101 Questions to Ask Before You Get Engaged
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Read between September 17 - September 18, 2023
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1. What makes it easy for you to be open and vulnerable, and what makes it difficult? The answers to these questions are a road map. First, can your partner be vulnerable? Have you seen signs that they can? You want to respond in a way that makes them feel at ease in your presence and not do anything to put a roadblock in their way. Give them every opportunity. Perhaps this is the first safe relationship they’ve experienced. If vulnerability and openness can’t occur here, how can it occur in marriage?
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4. Describe how you were disciplined as a child. If you have children, how will your discipline be the same and how will it be different than what you experienced? Are there major differences in discipline styles between you and your partner? Would you be comfortable with their background and what they intend to do? Even though many say, “I’ll never discipline my children as I was disciplined,” we often revert to the way we were raised. Expect to see some patterns repeated unless definite steps are taken to bring about change. How much involvement have each of you had with children? What books ...more
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9. We hear a lot today about compatibility. What does this mean to you? Compatibility means being capable of living together harmoniously, or getting along well together. It means to be in agreement, to combine well. It also means blending together so a relationship enhances, instead of interferes with, each partner’s capabilities. A couple needs to work on compatibility in all areas of their relationship. Those who become compatible have certain characteristics or skills that help them develop compatibility: They flex, stretch, adapt, and change. There’s no other way.
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17. What are the questions about me you’ve always wanted to ask but never have? This could become very personal. That’s good. You may be surprised. Above all, don’t be defensive or offended. Thank your partner for asking. You may want to answer immediately or reflect on the questions for a while. And another thought—why haven’t these questions been asked before? Is it because your partner tends to be hesitant or reserved, or because they sense it would not be received well? That’s something to think about.
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22. If I were a doctor and you were describing your medical history for me, what would it entail? (Accidents, hospitalizations, diseases of any kind including HIV/AIDS, syphilis, herpes, or others.) Some individuals have been shocked to learn this information after they’re married. That’s when you feel deceived. Some conditions could limit having children or where you live. Everyone’s imperfect physically. Learn about it now. Many people marry knowing about their partner’s limitations and accept them fully.
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23. If something really bothered you about me, how would you go about expressing it to me? The way we express our concerns to one another is the issue. Delivery is everything. If you feel attacked, you’ll probably be defensive. Some tend to bottle up their feelings and concerns, but these can accumulate, and often there is a blowup later. Proverbs gives us some guidelines:  “A man who refuses to admit his mistakes can never be successful. But if he confesses and forsakes them, he gets another chance” (Proverbs 28:13 TLB).  “A word fitly spoken and in due season is like apples of gold in a ...more
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27. How would you keep romance alive if you were to marry? What appears to be romantic to one person might not be to another. Your partner may have several ideas, but they may not light your fire. It’s important to discover what type of romance each of you enjoys—that will give you a good road map for keeping the flame alive. And by the way, it won’t just happen. There needs to be a commitment to make it happen. And it helps to look your partner in the eye and say “I love you” every day.
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28. What are five habits you’re glad you have and five you wish you didn’t? Everyone has some habits or patterns. Are yours the same or similar? How do you feel about your partner’s? Can you live with them? Accept them? Do they want you to help “get rid of the ones they don’t like?” Habits you find annoying now will only be intensified after marriage.
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33. 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? Illness is not something you think about before marriage. Everyone has a pattern of response they’ve developed over the years, as well as a mixture of expectations and needs when they’re sick. Many conflicts have occurred because of not discussing this in advance. One or both of you may need to change your way of responding in order to meet the other’s needs.
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35. What are the “must have” and “must not have” qualities in a person you may want to spend the rest of your life with? Listen carefully. Can you match this list with who you are and what you have to offer? It’s essential to clarify these in advance because these qualities won’t change easily and could become demands. Sometimes “shopping lists” are reasonable. Sometimes they’re not.
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49. What is your dream or fantasy of a “perfect marriage”? A person’s fantasy can be shaped by what they’ve seen in real life, film, books, and so on. There is no perfect marriage because there are no perfect people. A marriage is an unconditional commitment of two imperfect people. It’s better to talk about a realistic marriage. Why not interview several couples on the subject of what makes their marriage work and benefit from their experience?
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50. What are three ways in which you see us as different? What are three ways in which you see us as similar? Which of these are you most comfortable with? Couples are drawn together by differences as well as similarities. Sometimes we respond to differences because they fill our empty places. Sometimes we’re comfortable with similarities. You may look at one another’s differences now and say, “Oh, you’re so unique!” After a couple years of marriage you may say, “I knew you were different—but not this much!” You may see their differences as wrong and set out on a crusade to make the other ...more
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51. What qualities do you see in your parents that you expect to see in your future spouse? Most of us have subtle unexpressed expectations that what is positive in our parents will stay with us forever because our spouse is likely to have the same traits or qualities. That can put a huge burden on your partner. Identify those qualities and evaluate your expectations. And speaking of parents, observe the way your partner treats their parent of the opposite sex. It’s often a preview of what you can expect.
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54. How comfortable are you with confrontation or conflict? How do you usually resolve conflicts? One of you may be accustomed to confrontation, and for the other, it’s new. It may be second nature and a positive experience in your relationship, or a sign that it is in trouble. Perhaps you have wanted to discuss this but have been afraid to move in that direction. Talk about it. Where does anger enter into this issue? Anger expressed in a healthy, nonattacking way can build a relationship. Repressed or constantly held-in anger will eventually damage the person and the relationship.
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59. What is your idea of a “family”? What would you change about your family and how you were raised? What steps would you take to make these changes? The more you know about your partner’s family, the greater the insight you will have regarding their attitudes and beliefs about family. You’ll discover why they have certain concerns, what their likes and dislikes are, and why they need from you what they do. We are shaped by our families but we may not want to re-create them. That’s why you need a specific plan to follow to make those changes in your new family. Otherwise, you continue what ...more
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60. What are your financial responsibilities and goals? How capable are you in budgeting, balancing checkbooks, shopping patterns? How stressful are these things to you? What debts do you have at this time, and have you ever filed for bankruptcy? Finances are at the heart of so many conflicts in relationships. Each of you needs to know what one another earns as well as future potential. Have each of you used a budget? If not, begin working on it now if you proceed in your relationship. Is shopping a planned activity with financial resources in mind or is it a credit-card binge? Is shopping a ...more
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85. How well do you handle constructive criticism and advice? Take a moment and observe how your partner responds to this question. Do they welcome instruction and advice? Or, do they know everything already? Find out how they would like to be approached if you felt advice could be helpful. Also, ask who they are the most open to receiving advice from. If they answer “Anyone but you,” watch out!
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86. If marriage is on the horizon, are you planning to go through premarital counseling? After you’re married, would you be open to seek marriage counseling if major concerns arise? If a partner says, “I don’t need any help—I know what I need to know,” watch out! Everyone needs to be open to as much help as they can receive about marriage. If your partner doesn’t want premarital counseling, what makes you think they would seek help after marriage?
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88. Of all the emotions we experience in life, what are the easiest ones for you to express and what are the most difficult? Everyone is an emotional being. Some experience or express emotions more intensely than others. Some children are raised without an emotional or feeling vocabulary, so it is difficult for them as adults to express what they are experiencing inside. Talk about each of the following: fear, worry, anxiety, depression, sadness, anger, rage, frustration, guilt, shame, delight, sorrow, joy. (This will keep you busy for a while.)
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92. Do you feel you need to compromise or sacrifice anything to be a part of this relationship? Relationships are based on give and take. They can’t consist of all taking and no giving, or all giving and no taking. Balance is key. Make sure you learn what strikes a balance in the give-and-take arena for the both of you. Be wary if your partner feels their life is one giant compromise.
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93. What are the five biggest fears in your life? This can be a very revealing question. Couples can be married for years and never be aware their partner has any fears. How do these fears affect your relationship? How could you assist one another in overcoming these fears?
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99. Do you believe you and I should be honest about everything in our relationship, or should some things be kept private? If I asked your past partners if you were honest and trustworthy, how would they answer? Sometimes people let things slide during courtship in order to not rock the boat. They may even think they’ll sway you after you’re married. It won’t work. You need a person who is truthful and doesn’t bend the truth in any way. You need a partner who is honest with themselves and doesn’t practice self-deception. You need a person who is honest with you.