I still cringe when I think about the date.
He was handsome, successful, and a deacon at his church. On paper?
A total catch. We met for coffee, and I remember trying to steer the conversation beyond the usual surface-level chatter.
But every time I’d ask something with a little more substance, he’d give a polished, perfect-sounding answer and then immediately ask what my favorite movie was.
I left that coffee shop an hour later feeling completely empty.
I knew his favorite color and what he did for a living, but I had absolutely no idea what was actually in his heart.
It was one of dozens of dates I went on before I met my husband, David, that taught me a powerful lesson: a good man is more than a good résumé.
And finding out who he really is requires asking questions that go deeper than the surface.
Christian singles are often encouraged to be “equally yoked,” and the early stages of dating are a time to discern if you share similar core values and goals.
If you’re tired of wasting your time on dates that go nowhere, I want to pour you a cup of something warm and share what I’ve learned.
It’s not about turning a date into an interrogation. It’s about being intentional.
It’s about learning to ask questions that gently peel back the layers and give you a glimpse of a man’s true character, his values, and, most importantly, his walk with God.
The Goal: From Interview to Insight
Before we get to the questions, let’s get our hearts right.
The goal isn’t to grill him with a checklist, but to spark a genuine, two-way conversation.
These aren’t pass/fail questions. They are windows.
You’re simply trying to see the view from where he stands.
A man who is serious about his faith won’t be scared off by a real conversation.
Think of it less like a job interview and more like trying to read the first chapter of a really important book.
Is it a story you want to keep reading?
Okay, ready? Let’s dive in.
The Questions That Reveal the Real Him
I’ve broken these down into three little categories: the light-hearted, the heart-deep, and the faith-focused.
They build on each other, so you can start easy and go deeper as the conversation flows.
The Light & Fun (That Secretly Go Deeper)
These are great openers that feel casual but tell you a lot about what makes him tick.
- What’s something you’re nerdy or passionate about? What lights a fire in his soul? This tells you what brings him joy and energy, whether it’s woodworking, Civil War history, or fantasy football.
- What’s a book or movie that has genuinely changed your perspective on something? This is way better than “What’s your favorite movie?” because it reveals what ideas move him and make him think.
- Who are you closest to in your life? The way he talks about his best friend or his family shows his capacity for loyalty, love, and long-term relationships.
- What does a perfect, restful Saturday look like for you? This gives you a peek into his lifestyle. Is he go-go-go, or does he value quiet and rest? It can also be a gentle way to see if church is part of his weekend rhythm.
- What’s an adventure you’d love to have someday? This speaks to his dreams and whether he has a vision for his life beyond the 9-to-5 grind.
The Heart & Character (Seeing Who He Really Is)
Once you’re both warmed up, you can wade into slightly deeper waters.
These questions reveal his character and how he navigates life.
- What’s a challenge you’ve overcome that you’re proud of? This isn’t about digging for trauma, but seeing his resilience. Does he take responsibility, or does he have a victim mentality?
- What’s one of the best pieces of advice you’ve ever received? This shows who he listens to and what wisdom he holds onto.
- How do you handle stress or a really bad day? This is huge. Does he shut down, work out, call a friend, or turn to prayer? It gives you a glimpse into his coping mechanisms.
- What do you value most in your friendships? Is it loyalty, humor, accountability? What he looks for in a friend often reflects the kind of man he is.
- What are you working toward right now? It could be a career goal, a personal project, or a spiritual discipline. This shows if he is intentional about his own growth.
The Faith & Foundation (Gently Checking the Spiritual Pulse)
Bringing up faith shouldn’t feel awkward; it should be a natural extension of getting to know someone’s core.
The key is to ask questions that invite a story, not just a “yes” or “no” answer.
- What’s your faith journey been like? This is an open-ended, non-judgmental way to ask, “How did you become a Christian?”. It allows him to share his testimony in his own words and can reveal a lot about his priorities.
- Where have you seen God show up in your life recently? This is a beautiful, positive way to gauge his daily walk with the Lord. Is he actively looking for God’s hand in his life?
- What does your church community mean to you? This question tells you about his relationship with the body of Christ. Is he involved, connected, and being fed?
- Who is someone who inspires you in your faith? This can reveal his spiritual influences and who he looks up to.
- What’s a Bible verse or story that has been important to you in this season of your life? This can give you incredible insight into what God is teaching him right now.
Finding Strength in the Waiting
Before I ever walked into that coffee shop with David, I had started praying a new kind of prayer.
Instead of praying for God to send me a husband, I started praying for the wisdom to recognize him.
I’ve tucked that prayer away in my heart, and I want to share it with you.
Lord, go before me on this date. Give me wisdom to listen more than I speak. Give me eyes to see his character and a heart to understand his journey. Quiet my anxieties and let Your peace guide our conversation. Whether this is a closed door or a new beginning, let me honor You in it. Amen.
A Final Thought: Check the Foundation
Dating as a Christian isn’t just about finding someone you have fun with; it’s about finding someone you can build a life with.
You wouldn’t build a house on a shaky foundation, and a relationship is no different.
If your foundation is Christ, you want to be with someone who shares that foundation.
These questions aren’t a magic formula, but they are a tool.
They are a way to, gently and respectfully, check the foundation.
Be brave, be curious, and be yourself.
The right man won’t be intimidated by a woman who is intentional about guarding her heart and building her life on the rock.