5 Important Questions to Ask the Guy You’re Considering Dating

    Those first few months of talking to a guy you like can be very confusing. While you’re trying to get to know one another, the emotions are running high. It’s easy to overthink and read into situations; it’s also easy to overlook red flags. We need God’s wisdom to navigate those early stages of a relationship!

    While we can never have a potential boyfriend completely “vetted” before dating him (there is always a risk when we step toward love!), we should try to get to know the basics about a guy before jumping into a relationship with him. As someone who repeatedly made the mistake of getting to know men by dating them, I can attest that it is far better to ask questions as friends, before you’re emotionally attached.

    Following are five questions you should attempt to have him answer before you commit to a relationship with him. I’m not recommending you sit down and go through these one by one! Think of them as conversation topics to touch on as your friendship develops.


    1. What is your family like?

    A man’s relationship with his family tells a lot about him. Positive, healthy family relationships are awesome, but not every man enjoys peace or a life free of tragedy with his family. Some are children of divorce. Some have lost siblings to death or estrangement. By knowing a little more about his family, you might also discover why his personality has developed the way it has. This can explain his love languages, why he might be guarded or afraid of intimacy, and how to relate to his family should you eventually date him.


    2. What are your goals or aspirations?

    This doesn’t have to be phrased like an interrogation to discover what your guy wants to do with his life. Questions like the following all help determine his passions and gifts: “What is your major? What would you like to do with that?” “Are you considering grad school?” “What was your favorite job you’ve ever had?” This will help you see whether your own God-given passions have anything in common with his. If they do, it can make the future much easier if you do decide to date. This conversation may also give you insight into whether or not he wants a family in the future.


    3. If you could live anywhere, where you would settle?

    Some people want to stay near the place they were born and raised. Others hope to move away. Still others are open to either. I met my husband when working in another state, the one in which he was raised. We lived there for years, but eventually returned to my hometown. Because we discussed opinions about where to live when we were friends, we weren’t under the impression that we absolutely had to stay in one area for the duration of our relationship.


    4. When was your last relationship and how did it end?

    Okay, once again, this isn’t something to ask randomly. But it IS something you need to know before jumping into a dating relationship with someone. You don’t want to be someone’s rebound or backup option. As you talk casually about your families, friend groups and aspirations, relational history should eventually come out. Both you and the guy should be honest about the past, but not overly negative. For example, discuss how past relationships ended, but don’t bash your exes. It’s a necessary discussion, but shouldn’t become gossip, either.


    5. What biblical issues are most important to you?

    This is important, and it opens up a discussion of a guy’s walk with the Lord. There are many aspects to this question and it certainly can’t be answered in one conversation, so look for clues as time goes on. If you’re able to attend church together and discuss the sermon, that’s an excellent start (this is easier if you attend the same church!). If you don’t hang out in the same Christian circles, find out if you’ve read any of the same books or listen to similar podcasts. You can discuss the content and learn more about one another’s theology in the process.

    Phylicia Masonheimer
    Phylicia Masonheimer
    Phylicia Masonheimer is an author and speaker teaching women how to discern what is true, discuss the deep stuff, and accomplish God's will for their specific lives. She holds a B.S. in Religion from Liberty University, where she met her husband, Josh, and now lives in northern Michigan with her two daughters, Adeline and Geneva.


    1. I love this a lot – and I’m definitely going to use these questions with the guy I’m considering dating!

      I do have a question though: What if I feel God is calling me to love this guy, who I know has feelings for me back, but he’s dying of an incurable disease? We’re both strong in our faith and that’s been the center of our friendship for years, but it’s hard to have conversations about the future if there may not be one 4 years from now. How can I love Steve in a God-honoring way? Any suggestions would be appreciated.

        • I would say, just pray a lot about your situation. If you feel that God is calling you to love Steve, then by all means, love him. It’s very sad that he is dying of an incurable disease. However, God may be calling you to be a light and inspiration in his life as he goes through this difficult time. I would also suggest, think of the possible regret you would have to deal with in the future if you felt that you should have put more effort into your relationship, but didn’t. I know it must be a very hard situation, and I will be praying for you, but if God is calling you to something, He knows what He is doing.

          “I pray that God, the source of hope, will fill you completely with joy and peace because you trust in him. Then you will overflow with confident hope through the power of the Holy Spirit.” Romans 15:13

          If you would, please pray for me in my own situation as there is an amazing, Christ-loving guy in my youth group who I cannot seem to even say hello to because I get nervous around him. He seems to be interested in me, though, so I would appreciate prayers for trust in the Lord and peace through my anxiety and self doubt. He is so obviously devoted to the Lord and I really look up to him in any case.

    Project Inspired

    Hey there, welcome to Project Inspired. We're here to inspire you to know that God created you for a wonderful purpose. We are a community of believers who love God. You have gifts and talents from God that are unique to you, and we're here to guide you along the way.

    Read On

    4 Free Workout Apps to Help You Get Healthy From Home

    Do you want to pick up some new healthy habits but can't ever seem to find the time? You're not alone! But even if...

    How to Use Social Media for Good: 5 Tips

    Whether we want it to be or not, I would say that social media is no doubt going to continue being a part of...

    A Child’s Right to Life

    Our country is in the middle of a battle between abortion activists and the horrors of killing unborn children, and the many people and...

    Catch the Latest on TikTok and Instagram Reels!

    I’ve been having a lot of fun lately sharing videos on TikTok and Instagram Reels. There’s no doubt that social media can sometimes be...

    3 Important Lessons From Switched Every Girl Needs To Hear

    The reviews are in and Switched is a must-see movie for fall! This film is full of laughs and Freaky Friday-esque fun. But it...


    Stay connected with Project Inspired.