Dating · Men · Relationship · Singleness · Women

Five Questions to Consider Before Dating Someone

“Should you tell a guy that you like him?”

“What were some of your concerns about that guy’s character?”

“He told me how he felt about me. Do you think we should start dating?”

My conversations about dating range from lunch-time conversations with my 8th-grade girls to coffeeshop meetups with college girls to late night couch sessions with my closest single friends. I’ve read a half-dozen books about the topic, listened to countless sermons on it, and talked it through with everyone I’m closest to.

The truth is, there are no easy answers because relationships are tricky, emotions are unpredictable, and each situation presents slightly different challenges. Many of the books I read in my teen years gave somewhat prescriptive directions on how to approach dating, and I expected my life would follow that pattern.

And yet it didn’t. At all. There has been nothing predictable about my dating life. And the books didn’t really prepare me for the “almost-relationships” that have defined my adult life, peppered with a few random dates and the guys who never said anything, but with whom I shared a brief connection.

Then again, it wasn’t the books’ fault that my life hasn’t followed a traditional script. And I know that God has a purpose for the path he’s led me down. One of the most important things I’ve learned from my own experiences is not to offer pat answers for how to approach love and dating—because everyone’s experience is vastly different.

However, in place of a “how-to manual,” I have been taught by wise mentors to ask the right questions when considering young men to be interested in. These are the questions I generally ask my friends or mentees when discussing potential guys as well. Through these questions, we’ve had good conversations about what’s important in a guy for a dating relationship and have [hopefully] avoided some unwise decisions.

There are many more questions to be asked, of course, but here’s a starting place:

  1. How is he helping me become more like Christ?

The most important question to consider about a guy or girl is how they help us become more like Christ. I recently had a conversation with a high school freshman who admitted that the boy she had been dating was distracting her from her relationship with God. And I affirmed to her that that relationship wasn’t worth it.

I, too, have been enamored by guys with whom I shared silly banter or whose attention I craved. But I knew deep down that a strong relationship would never happen with those guys because they didn’t demonstrate a love and passion for God that pushed me closer to him.

When he or she encourages you with Bible verses, prays with and for you, shares what he’s learning from the Word, and asks what God has been teaching you, then you’ll know this is a man or woman worth being with.

  1. How does he inspire me with his character, passion, dreams, and interests?

I have long desired a man who has goals and dreams for his life which will inspire me. Once I was on a date with a guy where I asked him what his passion or vision for life was. He danced around the question a bit and then asked me what mine was.

I responded immediately (since I think about this sort of thing all the time), and then he said, “Yeah! I agree. Same here.”

And I inwardly sighed because I don’t want a guy to jump on the train of my purpose—I want him to have his own purpose with whom I can meld my purpose, and together we can create something beautiful for God’s glory.

Some guys or girls are still figuring that out, which is totally fine. It took me many years to figure mine out, and I know it’s something that can change in different seasons of life. But hopefully that guy or girl has something they’re passionate about. Hopefully they have a character that stands apart—a character that serves and loves others well. Hopefully they have some dreams for their lives, and hopefully these are things that light them up, which can in turn light you up.

  1. How does he encourage me in what I love, and how do I encourage him in what he loves?

One of the most endearing qualities about a guy to me is when they show interest in what I love—specifically my teaching, writing, or involvement with theater. When they ask genuine questions about these things and encourage me in them, I feel loved and seen.

Most likely we won’t share all the same interests as our significant other but caring about them shows a character that isn’t self-absorbed. And this is a key aspect to any healthy relationship (although I admit that I have a long way to go if my future person is into sports!).

Also, when we encourage each other in the things we love, we are valuing each other as individual people, and not expecting them to be a clone of ourselves. We are allowing space for each person to be who God made them to be and encouraging them to grow in that regard.

  1. How is he growing & maturing apart from me – who is mentoring him? And how am I growing & maturing apart from him – who is mentoring me?

Mentors and others speaking wise truth into our lives are key no matter what stage of life we’re in. But especially if we’re considering a dating relationship, each person should be stabilized by godly, outside voices.

I had a conversation with a friend about a guy who had some questions in his character, and I said, “He doesn’t need to be perfect [nobody is], but he should probably have a mentor in his life who is helping him to grow and work on those things.”

If we don’t see growth in areas that concern us, we probably shouldn’t date that person—at least not right now. And if we have areas of concern in our own lives that mentors have addressed to us, we should also not be dating until we see some growth. Growth, not perfection.

We are sinners and he’s a sinner and she’s a sinner. Relationships will reveal sins in new ways, and it will require patience to work through those things together. But you need to see in the other person a character willing to work together. If there’s an immaturity in that area, the relationship probably won’t get off to a great start.

  1. Is he attractive and do I have fun with him?

I have had conversations with girls who’ve practically had a panic attack because they feel pressure to have a relationship with a guy who met all of the above requirements, yet they still weren’t attracted to him.

The pendulum swings to one of two extremes – the extreme that puts this requirement first and ignores the other four. “He’s attractive, and I have fun with him, so duh! I’m going to date him!” is the response that most junior highers or high schoolers would have.

The other extreme is the one where godly college girls have tried to follow all the rules, and they feel burdened to make the spiritual aspect be the only thing about a guy that’s important.

Yet if you do that, you may end up with an unhappy marriage, because God did create romantic and physical attraction, as well as friendship, and those should also be considered. I’ve said no to godly guys who were total gems because I didn’t feel attracted to them or feel the sparks of fun and friendship with them.

And that is okay. We need to stop making people feel guilty for not being attracted to certain guys or girls as if it were a sin. And we also need to stop pretending like the only thing to do in a godly relationship is sit around and talk about theology (even though I do think that’s pretty fun). Going to the movies is fun. Going to a theme park is fun. Going to dinner and a show is fun. And healthy relationships can have fun and glorify God through it.


I’m certainly no expert on dating. I’ve made my fair share of mistakes with guys in the past. But these questions have been helpful to me and many girls I’ve walked alongside over the years. We won’t do relationships perfectly. They always get a little messy at times. But God’s grace can redeem the messy and bring beautiful things out of saying yes to those relationships.

Because in the end, if we’re both pursuing Christ and his vision for our relationship, it will be a reflection of the Trinitarian relationship. And this is a window to the watching world of a God worthy of worship.


Photo by Priscilla Du Preez on Unsplash.





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