The Tough Questions That Need to Be Asked Before Considering Marriage

In the beginning relationships can seem like all roses and fun, but in reality, whether you’ve just begun seeing someone or you’ve been dating for a while, a healthy relationships requires effort and in the beginning especially, lots of discernment. 

Let’s be honest, it’s easy to get swayed by the excitement of a new relationship and the butterflies that come along with new affections. Sometimes you may feel so head over heels in love that you don’t even “want” to ask the hard questions, because you so desperately want the relationship to work out. I know, I’ve been there before.

However, with the increase of domestic violence and abuse (1 in 3 women and 1 in 7 men have been abused by an intimate partner), as well as the increase in addictions (sexual or substance related), it’s important to enter into relationships with Christ’s words at the forefront. He cautions us all with these words: “I am sending you out like sheep among wolves. Therefore be as shrewd as snakes and as innocent as doves.” (Matthew 10:16)

I know it may seem “unloving” to feel like you need to be on “guard” in the beginning of a relationship, but really you are simply using your God-ordained and given wisdom to discern between a healthy relationship and a potentially unhealthy one. God would approve of this. It would be far more loving to end a relationship that isn’t best for you early on rather than years later after having invested a great deal of time, energy, and your heart.

I don’t think Jesus said the words above to frighten us but rather to make us aware that not everyone, (no matter how charming they may seem), will have our best interest in mind. I’m also not sharing these things because I think you should to distrust all people. In fact, I hope this information will help you weed out any unhealthy relationships in order to make room in your life for the man who will be the best and healthiest match for you!

Sadly, I’ve seen it happen many times: a woman falls in love with the man she believes is safe and who will truly love her back, only to end up living through years of pain, heart ache, and sometimes even fearing for her own life. I’m sharing so hopefully other women won’t have to walk down that path. 

Setting a Foundation for Your Decisions 

So, let’s jump in. I’m going to share some of the more some difficult questions to ask which fall under six categories, that you can (and hopefully will at some point) ask before considering getting serious with anyone. These questions are in addition to any other routine dating questions that you might find in a book on dating or relationships. These are also the questions that generally aren’t discussed in your church, but that should be (at some point), because they reflect very real, common marital problems.

I hope by addressing these things early on, you’ll be able to weed out anyone who sends off warning signals for you based on their answers. 

Now, I believe this goes without saying—but I’ll say it just in case, even after doing your very best to discern if a potential mate is “safe,” unfortunately there are no hard and fast guarantees. But, by asking these questions, hopefully you’ll at least have a better foundation from which to make the best possible decision about marriage and your future with the person you’re dating. 

(*Note this article is addressing women dating men, but could be altered and used for a man dating a woman.)

Questions to ask while dating:

  1. Relational History Taking: “How many women have you dated?” “What was the reason for each breakup?” “Have you ever pursued a past girlfriend once the relationship ended?” (ie. you’re asking if they’ve ever stalked someone, without using the word stalking, remember Christ calls us to be “wise.”) “What did you dislike most about your past girlfriends?” “Do you feel jealous when I speak to other men?” If you do feel jealous, when do you notice that feeling?” “Do you find yourself worrying that other men are looking at me inappropriately?” “Do you worry about what I’m doing when I’m not with you?” “Have you had any friendships that ended badly, can you share about those?” “Tell me about your relationship with your mom, your dad, your siblings?”

With these questions, your goal is to get a “historical” picture of their ability to hold down a healthy relationship, as well as how they are internalizing your relationship. You also want to listen out for serial dating where every relationship seems to have ended because of the “other” person, or if the person you’re dating always comes across as the “victim” in each relationship story. While it’s possible that they truly weren’t the one at fault in each case, if they’ve had many relationships and it was never their fault, this is a red flag. It could mean either they were at fault and possibly don’t realize it or don’t care, or they could be operating out of a “victim mindset.” It could also mean they now have extremely low self-worth if they’ve been in repeated abusive relationships or that they could be struggling with ongoing codependency issues. All of which should at the very least cause you to pause and consider what your future will look like together.

In regard to your partner’s relationships with family, specifically close family, you can (and should try to) learn a lot. You are looking for indicators as to whether or not there was abuse in their family of origin (either witnessed within their parent’s marriage or they or their siblings were abused in some way). Does your partner have a healthy attachment to his parents or not, and if not, why not. You’re also listening for any “unresolved” family issues or dynamics. Statistically speaking, though it’s not a given, it is not uncommon for men who have come from homes where there was either child abuse (sexual, physical, or emotional) or where they witnessed domestic abuse or violence that they can relive and act out these patterns once they are in a committed intimate relationship. You can also learn a lot about your partners views on women from hearing and observing how he treats his own mother. 


2. Financial History Taking: “Are you currently in debt, and if so how much debt?” “Have you ever struggled with gambling?” “How do you feel about equally sharing the finances in a marriage?” “How do you envision our finances should be shared or handled if we were married?” “Do you trust me with money?” “What does your job history look like?” “What are the reasons past jobs didn’t work out?”

With these questions, your goal is to get a “historical” picture of their ability to hold down a job, to manage their money well, or to address any patterns that indicate a larger problem such as gambling, financial impulsiveness, or a high need for financial control in the relationship. Beyond this, you also want to get a picture of how your partner relates in the work world and in team settings. Are they able to get along well with others, or do they have a history of numerous jobs where they were asked to leave or were even fired?


3. Emotional History Taking: This is where you would ask any questions relating to your partners past emotional stability. Listen for things that could indicate: impulsivity, extremely low self worth, unresolved shame, or inability to control emotions, etc.

“Have you ever lost your temper with someone, could you explain?” “How do you handle stress?” “What things stress you out?” “Have you ever struggled with anger issues, explain?” “Do you or have you struggled with depression, when and what was going on at that time in your life?” “Have you ever contemplated or attempted to commit suicide?” “Have you ever been to see a psychologist or counselor, if so, for what?” “Have you ever been diagnosed with any mental illness, if so which one(s)?” “Have you ever been arrested, if so for what and when?” “Have you ever been violent in any of your relationships?”


4. Morals, character formation, and faith questions: This is about as important as anything listed above, these are the questions that truly address a potential partner’s “heart” condition.

“How do you feel about women?” “What do you see as their role in life, in marriage?” (Many men who end up abusing a woman have a low view of women in general—though they may or may not admit this.) “If I ever feel unsafe in our relationship, how do you feel about me talking to someone about that?”

Also ask questions related to your faith, that would clue you into whether or not you would be “equally yoked” in your beliefs. “How do you feel about God?” “How would you go about sharing your faith with our future children?” (Listen to any indicators that would suggest “forcing” beliefs onto your children vs lovingly sharing beliefs and allowing for age appropriate choice). “How do you believe children should be raised in general, what are your views on disciplining children?” “What do you believe is the best way to handle disagreements or conflict in our relationship?” “Have you ever stolen anything, if so, what was it, and did you take steps to make it right?” “How do you feel about little white lies?” 


5. Pornography/Substance Addictions: “Are you currently or have you looked at p*rnography in the past, and if so how frequently?” “How do you feel about p*rnography—do you think it’s an acceptable thing?” “Are you comfortable with me having the passwords to your computer/email?” “Are you currently or do you have a history of abusing drugs/alcohol/prescription drugs?” “How do you feel about drugs/alcohol?”

You alone get to decide if ever viewing p*rnography or using substances in the past is a deal breaker. But my suggestion is to seek first for the ideal. The ideal being that they have never participated in either. However, if you know your partner may have been exposed to or experimented with one or the other, or both, but feel certain it was an isolated event or something resolved from their past—and you want to move forward, then I would suggest the following. Listen for patterns and assess the situation surrounding your partner’s exposure—as well as their response to the exposure. Was it one time occurrence where maybe they were presented with it by a “friend” as a teen, or maybe (in the case of p*rn) it came up on the computer and they quickly shut it off? Or was it more serious, for example: it was related to a sexual molestation situation, or a part of their childhood for many years up until now, etc? You could also listen for what happened when they were exposed to p*rn or substances. Were they intrigued and continued to seek it/them out, or were they repulsed and they quickly turned away from it/them? Was it something they had a problem with, but can clearly share how they took steps to overcome it, and are now willing to have you or someone else as their accountability partner.

These are not a fool-proof questions, because unfortunately, many people who are addicted to porn or any other substance can have a tendency to self-protect and “cover the truth.” They may even think they are past their problem since they haven’t viewed p*rn or used substances while dating you, or that they will surely be able to overcome it if the relationship continues. However, if either of these is already a problem in their life, no relationship will help them to stop using these things unless they have some sort of intervention to do so: often lengthy counseling and therapy, or some kind of conversion of the heart on their own accord. This is something they have to “choose” on their own to stop participating in. You should never be someone’s impetus or reason for changing an ongoing destructive behavior. If you are, it’s likely the results will not last.

Aside from dealing with “a wolf in sheep’s clothing,” you will hopefully be able to tell if your partner is an honest person at heart and if they’re being open with you in their responses to your questions. If you don’t sense they’re providing you with full disclosure, I encourage you to kindly probe more until you’re satisfied that you’re receiving honest answers. If you sense that you aren’t, then this would be a red flag that would warrant reconsidering the relationship.


6. Sexual issues: past or present. This would include things like: masturbation problems, or excessive past sexual relationships, or a lack of faithfulness in past relationships.

“Have you ever cheated on someone you were dating or married to?” “How many women have you been physically intimate with?” “Have you ever paid a prostitute for relations?” “Have you or do you currently masturbate, and if so how frequently is this occurring?” If you even slightly wonder if they have had or do have current same sex attractions, don’t hesitate to ask this question as well.


While I know for some women (young or old) these questions may seem “too forward” to ask. I also know some young Christian women who were raised to never be alone with a young man until marriage—if this is you, you may be thinking I could never ask these questions in front of others! I agree, that would be very difficult. But, I would encourage you then to bring along a wise other, either a trusted parent, a counselor, or a Pastor if needed while you work through these things together. If this scenario doesn’t describe your situation, but you’re still uncomfortable with these types of questions: let me assure you, you want to know these things prior to deciding if you’ll spend the rest of your life with someone. Never be embarrassed to ask the hard questions, because healthy marriage is built on being transparent, consider this practice. 


A Few Things to Note:

Now clearly, you wouldn’t want to approach your partner like you’re the Gestapo asking tons of interrogative questions…or “dump” them on him all in one sitting. But, I do feel these are good questions that need to be addressed—at some point, but definitely before saying “I do.” I also feel like they provide a good “starting” point to begin thinking about the other things you might want to discuss before considering marriage. However, these questions are not exacts but more of a rough outline of some things to think about.

Something else to note: don’t allow your own past to lead you into accepting big glaring problems in another person. I have worked with many women who had a history of past sexual encounters, or perceived “failed” relationships in their past, and it has greatly diminished their self worth. If this is you, it can lead you to subconsciously lower your standards in what you’re willing to accept in a future potential partner. This happens often because of an internal monologue that says, “Well I’ve certainly not been perfect, how can I expect higher standards from someone else?” 

But, let me set the record straight: you are worthy of holding out for God’s very best for you—no matter what you’ve done (or someone else has done to you) in the past.

While it’s important to “ask the right questions” of the person your considering entering into a lifelong commitment with, I think it’s just as important to ask the right questions of yourself. It’s vital to search your own heart and also ask yourself some hard questions. This is another part of helping to ensure you have a better chance for a healthy marriage. For a list of things to consider regarding your own heart and motives while dating, Click Below:

Beyond questions that can be asked either of your partner or yourself, I also believe that much can be discerned about the person you’re dating by observing their actions. So, with that in mind, I’ve also compiled a “Red Flags Checklist for Dating,” which will be linked here once it’s complete.

I would love to hear your thoughts on the things you wished you had asked before marriage—-or the questions that you’re asking while dating. So, feel free to share those in the comments as well, so that other women can learn from what you’ve learned!


Darah Ashlie

Hi, I’m Darah! If you’re joining us for the first time, welcome, I’m glad you’re here. I’m an Abuse Recovery Coach as well as a Board Certified Christian Counselor whose passion is to help women go from surviving to thriving. On the blog I share how you can get out of feeling stuck and overwhelmed, relationally and emotionally, and start to live like an overcomer!



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