Christian Dating Advice: First Date Questions, Sexual Boundaries, & Pursuing Someone at Church

With DJ Logory, Be That Guy

🌟 About Coach’s Compass
Coach’s Compass is Ark’s monthly Q&A series with Christian Dating Coaches. Each edition features real questions from singles navigating the ups and downs of modern dating — and practical, faith-centered advice from coaches who get it.

Q1: What First Date Questions Reveal Someone’s True Character?

“What are some often forgotten first date questions you should ask?” — Friendly & Faithful

DJ's Answer:
When it comes to first dates, I look at them as an interview because we only really know this person based on what they’ve shared with us or any research we’ve conducted via social media or through mutual friends.
A couple of questions that come to mind are more geared towards understanding who they are when no one’s watching.
What’s really important to you?
What are three things you look for in someone?
What are you looking for in a relationship?
What’s something you struggle with?
What’s your weekly routine like?
Who are you when no one‘s watching?… The cool part about this question is that they have probably never been asked this question, so now, not only do you look like you're taking the date seriously and genuinely interested in them, but they’re probably going to remember you a little bit better as well.
This is a deep one. If the date is going well and you guys are clicking, you can try this one… When’s the last time you apologized?
This starts to test openness, honesty, and vulnerability, which are all important pieces of any relationship. I’m not saying they’re going to pour their heart out yet, see how they handle this. Could be a cool “getting to know you” experiment.

Q2: When Should Faith and Sexual Boundaries Come Up in Dating?

“How soon should you talk about waiting to have sex and living together before marriage? It feels heavy to bring up quickly, but I don’t wanna waste my time if one isn’t OK waiting on those things.” —Anonymous

DJ's Answer:
For this one, I think everybody’s opinion about timing and discussing both sex and marriage is different.
I would have this conversation when you start to really trust this person, because when it comes to sex and marriage, there is a lot of trust required in both of those areas.
Whenever you’ve gotten to the point of feeling like you can really trust this person (typically, this is after you both have expressed some vulnerabilities or broken pieces about each other, and the other listened and accepted it), and you alone truly know when you start to trust them, is when I think bringing up these conversations is appropriate.
I would try to time this conversation when things are going well, as well as when you’re thinking about the future and about you both working together as a team-- instead of individually.

Q3: How Should a Christian Man Pursue a Woman at Church?

‍“If I see a girl I like at church, what should I be praying for? How should I move forward in pursuing her while also prioritizing God and faith?” — Single in Virginia

DJ's Answer
If I see a girl that I like at church, I would first introduce myself and see if she would be open to sitting together at church.
My first prayer would be to ask God to allow me to be friendly, to be curious about learning about her, and to pray that she’s open to receiving my genuine interest.
Then, when it comes to prioritizing God, faith, and also her, I think this isn’t one or the other; this is “and”. You prioritize God and” her because she was created in the image of God, just like you were.
So I would first start with introducing myself to her, being friendly and being curious, seeing if she would be open to spending some time together, maybe grabbing some coffee, even talking about her testimony and how she came to her faith. It shows you that faith is important to you, you’re interested in her and her journey, and you’re also honoring God in that behavior as well.