By Katie Palitto | Finding Adam Finding Eve Ministry

Let me guess: You’re about to go on a first date, and you’re already anxious about awkward silences.

What do I say? What do I ask? How do I keep the conversation flowing without it feeling like a job interview?

I’ve been there. And after fifteen years of mentoring Catholic singles through Finding Adam Finding Eve, I’ve learned this: The quality of your questions determines the quality of your date.

Surface questions get surface answers. Real questions open doors to real connection.

Here are ten questions that go beyond “So, what do you do?” These aren’t interview questions—they’re doorways to actually knowing someone.

The Ground Rules

Before we dive in, a few principles:

Don’t use all ten in one date. Pick two or three that feel natural. Let the conversation flow from there.

Listen more than you talk. The goal isn’t to showcase your questions. It’s to learn about this person.

Be ready to answer too. Any question you ask, you should be prepared to answer yourself.

Follow up. The magic isn’t in the question—it’s in going deeper. “Tell me more about that” is the most powerful phrase in dating.

The Questions

1. “What’s something you’re really passionate about right now?”

This question does something beautiful: it lets someone talk about what lights them up. Pay attention to how they answer. Do their eyes brighten? Do they lean in?

The content matters less than the energy. Someone who has passions—and can articulate them—is someone with depth.

What you’re learning: Are they curious and engaged with life? Do they have interests beyond work and Netflix? Can they articulate what matters to them?

Follow-up: “How did you get into that?” or “What do you love most about it?”

2. “What does a typical Sunday look like for you?”

This seems casual, but it reveals volumes.

For Catholics, Sunday tells you about their faith practice. Do they go to Mass? Which one? Do they have a community?

It also reveals priorities. Is Sunday for rest and relationships, or just another workday? Do they make space for what matters?

What you’re learning: Their relationship with faith, rest, community, and priorities.

Follow-up: “Which parish do you attend?” or “Do you have people you regularly go with?”

3. “What’s a challenge you’ve worked through recently?”

This question invites vulnerability without demanding oversharing. It shows how someone handles difficulty.

Listen for: Do they take responsibility or blame others? Are they self-aware? Can they talk about struggle without drowning in it? Have they grown?

A person who can articulate growth through challenge is a person capable of marriage, which is full of challenges.

What you’re learning: Emotional maturity, self-awareness, resilience, and growth mindset.

Follow-up: “What did that teach you?” or “How are you different now?”

4. “What are you most grateful for in your life right now?”

Gratitude reveals character. Research consistently shows that grateful people are happier, healthier, and better partners.

This question also shifts energy. It invites someone to reflect on what’s good—which tends to bring out the best in people.

What you’re learning: Their capacity for gratitude, what they value, and their overall outlook on life.

Follow-up: “Why is that so meaningful to you?”

5. “What’s the best advice you’ve ever received?”

This one’s sneaky good. The advice someone remembers reveals what resonates with them—their values, their struggles, their aspirations.

It also shows you who influences them. A mentor? A parent? A book? The sources we draw from shape who we become.

What you’re learning: Their values, influences, and what wisdom they’ve internalized.

Follow-up: “Who gave you that advice?” or “How has that shaped the way you live?”

6. “What kind of relationship do you have with your family?”

Family dynamics matter enormously for marriage. This question opens that door gently.

Don’t expect perfection. Every family has dysfunction. What you’re listening for is awareness. Can they speak honestly about their family without either idealizing or demonizing? Have they done the work to understand how their upbringing affects them?

What you’re learning: Family patterns, emotional health, self-awareness about wounds.

Caution: If they seem uncomfortable, don’t push. This can be tender territory. You can simply say, “We don’t have to go there if you’d rather not.”

Follow-up: “What’s something you’d want to do similarly (or differently) in your own family someday?”

7. “What’s your favorite way to spend an evening when you have no obligations?”

This reveals how someone recharges and what brings them joy when no one’s watching.

The specific answer matters less than what it shows about compatibility. If they love quiet nights reading and you love loud parties, that’s useful information.

What you’re learning: Lifestyle preferences, introversion/extroversion, capacity for rest vs. constant activity.

Follow-up: “What is it about that that you love?”

8. “What are you hoping for in the next few years?”

This is a gentle way to explore direction without asking, “Where do you see yourself in five years?” (which sounds like a job interview).

You’re listening for alignment. Are they building toward something? Is there room for relationship in that vision? Do their hopes resonate with yours?

What you’re learning: Life direction, priorities, ambition, openness to relationship.

Follow-up: “What’s drawing you in that direction?” or “What would need to happen for that to work out?”

9. “What’s something about you that surprises people?”

This invites someone to share a dimension of themselves that isn’t immediately obvious. It often surfaces interesting stories and hidden depths.

It also breaks the pattern of predictable first-date conversation. People tend to remember questions that made them think.

What you’re learning: Self-awareness, what they value that others might miss, their capacity for depth.

Follow-up: “Why do you think that surprises people?”

10. “What role does faith play in your everyday life?”

For Catholics, this is essential. Not as a test—as genuine curiosity.

You’re not looking for a theology lecture. You’re looking for authenticity. Does their faith actually shape their choices? Can they articulate it without it feeling rehearsed?

Some people go to Mass every Sunday but their faith is compartmentalized. Others are deeply integrated but don’t talk about it much. Both can be fine—but you want to understand which you’re encountering.

What you’re learning: Depth and integration of faith, spiritual practices, how faith shapes decisions.

Follow-up: “Tell me more about that” or “How has your faith journey evolved?”

The Questions to Ask Yourself

Here’s what most first-date advice misses: the questions you should be asking yourself.

Before and after every date, reflect:

Before:

  • What am I hoping to learn about this person?
  • What would make me want a second date? What would make me decline?
  • Am I showing up as my authentic self?

After:

  • Did I learn anything meaningful about who they are?
  • Did I feel respected and comfortable?
  • Do I want to know more?
  • What did my gut tell me?

These reflections matter as much as the date itself.

What NOT to Ask on a First Date

Just as important as what to ask is what to avoid:

Don’t ask: “Why are you still single?” (Rude and presumptuous)

Don’t ask: “What happened in your last relationship?” (Too much too soon)

Don’t ask: “How many kids do you want?” (Important, but not for date one)

Don’t ask: “What’s your salary?” (Obviously)

Don’t ask: Leading questions designed to test them (They’ll feel it)

First dates are for curiosity, not interrogation. Save the deeper discernment questions for later—after you’ve established mutual interest and trust.

The Art of Listening

One more thing: The best conversationalists aren’t the ones with the best questions. They’re the ones who listen best.

When they answer:

  • Make eye contact
  • Nod and respond naturally
  • Ask follow-up questions that show you heard them
  • Don’t be thinking about what you’ll say next while they’re talking

This sounds basic, but it’s surprisingly rare. Most people are so nervous on first dates that they’re half-listening while planning their next comment.

Be present. Really hear them. That alone will set you apart.

Take the Next Step

Want to go into your next date with even more clarity?

Take the Know Thyself Assessment – Understanding yourself is the foundation for understanding compatibility with others.

Read: What Is Intentional Dating? – Learn what it really means to date with purpose.

In Him,

Katie

Katie Palitto is a relationship & dating coach @Finding Adam Finding Eve ministry and co-creator of the Game of Love app.

Keywords: first date questions, questions to ask on first date, Catholic dating questions, getting to know someone, first date conversation, intentional first date

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