101 Questions to Ask Before You Get Engaged

Let’s begin our journey with a gentle truth: the most loving thing you can do before engagement is to ask questions—not just any questions, but the kind that open hearts and reveal hidden corners of the soul. Imagine sitting across from someone you care about, the sunlight warm on your face, and knowing that every question you ask is a brick in the foundation of your future together. Asking questions is not about interrogation; it’s about invitation—an invitation to authenticity, vulnerability, and growth.

Many couples rush toward engagement, swept up in romance and the thrill of new love. But so often, they forget to pause and ask the questions that matter. Why? Sometimes it’s fear—fear of what they might discover, fear of rocking the boat, or fear of seeming unromantic. But the truth is, what you don’t ask now will find you later. Surprises in marriage are rarely the good kind when it comes to character, values, or dreams.

Consider the story of a couple who, after years of marriage, realized they never discussed how they handle money—or how they express anger. The result? Arguments, resentment, and a sense of betrayal. If only they had asked, ‘How do you handle stress?’ or ‘What does money mean to you?’ before the rings were exchanged.

Another couple ignored early red flags—one partner’s quick temper, the other’s reluctance to talk about the future—hoping love would conquer all. But love is not magic; it is built on understanding, acceptance, and the courage to ask hard questions. Red flags are not stop signs, but they are signals to slow down, pay attention, and talk things through.

When you ask questions, you give your partner the gift of being known. You also give yourself the gift of clarity. You learn not only about them, but about yourself—your needs, your fears, your hopes. This is the power of asking: it transforms uncertainty into understanding and turns strangers into soulmates.

So as we set out on this audiobook journey, remember: every question is a doorway. Some doors open to laughter, others to tears, but all lead you closer to the truth. And the truth is the safest place to build a life together. Let’s step through the first door, and see what lies beyond—into the heart of self-discovery and readiness for love.