101 Questions to Ask Before You Get Engaged

Sarah thought she knew everything about her boyfriend of two years until their first major argument revealed a completely different person. Mark seemed perfect during their romantic dinners and weekend getaways, but when life got real, she discovered they had fundamentally different values about money, family, and faith. This scenario plays out countless times across the globe as couples rush into engagement without truly knowing their partner.

The excitement of falling in love can blind us to crucial compatibility factors that determine long-term relationship success. While butterflies and romance are wonderful, they cannot sustain a marriage through decades of real-life challenges. The questions you ask before engagement are not romantic killers but relationship builders. They serve as a bridge between infatuation and informed commitment, helping you discover whether your love story has the foundation to become a lifelong partnership filled with growth, understanding, and genuine intimacy.

Understanding relationship red flags before engagement can save you years of heartache and disappointment. A red flag is any behavior, attitude, or pattern that signals potential problems in a long-term commitment. These warning signs often appear subtle during the dating phase but become magnified in marriage.

Consider the story of Jennifer, who ignored her fiancé David's controlling tendencies because she interpreted them as protective love. During their engagement, David gradually began dictating her clothing choices, questioning her friendships, and monitoring her social media activity. What Jennifer initially saw as devotion was actually the beginning of emotional abuse. She later realized that his need to control stemmed from deep insecurity and trust issues that predated their relationship.

The most dangerous red flags include any form of physical or emotional abuse, addiction issues without active recovery, financial irresponsibility, inability to maintain healthy relationships with family and friends, and patterns of deception or dishonesty. Other warning signs include someone who refuses to discuss the future, shows extreme jealousy, has unresolved anger issues, or demonstrates a complete lack of spiritual depth or growth.

Pay attention to how your partner treats service workers, handles stress, responds to criticism, and interacts with their family. These behaviors reveal character more clearly than romantic gestures. If you find yourself making excuses for their behavior or believing you can change them after marriage, step back and reassess. Marriage amplifies existing patterns rather than transforming them.

Trust your instincts and listen to concerns from trusted friends and family members. If multiple people express worry about your relationship, consider their perspective seriously. Remember that choosing to end an engagement, while painful, is far less devastating than divorce. Your future self will thank you for having the courage to address these red flags now rather than hoping they disappear after the wedding.

Character emerges through life's challenges and everyday choices, making it essential to explore your partner's values, responses, and personal history before making a lifetime commitment. Deep questions serve as windows into the soul, revealing patterns that surface conversations never uncover.

Wright shares the example of Tom and Lisa, whose surface compatibility masked fundamental differences in character. During their engagement preparation, they discovered that Tom's definition of honesty included withholding information to avoid conflict, while Lisa valued complete transparency. This revelation led to important conversations about trust, communication styles, and their expectations for marriage. By addressing these differences early, they developed strategies for building genuine intimacy rather than discovering incompatibility after their wedding.

Begin by exploring spiritual foundations through questions about faith journeys, relationship with God, and moral decision-making processes. Ask about family relationships, particularly how they handle conflict with parents and siblings. Investigate their response to failure, disappointment, and criticism. Discover their understanding of forgiveness, both giving and receiving it. Explore their relationship with money, work ethics, and future dreams.

Character-revealing questions might include asking about their greatest regrets and what they learned from them, describing how they handle stress and anger, or explaining their process for making important decisions. Ask about their friendships, what qualities they value in others, and how they maintain long-term relationships. Explore their views on commitment, sacrifice, and what they believe makes marriages successful.

The key to these conversations lies not just in the answers but in how they respond to the questioning process itself. Do they welcome deep discussions or resist vulnerability? Are they defensive about their past or open to growth? Their willingness to engage authentically in these conversations often predicts their capacity for emotional intimacy in marriage.

Spiritual and emotional compatibility form the bedrock of lasting marriages, creating connection that transcends physical attraction and shared interests. These dimensions of relationship require intentional cultivation and honest assessment before engagement.

The book describes Michael and Rachel, whose similar church attendance masked significant spiritual differences. While both attended services regularly, their personal relationships with God varied dramatically. Michael viewed faith as a cultural tradition and social activity, while Rachel sought to integrate biblical principles into daily decisions and personal growth. Through honest conversations about prayer, Scripture study, and spiritual goals, they discovered this gap and worked together to align their spiritual journeys before marriage.

Emotional compatibility involves understanding each other's emotional languages, processing styles, and needs for connection. Some people express love through words of affirmation, while others demonstrate care through acts of service or physical touch. Some need extensive verbal processing to work through problems, while others prefer quiet reflection time before discussing issues.

Assess your spiritual compatibility by discussing personal relationships with Christ, prayer habits, church involvement preferences, and views on biblical marriage roles. Explore how faith influences daily decisions, financial choices, and future family planning. Share spiritual highs and lows, discussing what draws you closer to God and what creates distance in your spiritual life.

Build emotional compatibility by practicing vulnerability in safe conversations. Share fears, dreams, and past hurts while observing how your partner responds. Notice whether they offer comfort, advice, or simply listen based on your needs. Discuss how you each handle conflict, process disappointment, and celebrate victories. Practice praying together regularly, as spiritual intimacy often unlocks emotional connection.

Remember that compatibility does not mean uniformity. Healthy relationships include differences that complement rather than compete. The goal is understanding and supporting each other's spiritual and emotional needs while growing together toward greater maturity and intimacy.

Successful marriages require aligned visions for the future, shared values, and compatible life goals. While opposites may attract, fundamental differences in core values and future aspirations often create insurmountable challenges in marriage.

Wright illustrates this through Kevin and Amanda's story. Kevin dreamed of traveling the world, starting his own business, and having minimal family obligations, while Amanda envisioned a stable home, close extended family relationships, and traditional family structure with multiple children. Initially, they assumed love would resolve these differences, but deeper conversations revealed incompatible life visions that required serious negotiation and compromise before they could consider marriage.

Begin planning your future by discussing career aspirations, financial goals, and lifestyle preferences. Explore your views on children, including how many you want, parenting philosophies, and educational priorities. Discuss extended family relationships, including care for aging parents and holiday traditions. Address geographic preferences, housing goals, and community involvement desires.

Examine your values around money, work-life balance, service to others, and personal growth. Discuss how you plan to maintain individual identities while building a shared life together. Explore your expectations for friendship maintenance, hobby pursuits, and personal development after marriage. Consider your views on retirement, legacy building, and what you hope to accomplish together.

Create specific timelines for major life goals, discussing when you might buy a house, start a family, change careers, or pursue further education. Be honest about non-negotiable values and flexible areas where compromise is possible. Identify potential obstacles to your dreams and develop strategies for overcoming them together.

Remember that life rarely follows exact plans, so discuss how you handle unexpected changes, disappointments, and new opportunities. The goal is not perfect alignment but rather compatible values and shared commitment to building a life that honors both your individual callings and your partnership.

Second marriages carry unique challenges and opportunities that require additional preparation and honest assessment. Previous marriage experience brings both wisdom and baggage that must be carefully navigated before making another lifetime commitment.

The author presents the case of Robert and Susan, both previously married, who initially focused on their strong attraction and compatibility while avoiding difficult conversations about their first marriages. Eventually, they realized that understanding their previous relationship patterns, unresolved grief, and lessons learned was essential for building a healthy second marriage. Through careful examination of their first marriages, they identified personal growth areas and developed strategies for avoiding previous mistakes.

Second marriages face higher divorce rates partly because people often repeat previous patterns without addressing underlying issues. Begin by thoroughly examining your first marriage, identifying what went wrong, your personal contributions to problems, and specific changes you have made since divorce. Assess your recovery process, including whether you have grieved the loss of your first marriage and dealt with any anger, bitterness, or trust issues.

Consider the impact of children from previous relationships, including custody arrangements, financial obligations, and blending family dynamics. Discuss relationships with ex-spouses, boundary setting, and how to prioritize your new marriage while maintaining healthy co-parenting relationships. Address financial complications, including debt, support payments, and combining financial resources.

Evaluate whether sufficient time has passed since your divorce to allow for emotional healing and personal growth. Most experts recommend at least two to three years between divorce and remarriage to ensure adequate recovery. Assess your motivations for remarrying, ensuring they stem from healthy desires for companionship rather than fear of loneliness, financial need, or rebound reactions.

Seek pre-marital counseling specifically designed for second marriages, which addresses unique challenges like trust rebuilding, family blending, and managing complex relationships. Consider attending divorce recovery programs or support groups to ensure you have processed your previous marriage experience completely. Your second marriage deserves the benefit of all the wisdom and healing you can bring to it.

Building a marriage that lasts requires courage to ask difficult questions, wisdom to address differences honestly, and commitment to grow together through challenges. This comprehensive approach to pre-engagement preparation transforms surface-level attraction into deep, lasting love built on understanding, compatibility, and shared vision. As the author emphasizes, "The greater the amount of information you have, the better you'll be able to make a good decision."

The investment you make in thoroughly knowing your potential spouse before engagement pays dividends throughout your marriage. These conversations, while sometimes uncomfortable, build the foundation for lifetime intimacy, trust, and partnership. They help you move beyond infatuation into the kind of mature love that weathers life's storms and celebrates its joys together.

Start today by choosing three questions that resonate most strongly with your current relationship situation. Schedule dedicated time with your partner to explore these areas deeply, approaching the conversations with curiosity rather than judgment. Remember that the goal is not perfection but rather informed commitment based on genuine knowledge and acceptance of each other. Your future marriage will be strengthened by every honest conversation you have now.