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101 Questions to Ask Before You Get Engaged

10 min

Introduction

Narrator: Imagine walking onto a car lot and spotting a sleek, great-looking used car. You’re immediately captivated. The salesperson approaches and starts to tell you about the warranty, the performance history, and the price, but you wave them off. "Don't bother me with the details," you say. "I'll take it. Just tell me where to sign." No one would ever make a significant financial investment this way. The idea is absurd. Yet, every year, countless people make a far more significant lifelong commitment—marriage—with even less investigation. They fall in love with the exterior and never bother to look under the hood.

This is the central, startling premise of H. Norman Wright's book, 101 Questions to Ask Before You Get Engaged. The author argues that one of the greatest risks in modern relationships is the failure to conduct due diligence, leading people to commit their lives to a virtual stranger. The book serves as a practical guide to prevent this, framing deep, intentional questioning not as a lack of romance, but as the very foundation of a lasting love.

The Peril of Marrying a Stranger

Key Insight 1

Narrator: The book begins with a sobering reality: many marital problems stem from a simple, devastating discovery that the person one married is not the person one thought they were. Wright explains that this isn't always about malicious deception. Sometimes it's due to "courtship deception," where both partners present an idealized version of themselves. Other times, it's simple naïveté or a reluctance to ask difficult questions for fear of rocking the boat. The result is the same: a union built on assumptions rather than truth.

To illustrate the folly of this approach, Wright presents the powerful analogy of buying a used car. A prospective buyer who is immediately taken by a car's appearance wants to purchase it on the spot. When the salesperson tries to offer details about its history, performance, and price, the buyer refuses to listen, insisting on the purchase without any information. The story ends with the rhetorical question of whether any sane person would act this way. The connection is clear and sharp: people often put more effort into researching a vehicle than they do into understanding the person they plan to spend their life with. Wright quotes researcher Jeffrey Larson, stating, "The longer and better you know someone before marriage, the greater the likelihood of marital satisfaction." This "acquaintanceship" isn't just about time; it's about the depth and breadth of knowledge one has about their partner's character, history, and flaws.

Don't Marry Potential, Marry Reality

Key Insight 2

Narrator: One of the most common and dangerous traps in a relationship is marrying someone for their potential. Wright identifies this as a form of self-deception where one partner sees shortcomings in the other—perhaps in their ambition, emotional stability, or financial responsibility—but believes they can "fix" or change them after the wedding. This person isn't committing to their partner as they are, but to an idealized future version of them.

The book shares a composite story of this phenomenon. A person is dating someone with clear issues but rationalizes them by focusing on their "potential." Friends and family may raise concerns, but they are dismissed. The person believes that the commitment of marriage will be the catalyst for their partner's transformation. Wright warns that this is a recipe for disaster. People cannot be fundamentally reshaped by another's will. Entering a marriage with a renovation project in mind almost always leads to frustration, resentment, and a feeling of being trapped. The partner who was supposed to change feels constantly criticized, while the "fixer" feels perpetually disappointed. The core message is unequivocal: you must love and accept the person standing before you today, with all their existing flaws, because that is the person you are marrying.

Heed the Warning Signs and Trust Your Gut

Key Insight 3

Narrator: While love can feel exhilarating, Wright cautions that feelings alone are not a reliable guide. It is crucial to pay attention to internal warning signs and external red flags. He emphasizes that if a person has to constantly convince themselves to stay in a relationship, it is likely not the right one.

This point is brought to life through the story of a man reflecting on a past relationship. He dated a "nice woman" for six months. She was attractive and they shared some interests, but from the very beginning, something felt off. He found himself having to talk himself into going on a second date, and then a third. He ignored his initial gut feeling because, on paper, everything seemed fine. Six months later, he finally admitted to himself that he was settling and had been ignoring his instincts all along. He realized a profound truth, which Wright echoes: "If you have to talk yourself into buying something, you probably won’t use it... if I have to talk myself into a second or third date, it probably won’t work either in the long run." This principle extends to engagement. Wright quotes another source, stating, "If you have mixed feelings about engagement, don’t! You need to be certain." These feelings are not random doubts; they are often our intuition signaling that a deeper incompatibility exists.

The Unique Calculus of a Second Marriage

Key Insight 4

Narrator: For those who have been married before, the stakes are different and often higher. The book dedicates a specific section to this reality, acknowledging that while a second marriage can be wonderfully redemptive, it comes with its own unique set of challenges. Wright argues that it is essential for those considering remarriage to be brutally honest about their past and have realistic expectations for the future.

The story of Sarah, a woman preparing for her second marriage, illustrates this beautifully. Her first marriage to Mark dissolved after years of communication breakdown and unresolved conflict. Now engaged to David, she is determined not to repeat her past mistakes. She intentionally reflects on her first marriage, not to dwell on the pain, but to learn from it. She analyzes the conflict patterns, her role in the breakdown, and what she truly needs from a partner. This process allows her to enter her relationship with David with a profound sense of self-awareness. Wright supports this with a stark piece of data: second marriages have a statistically higher rate of divorce than first marriages. However, he offers this not as a deterrent, but as a call to action. He states that one can expect a second marriage to be tougher, but also that "you can expect this marriage to be different because you have learned many things from the failure of your first marriage." Success in a second marriage is often directly proportional to the lessons learned from the first.

Conclusion

Narrator: The single most important takeaway from 101 Questions to Ask Before You Get Engaged is that a healthy, lasting marriage is not a product of luck or blind romance, but of intentional, courageous investigation. H. Norman Wright reframes the process of asking hard questions from an act of skepticism to an act of profound love and respect—respect for oneself, for one's partner, and for the institution of marriage itself. The goal is not to find a perfect person, but to understand an imperfect person so completely that you can commit to them with your eyes wide open.

Ultimately, the book challenges a core cultural narrative. It suggests that perhaps the most romantic thing a person can do is not to fall head over heels, but to choose to walk, deliberately and with full knowledge, into a shared future. The challenge it leaves is to have the courage to seek the truth, even if it’s not what you want to hear, because a love built on reality is the only kind that has a chance to last a lifetime.

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