you have a hard time saying “no” to? Are you able to say no? What do you do to deal with the temptation?
[Understanding where your partner is weak is crucial to helping support them. Knowing what they struggle with can also shed light on areas where you may not have seen a problem before.]
49. What is your deepest desire?[Every person has something that they deeply need. Some desire to be good and have integrity, others to be loved and needed. Some desire to be unique and true to themselves, others to be valuable and successful. Some need to feel secure, others to be happy, others to be competent. Some desire to protect themselves, and some to find inner peace. What is the thing that your partner searches for above all else? This will give you a very important insight into his or her motivations, feelings and actions. This is a very deep and vulnerable thing to ask someone, and it is something that not everyone will have an understanding of. Don’t expect your partner to know right away, but aim to understand it if you can.] 
50. What is your deepest fear?[Just as everyone desires something, everyone fears something too. What fear is most terrifying to you? Do you fear that something is wrong with you or that you lack inherent value? Do you fear that you are unworthy of love? Do you fear that you do not have an identity or that you are incompetent? Do you fear being trapped in pain? Losing support? Losing connection? Do you fear being controlled? Like the previous question, this is very sensitive ground to tread on and should be treated as such. Be respectful if your partner is not able or willing to reveal such a vulnerable part of his or herself to you yet, but encourage them to share it with you when they are ready! This is something that will help your relationship grow so deeply, if you are willing to be understanding of the other’s fears. When we know what people fear, we know why they act the way they do. We can understand them and empathize with them on a much deeper level, and our relationship becomes much stronger.] 
What about you? Were there any things you wish you would have talked to your spouse about before you married? Add anything you think should be on the list!
You might also like: Things To Do Before You Get Married (That Actually Matter)
 The Wisdom of the Enneagram: The Complete Guide to Psychological and Spiritual Growth for the Nine Personality Types, by Don Richard Riso and Russ Hudson
 The Five Love Languages: How to Express Heartfelt Commitment to Your Mate, by Gary Chapman
 The Five Languages of Apology: How to Experience Healing in All Your Relationships, by Gary Chapman and Jennifer Thomas