When is the best time and way to bring up difficult issues or ask difficult questions?

I was recently asked by two different people, one a man and the other a woman, what is the most appropriate way to bring up difficult issues or questions.

My general rule is that you do not give the best of you to those who don’t invest in you. Thus, you do not share sensitive and personal issues, problems, or past experiences until you have dated someone at least six weeks. They simply have not invested enough in you to value, appreciate, and respect what you may share. Not only does too much information too soon increase boredom, it also increases discomfort and pressure and can change the other person’s perception of you because they have not yet discovered more about you.

Furthermore, most relationships don’t make it six weeks. If you share deeply personal information too soon you increase the risk of new relationships ending before the sixth week (due to the added discomfort and pressure of your disclosure), but now you also have to worry about all the personal things they know about you.

Relative to when you should ask personal questions, there are vast differences between men and women on this issue. Most men believe that it is not relevant or necessary to tell a woman the details about their past, especially regarding anything they may feel shame about (such as past sexual indiscretions; pornography; drug, alcohol, or prescription abuse; violent behavior; etc.). A woman, by contrast, feels that this information is absolutely necessary, both for her safety and security (so she knows what she might face in the future) and for her to feel that she really knows him. Emotional intimacy and connection is her goal, and only through deep personal sharing does she feel truly connected. If a man holds things back, not only does she feel less connected to him, she often feels deceived. Furthermore, women always end up finding out eventually, and if the truth doesn’t come from him first, she can often not forgive and get over it.

Men will argue that they don’t see the point in telling a woman everything. They want her to simply trust (which is a man’s number-one need) that they have things under control. Furthermore, they really do not want to revisit their shame. They fear that she will reject, belittle, or demean them when they are vulnerable, and they want to believe that if they have been forgiven the sin or misdeed is forgotten. This belief is often perpetuated by male church leaders who, like these men, believe that the Atonement should make them clean and that the past is therefore less relevant. Although I agree with the power of the Atonement, women think very differently about the past than men do.

Understanding the past is a tool to truly understanding the individual. It matters to a woman and she wants to be included in it. If he has nothing to hide, why not share it? If he has repented and changed his life, why not trust her with the information and believe that she will see him for who he has become and value him all the more? These questions and philosophies reflect the thinking of most women. And, contrary to his fear,  most emotionally mature women will not throw his shame in his face later in a fight or otherwise (at least not on purpose). She just wants him to share with her so they can be close and so she can feel confident about the facts rather than worry about the unknown. The number-one need of a woman is to feel safe and secure and, if she discovers secrets, partial truths, lies, or painful facts later or from someone else, her ability to trust can be devastatingly impaired. A woman would much rather have a man be straightforward and direct about his misdeeds than to have him “save” her from the truth. She can get over the facts (and respect him for his honesty) much easier than she can recover from a lie.

So, to Listen So They Will Talk and Talk So They Will Listen, click here and follow the five recommended steps provided therein. Then, when you have difficult questions to ask or answer, be sure that you:


  1. Express your faith and trust in him and in the goodness of his intentions.
  2. Explain that you have a few difficult questions to ask, then find out when would be a good time for him to discuss them (so he doesn’t feel cornered right then and there).
  3. Explain how and in what way sharing the information will help you.
  4. Act curious and respectful as you ask specific questions, such as, “How old were you when you first saw pornography?” “When did you first realize that the situation was getting out of control?” “What did you do next?” Such specific questions will elicit more information, make you appear more curious, and will seem more respectful than global questions like “Have you ever had a pornography problem (sexual addiction, drug or alcohol addiction, attraction to men, etc.)?” Most men will say no to these questions because it’s inherent for men to believe that they have their behaviors under control (i.e., they may say to themselves, “I don’t have a pornography problem because I only look at it once a week”). However, they won’t hesitate to answer direct, specific, and respectful questions which, in turn, means you get more details and facts.
  5. Help him to feel valued and appreciated by touching him periodically and stating, “I can’t tell you how much it means to me that you are willing to share this with me.” Even though men are reluctant to share personal and shameful experiences, most men will share if they think it will help you or them and if they feel your warmth and respect during the conversation.
  6. Refrain from making immediate judgments or expressing sadness, anger, or disgust. Wait until later to add up what you know and to decide if you can respect the way he resolved the issue. For now just express your appreciation and respect for the fact that he’s willing to be honest.
  7. Tell him that you will only share this information with those few people you really trust and who you know will keep it private (if you feel you need to share it at all).
  8. Do not ever use any vulnerable and shameful experiences he has shared with you to hurt or humiliate him later. Men want to feel safe and secure in relationships too. Showing respect when he is vulnerable is one of the best ways to deepen a relationship, which is a major reason why women want men to be open and honest. When a man can actually feel and experience the benefits of being honest and loved in spite of his imperfections, he will begin to see and believe that his sharing really is better for them both.


  1. When she asks questions, even if she does it in a way that makes you feel attacked, state, “I would be glad to discuss that with you. I don’t have anything to hide. I will be honest with you, but I need to know that you will be respectful with what I share.”
  2. Answer her questions directly while making eye contact and keeping your chin forward.
  3. Remind yourself that your past does not define your value. Believe that what matters most is not your weaknesses but how you have addressed and resolved those weaknesses. If you have a pattern of taking action, being responsible, or overcoming your issues, then point out your efforts and trust that God will help her to see the truth and the maturity with which you’ve addressed such problems.
  4. Ask her questions as well. You’ll feel much more comfortable with being vulnerable and sharing your past and the mistakes you’ve made if she’s doing the same.
  5. Don’t expect her to make immediate decisions about what you’ve shared. Instead, state that you have faith that she will see who you are as separate from your mistakes and that you are happy to keep answering her questions.
  6. Use these opportunities to really discover who she is. As uncomfortable is it may be to show vulnerability, weakness, or shame, you can not discover who she really is and how she will really treat you in marriage without seeing how she handles these kinds of issues when dating. If she treats you with respect, sees your value, and recognizes your efforts to be honest and responsible in how you handle things, then you will know it’s safe and wise to move forward with more commitment. Sharing and being emotionally vulnerable will end up being a powerful growing experience that draws the two of you closer rather than being a bad experience. Furthermore, knowing that you have nothing to hide and nothing for her to discover later that could cause her pain or insecurity will be an additional boost to your confidence and peace of mind.


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2 thoughts on “When is the best time and way to bring up difficult issues or ask difficult questions?

  • Alisa,

    Thank you for the article it is good to know how the opposite sex approaches these issues. I had a question about this. Should men ask for the same disclosure? Since men don’t need to feel safe and secure with their partner only that they are trusted and are their hero. Does this information provide any benefit for men since we don’t derive safety or security from being trusted with those personal past details. The trust is often outweighed by the burden men feel with not being able to fix or rectify those issues. For example if a female shared she was molested, had an eating disorder or mental health issues, while I appreciate the trust shared, the burden of not being able to have protected her (feeling like a hero) often is greater than the trust especially when we know that she has trusted many of her closest friends with the issues. I know she will feel more safe and secure with us in sharing the information, but should we ask for it or let her share it when she is ready?

    • James,

      If you don’t show an interest in her past she will not develop a deeper emotional bond to you and lose interest and trust in you. This is particularly the case between the fourth and sixth week. Thus, it is critical that you develop more emotional and personal sharing during this time.

      I suggest you simply get her talking about her past (good memories, sad memories, hopes, dreams, fears), and then if she brings up something heavy on her own say, “I am glad you could share that with me. I don’t need to pry, what ever you want to share I am happy to listen to.”

      Then if she begins to get into gruesome details or the conversation lingers for a really long time, say “As a guy when there is nothing I can do to help it makes me feel bad. Please tell me what kind of things I can do to help (i.e. support you in going to counseling, give you hug, offer advice, just listen), but please know if I can’t fix it in some way it will really bum me out. I don’t want to see you unhappy or hurting.”

      I hope this helps. It’s a catch twenty-two. If you don’t make it easier for her to talk about she won’t feel connected; if you listen to too much it stresses you out. However, such is the struggle of men and women. I trust you will find a way to balance this.

      OH! AND AS A WARNING – It really is in your best interest to know details about her past. I promise you a woman with a really bad past, either through abuse or out of control behaviors will have issues that will come up later and will need to be address. Some of her issues may even be so problematic that you will find a long-term relationship with her is terribly difficult. Not knowing her past will not shield you from this fact. If you discover a lot of issues, you need to see what she has actively done to resolve them and then seek counseling so you can know more about the issues and how they might affect you. Perhaps the reason you have felt so burdened in the past by a woman’s issues is because she was not actively working on and resolving the issue so you felt even worse. This would have been a warning sign of big issues later because of her passive investment in her problems and likelihood that acting-out behaviors may result down the road.

      I hope this helps.


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