How to ask thought-provoking questions, naturally get to know someone, and enjoy dating without it feeling like an interrogation!
Question: What if the best first date of your life is the one where you stop trying to impress and start getting to know the person sitting across from you?
Unfortunately, many of us have been here: the coffee is getting cold, and the conversation has landed on the weather for the third time. Or maybe the evening swung the other way and started to feel like a job interview. Either way, you walk away without learning what you came to find out.
Here’s the good news: questions are the doorway to connection, not a threat to romance. A team of Harvard-based psychologists found that people who ask more questions, especially follow-up questions that build conversation, are better liked by the person they are talking with. In the speed-dating portion of their study, those who asked more follow-ups were more likely to get a second date (Huang et al., Journal of Personality and Social Psychology, 2017).
What does this mean? Asking questions early builds stronger connections and helps you avoid making wrong assumptions about each other. So the goal of those first few dates isn’t to impress the person. It’s to understand each other better and discover whether real connection and compatibility are there.
Keep Godly Intentions in Mind When Dating
As you search for love, keep Jesus’ words close. In Matthew 22:37-39 (NIV), He said, “‘Love the Lord your God with all your heart and with all your soul and with all your mind.’ This is the first and greatest commandment. And the second is like it: ‘Love your neighbor as yourself.’”
Did you catch the order? God comes first, and when He holds first place in your life, you can love others and yourself in a healthy way. That’s why the most important thing to discover about someone is whether they share your Christian values.
Chemistry cannot carry what shared faith is meant to hold. So pray before you date, asking God to guide your steps and your tongue. Also, get honest about your own intentions. Are you dating to enjoy meeting people, or is your end goal to be married? God’s design always starts with dating, moves into exclusive courting and engagement, and eventually leads to marriage.
One more thing, and we say it with a smile 😊… ‘You do not have to hit your date with all of these questions at once.’ That would be a bit much! But you should keep these questions tucked in the forefront of your mind. Then, as conversation flows naturally and you start getting a sense of the person across from you, pull out the card that fits the moment, lead with it, or ask when the topic comes up on its own. So, without further ado, here are the seven burning questions to carry with you while dating.
1. “When you wake up on your 65th Birthday, what do you hope your life looks like?”
We love the idea of this question because it lifts the conversation out of “what do you do for work?” and into “where are you going?” Someone who has pictured their 65th birthday has usually thought about health, faith, family, and legacy. And keep in mind, you’re not looking for an identical picture, only two pictures that could hang in the same house.
Does their future have room for a spouse, children, ministry, or travel? Also, notice what may be missing from their answer. If the vision is all about comfort and no people or purpose, that tells you something too.
2. “Who has influenced, or is currently influencing, your life the most?”
We tend to become like the people we spend time with, so the names on this list, like a grandmother, a pastor, a father, or a college roommate, reveal what your date admires most about people. It also shows where their convictions came from.
Pay attention to the tone, too. Is there gratitude, or bitterness that has never been dealt with? These things could perhaps show how they receive correction. Furthermore, since the question includes who is influencing them right now, you may also learn who has a voice in their decisions today. And that answer matters if you hope to share a future.
3. “What goal, dream, or personal improvement are you currently working on?”
Notice the words “currently working on.” Anyone can keep a someday list. But this question asks about what’s happening now, indicating whether your date is growing or merely wishing. Self-aware people can name their growth edge without getting defensive.
Also, listen for the heart behind it. Is the goal about personal character, like patience or a deeper prayer life, or only about achievement? We’ve watched many couples discover that the person who kept growing on their own is the one who keeps growing in the marriage.
4. “How would you personally define a healthy, fulfilling, and purposeful relationship?”
Every one of us carries an unspoken blueprint for love, usually drawn from the homes we grew up in or the ones we saw when we visited extended family and friends. If two people never compare blueprints, they can spend years building different houses on the same lot. So, be sure to listen for purpose.
Is their ideal relationship something that exists solely to make them happy, or do they see it as a partnership that serves God, family, and others? Their answer may also show what they learned from past relationships, whether they name lessons or only list their exes’ faults. This is also where shared faith shows up, because two people can be kind and attractive and still head in different spiritual directions.
5. “What are your intentions with me?”
You may want to ask this question after the second or third date, though! LOL! If the first date is a bust, you already know their intentions don’t match yours. I’ll also admit that this is the question that makes people squirm. However, let me encourage you: ask it anyway, and ask it kindly.
Three dates is long enough to know the connection is real and short enough that nobody’s heart has run ahead of the facts. In the end, clarity protects hearts, because without it, one person may plan a future while the other simply enjoys the company. The “intentions” question also tests integrity. A person of character answers honestly even when it’s uncomfortable. At the same time, dodging the question sends its own answer.
6. “How do you handle betrayal and being hurt? Is there anything you would consider unforgivable?”
This is a two-part question, and it lands best once warmth and trust have grown, so think of it for the dates after the first one rather than the first appetizer. Every relationship involves hurt, so how your date processes pain today previews how they may handle it with you tomorrow.
Do they hold grudges, go silent, retaliate, or work toward repair? Can they name their own part or fault in the matter? Their “unforgivable” list shows where the old wounds and real boundaries live. Setting boundaries is wise, and it’s awesome when they understand that forgiving someone isn’t the same as trusting them again.
The research is encouraging. In one study of 184 people in dating relationships and 96 married people, a person’s general tendency to forgive helped explain how satisfied they were (Kachadourian, Fincham & Davila, 2004). Another study found that forgiving partners put more effort into the relationship and handled conflict with less negativity (Braithwaite, Selby & Fincham, 2011).
7. “What’s the first thing you do or say when you’re under pressure?”
Anyone can be charming over dinner, but pressure strips away the polish. Ask this one with a smile, and you will often get a refreshingly honest answer. They may say things like, “I get quiet,” “I take charge,” “I make a joke,” or “I pray.” Their answers can show how they might treat you in a crisis, while also revealing self-awareness and emotional intelligence.
Someone who says, “My first reaction is to shut down, and I am working on it,” has handed you a gift. Follow up with, “What do you wish you did instead?” And quietly watch how your date treats the server when the order comes out wrong. Pressure can show up in small moments, too.
This one’s for our married readers… Keep courting and dating each other!
To all our married couples: ‘Dating doesn’t end at the altar.’ You need to keep dating and spending quality time together, because that’s how you:
- Maintain the covenant bond
- Reconnect
- Enjoy one another in different settings
- Keep growing stronger together.
After 32 years of marriage, we can tell you that trying new things together creates shared memories and sparks conversations you didn’t know you were missing. Try having fun conversations around these questions on your next date night:
- What’s next on your bucket list?
- What is the most amazing thing you’ve learned about yourself from our years together?
- If you could go anywhere in the world, where would that fascinating place be?
What Matters Most While You’re Dating? Ask Questions With Love, Listen With Grace
Please don’t carry these questions on your dates like a checklist! Consider them as invitations to opening fun and intriguing dialogue. A first date isn’t a trial with a verdict at the end. Instead, it’s two people discovering whether they can walk in the same direction, with God leading the journey. Keep in mind that character, including emotional maturity and integrity, is revealed over time, so let the conversation start that discovery.
Want to hear more of our heart on this topic? Watch Love Letters with Jason & Ros, E2: “The ‘D’ Word- Dating w/Purpose & Discernment!”
Putting Your Question Into Practical Application
Before your next date, choose the questions you want to keep handy and decide when each might fit into the conversation. You might save the lighter ones (the 65th birthday, influences, current goals) for the first date. Then consider asking the deeper ones (a healthy relationship, handling pressure) for the second one.
If you get to date three and beyond, pull out the weightier ones (intentions, betrayal, and forgiveness) as trust grows. Also, practice your own answers to every question, out loud or on paper, so your love interest can get to know you just as well. Finish with a prayer over your list and your date, then watch God do the rest!
If you are dating, preparing for engagement, or wondering how to build a relationship on a solid foundation, our door is open. We would be honored to talk with you!
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