101 Questions to Ask Before You Get Engaged

101 Questions to Ask Before You Get Engaged Plot Summary

Introduction

When we fall in love, our hearts often race ahead of our minds. That magical feeling of finding "the one" can cloud our judgment and lead us to make life-altering decisions without proper examination. Yet, building a lifelong partnership requires more than romantic feelings—it demands intentional investigation, honest communication, and careful evaluation of compatibility. The path to a wise engagement means asking hard questions now rather than facing painful revelations after saying "I do." Many relationships falter because couples marry strangers—people they thought they knew but didn't truly understand. This exploration guides you through essential questions and conversations designed to remove the mystery and build authentic knowledge of your potential life partner. By examining values, confronting potential red flags, and establishing healthy communication patterns before engagement, you create a solid foundation that can support a lifetime of love, growth, and partnership.

Chapter 1: Know Your Partner, Not a Stranger

Marrying a stranger is perhaps the most common yet devastating mistake couples make. As counselors often hear: "The person I married was not the same one I honeymooned with. It's as though they changed overnight." This disconnect happens when couples skip the crucial process of deep acquaintanceship—a combination of how well you know your partner and how long you've experienced life together before marriage. Consider the story of a man who shared his dating experience after six months with a woman he initially found attractive. Despite enjoying common interests, he found himself "talking himself into" continuing the relationship from the very first date. There was something missing he couldn't identify until months later—common sense and sensitivity to his needs. As he reflected, he realized his subconscious had evaluated the relationship accurately on the first date, but he ignored those instincts, spending six irretrievable months hoping things would improve. This gentleman learned a valuable lesson: if you have to talk yourself into continuing a relationship after initial dates, it likely won't work in the long run. Just as you wouldn't purchase a car without asking questions about its performance, warranty, and history, you shouldn't proceed toward engagement without thoroughly examining the person you're considering spending your life with. The acquaintanceship process requires both depth of knowledge and breadth of experiences. This means not only having deep conversations but also experiencing various situations together—observing how your partner handles stress, interacts with friends and family, resolves conflicts, and demonstrates values through everyday decisions. The longer and better you know someone before marriage, the greater your chances of marital satisfaction. Approach your relationship with courage to ask difficult questions, even when answers might be uncomfortable or unromantic. Remember, you will discover these answers eventually—the only question is whether you'll learn them before or after making a lifelong commitment. Gathering information now helps you make a good decision, potentially saving you from heartache or confirming you're heading in the right direction.

Chapter 2: Ask the Hard Questions Now

Asking difficult questions before engagement might feel uncomfortable or unromantic, but these conversations are crucial investments in your future happiness. When couples avoid tough topics during courtship, they often discover shocking incompatibilities after marriage when problems are much harder to resolve. Addressing potential issues now gives you the freedom to make informed decisions while you still have options. Jeffrey Larson, in his book "Should We Stay Together?" emphasizes the importance of thorough acquaintanceship before marriage. He explains that true acquaintanceship combines depth of knowledge with breadth of experiences. The connection between acquaintanceship and marital satisfaction is straightforward: the longer and better you know someone before marriage, the more likely you are to have a satisfying marriage. This happens because extended acquaintanceship allows you to understand not only your partner's personality but also your strengths and weaknesses as a couple. One individual shared how he initially dismissed red flags in relationships, hoping issues would resolve themselves. Now in his 40s, he realizes he didn't even know what questions to ask in his 20s and 30s. His advice: ask questions and store the answers to check for consistency between words and actions. If something appears to be a red flag, confront it immediately rather than dismissing it. Interact with your partner's friends in group settings, spend time with their parents, and observe how they handle pressure situations to gain insight into their character. When approaching difficult conversations, create a safe environment where both people can be vulnerable. Start by sharing your own thoughts and feelings, then listen with genuine interest to your partner's perspective without judgment. Remember that these conversations aren't about finding perfect answers but about determining compatibility and establishing communication patterns that will serve you throughout your relationship. If your partner avoids certain topics or becomes defensive, consider this valuable information about how conflicts might be handled in marriage. A partner who can engage thoughtfully with difficult questions now will likely approach marital challenges with the same maturity in the future. Conversely, avoidance patterns tend to persist and intensify over time. The questions you ask now can help you identify potential issues, establish healthy boundaries, and build a foundation of mutual understanding that will sustain your relationship through future challenges. Immediate discomfort is a small price to pay for long-term relationship success.

Chapter 3: Examine Your Values and Compatibility

Compatibility goes far beyond enjoying the same movies or restaurants—it reaches into your core values, life goals, and approaches to important issues. True compatibility means being capable of living together harmoniously, combining well, and enhancing rather than interfering with each other's capabilities. Couples who build lasting relationships have developed skills to flex, stretch, adapt, and change together through life's challenges. A revealing example comes from a man who described his struggle with values compatibility. He had grown up in a family that practiced careful financial stewardship, saving diligently and avoiding debt. When dating a woman from a family that viewed credit as a lifestyle tool, with maxed-out cards and frequent financial crises, he initially dismissed these differences as minor issues that love would overcome. Only after becoming engaged did he realize the depth of their incompatibility when she suggested opening joint accounts and credit cards, putting his financial security at risk. Their different values about money reflected broader differences in responsibility, planning, and risk tolerance. Value alignment must extend to spiritual beliefs, family priorities, and life goals. The book suggests exploring specific areas like discipline styles for future children, attitudes toward work-life balance, and expectations about family relationships. These discussions reveal whether you're building on similar foundations or trying to merge fundamentally different worldviews. To effectively examine compatibility, create dedicated time for focused conversations without distractions. Ask open-ended questions about your partner's upbringing, influences, and how these shaped their current values. Share your own background and listen for areas of alignment and potential conflict. Observe how your partner handles differences—do they respect perspectives that differ from their own or dismiss them? The way you navigate these discussions often predicts how you'll handle more significant challenges in marriage. While no couple agrees on everything, successful partnerships build on substantial common ground in core values while respecting differences in preferences and approaches. The goal isn't finding someone identical to you but someone whose values complement and strengthen yours, creating a relationship that helps both partners grow. Remember that partial compatibility doesn't work well—it creates holes in the relationship that widen under pressure. Spend time now determining whether your fundamental values align, as these aspects of personality rarely change significantly after marriage.

Chapter 4: Discover Your Emotional and Spiritual Alignment

Emotional and spiritual alignment forms the bedrock of lasting relationships. This alignment isn't about identical personalities or religious expressions, but rather compatible approaches to emotional expression, spiritual growth, and life's deeper questions. When couples connect on these fundamental levels, they build resilience that helps them weather life's inevitable challenges. Dr. Paul Tournier, a renowned psychiatrist, observed that "It is only when a husband and wife pray together before God that they find the secret of true harmony, that the difference in their temperaments, their ideas, and their tastes enriches their home instead of endangering it." One couple in the book exemplified this principle. After dating for months, they struggled with communication until they began praying together regularly. Initially uncomfortable with spiritual vulnerability, they started with simple prayers before meals, eventually growing into deeper spiritual conversations that transformed their relationship. This practice opened channels of communication that had previously been closed, allowing them to address issues they had avoided. Emotional alignment involves understanding and respecting each other's emotional landscapes. This includes recognizing how you each express and process emotions like anger, sadness, joy, and fear. Some partners might be highly expressive while others process emotions internally. Neither approach is inherently wrong, but mismatched expectations about emotional expression can create significant relationship strain. To explore your emotional and spiritual alignment, ask questions like: "What makes it easy or difficult for you to be open and vulnerable?" "Describe your spiritual journey over the past ten years, including high and low points," and "How has your relationship with Jesus Christ changed since this current relationship?" These conversations reveal not just current spiritual practices but the trajectory of spiritual growth and how your relationship influences that journey. Create opportunities to experience spiritual activities together—attend worship services, read devotionals, volunteer for service projects, or have theological discussions. These shared experiences reveal how compatible your approaches to faith might be in marriage and whether spiritual activities bring you closer together or create tension. Pay attention to how comfortable you feel discussing spiritual matters and praying together. If prayer and spiritual conversation flow naturally between you, this often indicates healthy spiritual alignment. However, if these activities feel forced or create anxiety, explore why these barriers exist and whether they can be overcome through understanding and patience. Remember that spiritual alignment doesn't mean identical faith expressions but complementary approaches that strengthen rather than undermine each other's spiritual growth.

Chapter 5: Address Potential Red Flags With Courage

Identifying and addressing red flags requires both awareness and courage. These warning signs aren't always dramatic—they can be subtle patterns that indicate deeper incompatibilities or issues that may threaten relationship health over time. Ignoring these warnings might feel easier in the moment, but confronting them honestly is an act of love toward yourself and your partner. The experience of one woman illustrates the importance of heeding warning signs. She was turning thirty and felt pressured by her "biological clock," which she described as "flashing so brightly that it blinded me from all the signs." Despite her partner's controlling behavior, emotional distance, and unwillingness to discuss important topics, she proceeded toward engagement, convincing herself things would improve after marriage. Within a year of their wedding, his controlling tendencies escalated to emotional abuse, and they separated. Looking back, she acknowledged that all the warning signs had been present during dating, but she had chosen to ignore them rather than address them directly. Common red flags include patterns of dishonesty, inability to resolve conflicts, addiction issues without recovery programs, significant financial problems, controlling behaviors, and emotional or physical abuse. These issues rarely improve with marriage and often worsen under the pressure of deeper commitment. Additionally, warning signs might include relationships characterized by constant quarreling, unrealistic expectations about changing your partner, or the sense that you must compromise core aspects of yourself to maintain the relationship. When you notice potential red flags, approach the conversation with care rather than accusation. Use "I" statements to express your concerns: "I've noticed this pattern, and I'm concerned about what it might mean for our future together." Listen carefully to your partner's response—defensiveness, dismissal, or unwillingness to discuss the issue often confirms the presence of a problem, while openness to examining the concern together can be reassuring. Remember that addressing red flags isn't about finding perfection but about determining whether issues can be resolved in healthy ways. Some challenges can be worked through with counseling, clear communication, and mutual commitment to growth. Others, particularly those involving abuse, addictions without treatment, or fundamental value differences, may indicate that proceeding toward marriage would be unwise. Trust your instincts when they signal concern. If you find yourself frequently making excuses for your partner's behavior or feeling you must hide aspects of your relationship from friends and family, these are important internal warnings to heed. As one person advised, "If that inner voice tells you that you are making a mistake, at least stop and listen to it."

Chapter 6: Build Communication Patterns That Last

Communication is the lifeblood of healthy relationships—not just what you say, but how you say it and how well you listen. The patterns of communication you establish before marriage tend to persist and intensify afterward, making it crucial to develop healthy interaction styles early in your relationship. One couple described in the book illustrates the importance of establishing good communication patterns. During their dating relationship, Michael and Sarah seemed perfectly compatible until they encountered their first major disagreement about career priorities. Michael immediately became defensive and withdrew, while Sarah became increasingly critical and pursuing. This cycle continued until a counselor helped them recognize their destructive pattern. They learned that Michael had grown up in a family where conflict meant rejection, so he protected himself by withdrawing. Sarah, raised in a family that resolved issues through intense discussion, interpreted his withdrawal as not caring. Once they understood these patterns, they developed new approaches—Michael practiced staying engaged during difficult conversations, while Sarah learned to approach issues more gently. Effective communication requires both partners to adapt to each other's styles. Some people are expanders who provide extensive detail, while others are condensers who prefer brevity. Some are direct communicators who get straight to the point, while others are indirect communicators who approach topics gradually. Neither style is inherently better, but couples must learn to "speak each other's language" to avoid frustration and misunderstanding. To build lasting communication patterns, practice active listening—focusing completely on understanding your partner rather than formulating your response. Paraphrase what you've heard to confirm understanding before responding. Create regular opportunities for meaningful conversation without distractions from phones, television, or other interruptions. Establish a habit of daily check-ins to share thoughts, feelings, and experiences. When conflicts arise, approach them as opportunities for growth rather than battles to be won. Work toward resolving issues instead of merely compromising or one person always yielding. As noted in the book, healthy conflict resolution isn't about determining who's right but finding solutions that meet both partners' needs and strengthen the relationship. Remember that communication encompasses more than words—body language, tone, and timing all influence how messages are received. Be mindful of these elements, especially during difficult conversations. As Proverbs 25:11 notes, "A word fitly spoken and in due season is like apples of gold in a setting of silver." Timing and delivery can make the difference between a conversation that builds connection and one that creates distance.

Chapter 7: Prepare for Lifelong Partnership

Preparing for lifelong partnership requires a mindset shift from dating to commitment—moving beyond the excitement of romance to the intentional work of building a lasting relationship. This preparation involves practical planning, emotional readiness, and a shared vision for your future together. A friend shared his experience of entering marriage without proper preparation. Initially, he and his wife focused primarily on planning their wedding day rather than their marriage. They assumed their strong feelings would naturally translate into a harmonious partnership. Six months after their beautiful ceremony, they were struggling with unexpected conflicts about finances, family relationships, and household responsibilities. After seeking counseling, they realized they had never discussed their expectations about these fundamental aspects of married life. Through deliberate conversations and planning, they eventually built the strong marriage they had always wanted—but they wished they had done this preparation work before their wedding rather than after painful conflicts emerged. Marriage preparation includes discussing practical matters like financial management, career plans, family planning, and division of household responsibilities. Beyond these logistics, couples must prepare emotionally by examining their expectations about marriage, understanding family-of-origin influences, and developing skills for conflict resolution and emotional intimacy. To effectively prepare, participate in comprehensive premarital counseling that addresses both practical and relational aspects of marriage. Read books on marriage together, discussing how the principles apply to your relationship. Consider taking personality assessments to better understand your differences and similarities. Develop a shared spiritual foundation through prayer, worship, and discussion of your faith journeys. Interview several couples with healthy marriages, asking what makes their relationships work and what challenges they've overcome. This provides realistic models and practical wisdom from those who have successfully navigated marriage's complexities. Seek mentorship from an older couple who can provide guidance and perspective as you prepare for and begin your marriage. Remember that preparing for marriage isn't about achieving perfection but about establishing a foundation of knowledge, skills, and shared expectations that will support your relationship through life's inevitable changes and challenges. As one happily married person advised, "A wedding is exciting but it lasts just one day. Make sure this is the person you want across the breakfast table from you every morning." The preparation you invest now directly influences the quality of your future marriage. By addressing potential issues before they become problems and developing healthy patterns of interaction, you create a relationship environment where both partners can thrive and grow together.

Summary

The journey toward marriage requires more than romantic feelings—it demands intentional preparation, honest communication, and thorough examination of compatibility. As we've explored, knowing your partner deeply before engagement, asking difficult questions, examining values alignment, discovering emotional and spiritual compatibility, addressing red flags, building lasting communication patterns, and preparing practically for partnership create a foundation for lasting love. Remember this powerful insight from the book: "A wedding is exciting but it lasts for just one day. Is this the person you want across the breakfast table from you every morning?" Your relationship deserves the investment of thoughtful preparation now, before permanent commitments are made. Begin today by selecting one area from this path to wise engagement that needs your attention, whether it's having a difficult conversation you've been avoiding or exploring deeper values compatibility. The courage you show in building proper foundations now will support the lifelong partnership you desire for tomorrow.

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H. Norman Wright

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