5 Questions to Ask About the Person You Are Dating

a couple in a relationship
A prayerful and practical guide for pursuing a relationship with peace, purpose, and wisdom.

There is nothing quite like the early stages of a dating relationship. The butterflies. The long conversations. The excitement of possibility. The way your phone suddenly becomes the happiest distraction in your life with every text or call from that special someone.

Dating can be beautiful, but it can also be confusing. Even when you genuinely like someone, you might find yourself wondering: Is this good? Are we building something real? Is this who God has for me?

These questions are not signs of doubt or weakness; they are signs of wisdom. Proverbs 14:15 reminds us, “The simple believe anything, but the prudent give thought to their steps” (NIV). God does not ask us to date with fear, but with discernment. Not with rigid checklists, but with open eyes and a grounded heart.

What do prudence and thought look like when applied to dating? Here are five gentle questions to help you prayerfully reflect on your romantic relationships.

1. Do I feel more like myself, or less, when I am with this person?

When God brings someone healthy into your life, you don’t need to shrink to fit. You don’t need to perform or pretend. You don’t have to work hard to be wanted.

Think about how you act around your date:

  • Do you feel comfortable being honest about who you are?
  • Do you laugh freely?
  • Do you feel pressure to always impress, always please, always be “on”?
  • Do you walk away feeling peaceful, or exhausted?

Healthy love does not drain your soul — it nourishes it. Of course, everyone gets nervous early on. But over time, the right person will help you feel more like who God created you to be, not less.

King David reminds us of this when he says, “I praise You because I am fearfully and wonderfully made…” (Psalm 139:14).If you notice yourself hiding parts of who you are, ask why. Sometimes it is insecurity that God wants to heal in you. Other times, it is a sign that something in the relationship is not aligned with who you truly are. Step back. Take a breath. Ask God, “Do I feel safe here because this is good, or only because I am afraid to be alone?”

2. Are we moving toward God together, or only toward each other?

It’s easy to get wrapped up in a person’s attention and affection. It feels good to be chosen. It feels good to have someone who wants to spend time with you, who texts you repeatedly, and who cares about the details of your day. But romantic closeness is not the same as spiritual closeness.

Ask yourself:

  • Do we talk about spiritual things naturally?
  • Do we help one another grow in character and faith?
  • Does he or she make me more intentional about pursuing Christ, or do I find myself drifting?

Picture two people walking on a path. If both are moving toward Christ, they will naturally move closer to each other. If only one is moving, eventually the distance shows.

Ecclesiastes 4:12 says, “A cord of three strands is not quickly broken.” A Christ-centered relationship is not perfect, but it is anchored. When attraction fades, when stress hits, when disagreements pop up, the foundation holds.

If you’re not sure how to begin the journey toward Christ together, start with small steps and intentionally build on them. For example, if you have not prayed together yet, pray over a meal. Pray when one of you is stressed. Pray as you part ways for the evening. These simple spiritual rhythms can reveal a lot about unity and direction.

3. What do trusted friends and mentors notice about us?

Sometimes the people who know and love you can see things you cannot see. It’s not because you are blind; it’s because feelings and infatuation can shout, while warning signs seem to whisper. Friends and mentors bring an objective set of eyes and ears, and God often uses our faith community to protect and guide us.

Ask yourself:

Have I asked for an outside perspective?

  • Do I only share the “good parts” of my relationship with my friends?
  • How does my character look in this relationship? More patient, or more reactive? More joyful, or more anxious?

You don’t need a panel of judges dictating your relationship, but you do need voices that love you and love Jesus. Proverbs 15:22 reminds us, “Plans fail for lack of counsel, but with many advisers they succeed.”

If you feel defensive when someone raises a concern, pause and pray. Ask God for clarity and humility. Sometimes the feedback stings simply because it reveals something we have been trying to avoid. The right relationship can stand wise and loving input. If someone who knows you well and walks with God consistently says, “I like who you are becoming with them,” take joy in that affirmation. It matters. But if they say, “I see something that concerns me,” that matters, too.

4. Am I honest about red flags or am I explaining them away?

No one is perfect. You are going to see flaws and quirks and the occasional emotional meltdown. That is normal and part of being human.

Red flags are different. They are habits and patterns that pull you away from who God has called you to be. They are signs of immaturity, instability, or unhealthy behaviors that may seem small now, but can have a big impact down the road.

Examples might look like:

  • Frequent jealousy or controlling behavior
  • Poor treatment of waitstaff, friends or family
  • Dismissing faith or mocking spiritual practices
  • Avoiding accountability
  • Blame-shifting or emotional manipulation

Here is a very honest question: When something concerns you, do you immediately start explaining it away? Do you say things like:

  • “They were just tired.”
  • “They didn’t mean it like that.”
  • “It’s not that big a deal.”

Grace is beautiful and necessary in dating, but grace and denial are very different. Grace does not ask you to sacrifice wisdom.

Jesus talked openly about fruit and character. “By their fruit you will recognize them,” He said in Matthew 7:16. Think about the fruit in the person you are dating, in yourself, and in your relationship. Is it good fruit? Are you growing closer to God? If you see a red flag, pause before you justify it. Invite God to show you what’s true. You don’t need to fear godly wisdom. You can use it to steward your heart in the relationship.

“Finally, brothers and sisters, whatever is true, whatever is noble, whatever is right, whatever is pure, whatever is lovely, whatever is admirable — if anything is excellent or praiseworthy — think about such things” (Philippians 4:8).

While this verse is about the things we think about, it reminds us of the good things of God that our minds should be focused on. Your relationship should ultimately lead you to focus on these things more each day.

5. Do I feel a sense of peace about this, or am I always trying to convince myself it is right?

There is a difference between occasional uncertainty and constant inner tension. Peace does not mean you never wonder, never question, never have moments of doubt. But peace has a steadiness to it. It gives rest and clarity. It gives a quiet confidence that, even if you do not know the final outcome, you are not forcing something. Anxiety feels like pushing. Peace feels like walking with God at His pace.

Ask yourself:

  • Do I feel peaceful most days about this relationship?
  • Do I sense God’s presence as I discern this?
  • Or do I always feel like I am talking myself into staying?

Philippians 4:7 promises that the peace of God guards our hearts and minds. If peace is absent, do not ignore that fact. Be still. Seek God. Bring your questions to Him without fear. God is not threatened by your uncertainty. He uses it to guide you, even in your relationships.

Inviting God into the process

You don’t have to have all the answers today. Exercising discernment isn’t a pass or fail quiz; it’s a gentle process as you learn to be intentional about your relationships. Dating with intention is less about pressure and more about posture. You don’t need to focus solely on trying to avoid mistakes. Instead, you should focus on trusting God to lead you. This is where you find peace.

Here are a few practices that can help:

  • Journal your thoughts and patterns. Notice what feels life-giving versus draining.
  • Pray one simple sentence every day. Something like, “God, lead me — and help me listen.”
  • Talk to a mentor. Let someone older and wiser speak into your dating story.
  • Do not rush peace. Wait for it. God gives it generously.

Psalm 37:23 says, “The Lord makes firm the steps of the one who delights in Him.” Your job is not to figure everything out perfectly. Your job is to walk with God, delight in Him, and trust that He will make your path clear in His time.

If this relationship is from Him, He will confirm it. If it is not, He will give you courage to let go and move toward the future He has for you. You do not need to force love. You simply need to follow God. You can trust that He will never lead you wrong. He is faithful in all things, even your relationships.

Copyright 2025 Rebecca Hastings. All rights reserved. 

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About the Author

Rebecca Hastings
Rebecca Hastings

Rebecca Hastings is a writer and speaker who loves Jesus, great stories, and making a killer chocolate chip cookie. She’s the author of three books, including Worthy: Believe Who God Says You Are, and writes to help people connect faith with everyday life. Married to her high school sweetheart, she’s a mom to three teens and young adults. Connect online at RebeccaHastings.net, and on Instagram @myinkdance.

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