The title of this article might be a little deceiving. After all, five questions won’t tell you everything you need to know who someone really is! But asking the right questions can get you started in that direction. It can also cultivate a deeper conversation, getting past the small talk and building a connection that may lead to a deeper relationship as well.
I don’t know about you, but with many dates I stuck to the basics of where a guy was from, what he was majoring in, what job he had and other bland topics that told me the basics about him. I could never think up creative questions on the fly. To have a few great questions up my sleeve would have been great!
I can’t save my own dating days, but I can help yours, so here are five questions that will help guide your next date conversations to something deeper than the weather.
1. What do you like to do with your free time?
This is an easy, nonthreatening question, but it tells you a lot about a man. When he has a free evening, how does he spend it? How he responds will tell you a little about his priorities and if yours align with his. If every free moment is spent watching or playing sports, that’s important to know. If he’s heading to the mountains to hike, you might be investing in some outdoor gear moving forward! His hobbies tell you a lot about him.
2. What are some accomplishments you’re really proud of?
This is a great question because it boosts a guy’s confidence. Guys can be very insecure, especially on dates with girls they like, and letting him “brag” a little can help show a little more of his genuine self. He might struggle to answer this for fear of appearing arrogant, but once he does, you’ll learn where he spends his energies and how driven he is.
3. How did you come to know Christ?
This is essential, and it’s not at all weird to ask. This is especially important with a guy who says he’s a Christian, but you’re not sure whether he actually follows the Lord. By asking him to detail his salvation story and his walk with God, you’re holding him accountable to his spiritual claim. A guy who isn’t really following Christ won’t have a clear answer for this. It’s important to know where he’s at spiritually before moving forward into a relationship.
4. Have you changed your mind about anything as you’ve grown older/grown in faith?
This may sound like a weird question, and it’s a little deep, so save it for later in the date. It’s helpful because it makes him think. We all change our minds on issues as we mature, and if we don’t, that’s usually a sign of pride and stubbornness. How he changes his mind (if he does at all) will reveal how teachable he is.
5. What’s something you’ve always wanted to learn?
This question is fun and can open up a conversation about your respective dreams. Does he want to learn a language? Learn to juggle? Learn to do inductive Bible study? This could end up being something you do together!
Don’t be afraid to be the one asking deep questions on a date. Most people long for the small talk to end, but don’t want to be the person to go there. Go there! Embrace it confidently and don’t apologize. A kind, deep question is respected, and you’ll learn more about your date in the process.