DATING TOOLBOX • REFLECTION QUESTIONS

💬 Questions I Keep Coming Back To

Questions for the dates, relationships, “Hmm...interesting” moments, and everything my brain likes to overthink in between. 😂

Sometimes I don't need more dating advice.

Sometimes I just need a better question.

Over the years, I've realized that some of the most helpful questions aren't things I need to ask the person sitting across from me. They're things I need to ask myself.

Questions that help me separate what I hope is happening from what is actually happening. Questions that help me notice patterns, compatibility, effort, how I feel around someone, and whether a relationship really fits the life I'm trying to build.

So I started collecting the ones I keep coming back to. ❤️

When I Really Like Someone ❤️

Because apparently liking someone is exactly when my brain becomes exceptionally talented at getting ahead of itself. 😂

• What do I actually know about this person right now?
• Am I excited about who they are, or about who I think they could be?
• What have they consistently shown me—not just told me?
• Am I seeing compatibility, or am I seeing chemistry and hoping compatibility follows?
• If I weren't attracted to this person, would I still be explaining this behavior away?
• Is there something I noticed early on that I'm now trying to convince myself doesn't matter?
• Do I like the relationship I actually have, or the relationship I imagine we could have?
• Am I learning about this person, or am I already writing the ending?
• If nothing about this person changed, would I still want this relationship?
• Am I asking, “Could I make this work?” when I should be asking, “Does this actually fit?”

When I'm Trying to Figure Out Compatibility 🧭

Chemistry matters. But eventually I also have to ask whether our lives, values, and direction actually fit.

• Does this person fit the life I'm trying to build, not just the season I'm currently in?
• Are our values actually aligned, or do we simply use similar words to describe them?
• What does faith look like in their everyday life—not just what do they say they believe?
• Do we want similar things when it comes to marriage, family, lifestyle, growth, money, travel, and where or how we live?
• Which differences between us are simply preferences, and which would affect our everyday life?
• Am I treating one of my Cannots like a preference because I like this person?
• Would being with this person require me to continually give up something I already know matters deeply to me?
• Can we disagree without one person needing the other to become more like them?
• Are we curious about each other's worlds?
• Do I feel like there's room for both of us in the life we're imagining?

When I'm Not Sure If the Relationship Is Actually Growing 🌱

This is where I come back to the RAM Model: Know → Trust → Rely → Commit → Touch.

• How is this relationship actually growing?
• Do I know this person well enough for the amount of trust I've given them?
• Has their consistency earned the amount I'm relying on them?
• Does our commitment match what we've actually built?
• Is physical or emotional closeness making the relationship feel farther along than it really is?
• Am I trying to use commitment to create security instead of allowing security to develop first?
• Are we having new experiences and conversations that help us genuinely know each other?
• What part of this relationship is growing naturally—and what part am I pulling forward?
• If I slowed this relationship down, what would I notice?
• Am I comfortable letting this relationship tell me what it is before deciding what I want it to become?

When I'm Wondering About Effort 🐝

Because sometimes “Where is this going?” is really a question about whether both people are actually helping it go anywhere.

• If I stopped initiating, what would happen?
• Am I being pursued, or am I keeping the connection alive?
• Do their actions match their interest?
• When they say they want to spend time with me, do they actually make time?
• Am I accepting crumbs because I'm excited someone is showing some interest?
• Is the effort reciprocal, even if we express interest differently?
• Do I feel wanted, or mostly confused?
• Am I paying attention to patterns or holding onto promises?
• Is this person actually available—not just single, but available with their time, energy, and intention?
• Am I trying to create momentum that isn't naturally there?

When Something Makes Me Go, “Hmm...Interesting” 🤔

Not every awkward moment is a red flag. But sometimes a little moment sticks with me for a reason.

• Why did that moment stick with me?
• Did I feel uncomfortable because something was genuinely off, or simply because it was unfamiliar?
• Is this one awkward moment—or am I starting to see a pattern?
• What did I think when it happened, before I started explaining it away?
• If my friend told me this exact story, what would I notice?
• Am I making excuses for behavior I wouldn't normally excuse?
• Did I feel respected in that moment?
• Could I bring up my concern without worrying that I'd be mocked, corrected, dismissed, or made to feel dramatic?
• What happens when I disagree with this person?
• What happens when they don't get their way?
• What happens when I don't get my way?
• How do they respond when they're uncomfortable, disappointed, embarrassed, stressed, or wrong?
• Is this a difference I can appreciate—or one I'm already learning to tolerate?

When I'm Trying to Tell Whether I Can Be Myself 🌷

A relationship shouldn't require me to slowly disappear inside it.

• Do I feel more like myself around this person—or more careful?
• Can I be silly without feeling embarrassed?
• Can I be wrong without feeling small?
• Can I learn differently from them without being treated like my way is inferior?
• Do I feel listened to, or mostly corrected?
• Can I express an opinion without preparing to defend it?
• Does this person seem genuinely interested in understanding how I think?
• Do I feel accepted, or do I feel managed?
• Am I becoming a better version of myself because I feel supported—or because I feel like I need to earn approval?
• When I'm around the people I love, does this person join my world or mostly wait for me to return to theirs?
• Do I like who I am when I'm with this person?

After a Date ☕️

My little post-date check-in before my brain turns one evening into an entire imaginary relationship timeline. 😂

• Did I have fun?
• What did I learn about them?
• What did they learn about me?
• Did I feel curious about them?
• Did they seem curious about me?
• Did conversation feel reciprocal?
• Did I feel comfortable being myself?
• Was there anything that made me think, “Hmm...interesting”?
• Do I want another date because I'm genuinely interested—or because I want them to be interested in me?
• What am I excited to learn next?
• Do I actually want to see this person again?

When Dating Is Discouraging Me 🤍

Because not every dating question needs to be about evaluating someone else. Sometimes I need to check in with my own heart too.

• Am I letting today's dating experience become a statement about my worth?
• What am I making this rejection, ghosting, or disappointing date mean about me?
• Is that actually true?
• Can something be disappointing without becoming evidence that something is wrong with me?
• What has dating taught me about myself lately?
• Where have I grown?
• What do I understand now that I didn't understand a year ago?
• What am I proud of in the way I'm dating?
• Am I measuring my dating life only by whether I've found someone yet?
• What would it look like to have a meaningful life while still wanting marriage?
• Can I want love deeply without making finding it the proof that I'm lovable?
• Where have I seen God helping me grow even when dating hasn't gone the way I hoped?

THE ONES I KEEP COMING BACK TO

❤️ My 10 Keepers

If I had to shrink this whole page down to the questions that seem to follow me through almost every season of dating, these would be them.

1. What do I actually know right now?
2. Am I seeing who they are—or who I hope they'll become?
3. Do their patterns match their words?
4. Am I asking “Could I make this work?” instead of “Does this actually fit?”
5. What part of this relationship is naturally growing—and what part am I pulling forward?
6. If I weren't attracted to them, would I still be explaining this away?
7. Do I like who I am when I'm with this person?
8. Do I actually want another date—or do I just want them to want me?
9. Is this a preference, a difference I can appreciate, or something that genuinely conflicts with what matters to me?
10. Am I letting the relationship tell me what it is before deciding what I want it to become?

One Important Thing 😂

These aren't questions for interrogating your date.

They're questions for checking in with yourself. Some belong after a first date. Some make more sense once a relationship starts getting serious. And some are for those moments when you're sitting in your car afterward thinking, “Okay...what exactly just happened?”

You don't have to answer all of them every time. Pick the question you actually need today—and start there. ❤️