“How should I ask questions on a date?”
“How do I know if I’m asking the right questions?”
These are just a few versions of the same question I get emailed nearly every week.
Your brain races with thoughts like, “What if I ask the wrong questions?” or “What if they give me answers I don’t like?”
There’s a constant fear that we’ll uncover terrible “deal-breakers,” give off the impression that we’re nosy, overanalyze every answer, or come across as boring.
Think back to your most recent date.
Were you excited?
Terrified?
Probably a little bit of both.
Dating is weird.
…and amazing when you’re actually into someone.
That’s why I wrote this post about Questions about who they are, why they do the things they do, and what they’re looking for.
Guide to Asking Questions on Dates (+ What to Listen For)
In this post, I’ll cover:
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Why asking questions on dates matters
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The questions you should be asking (and why)
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What to listen for in their answers
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PLUS: how to answer questions on dates in a way that feels authentic to you
Whether you’re nervous about your first date or have been seeing someone for months and aren’t sure where to go next, I’ve got you covered.
Let’s begin…
Related: 65 Truth or Dare Questions for Adults
Why Asking Questions on Dates Is Important
The goal of asking questions isn’t to:
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Trap someone into liking you
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“Test” them to see if they’re relationship material
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Rely on low-bar criteria like “you’ll know when you meet them”
When you ask someone questions on a date, you’re laying the foundation for:
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Connection
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Trust
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Understanding
Every healthy relationship is built on three things:
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Communication
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Compatibility
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Emotional availability
The right questions help you assess each one.
I can’t tell you how many clients have told me their relationships “just fell apart.” When I ask what happened, they’ll say things like:
“We never fought.”
“We never fought because we never talked about anything serious.”
“Whoa—you mean we should’ve talked about our values and expectations in the beginning?”
Communication is crucial. And yes, that includes talking about difficult topics early on.
Why? So you don’t find out three months in that they want ten kids and expect you to do all the work.
The right questions get to the heart of who someone is, what they value, and whether you’re compatible long-term.
Related: 180 Truth Or Dare Questions For A Date
The Golden Rule of Asking Questions on Dates
Only ask questions that you actually want answers to.
This should go without saying, but I can’t tell you how many dates I’ve witnessed where one—or both—people are asking questions just to:
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Brush up on their dating game
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Sound smart
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Turn the conversation back to themselves
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Avoid learning anything meaningful
Questions are a tool for understanding—not another way to manipulate someone into liking you.
First-Date Questions to Ask
This isn’t the time to ask heavy questions about childhood trauma or how many kids they want.
A first date is your opportunity to see how someone thinks, how well they listen, and whether you enjoy talking to them one-on-one.
The goal isn’t to find “the one.”
The goal is to find someone you’d be okay going on a second date with.
Open-Ended First-Date Questions
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What do you like to do for fun when you’re not working?
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What are you excited about these days?
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How do you usually spend your weekends?
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What made you decide to start dating again?
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If you could have a perfect day, what would it look like?
Related: 150 Truth Or Dare Questions For Teenagers
What to Listen For on a Date
Curious what I listen for when people talk about their day?
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Do they answer thoughtfully or give short, uninterested responses?
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Do they ask questions about me?
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Do they speak positively about their life, or do they sound perpetually unhappy?
Red-Flag Answers Often Include:
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Disrespect toward past partners
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No sense of direction or passion
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Constant excuses when discussing goals
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A victim mentality (“My job sucks because…”)
Healthy Answers Often Show:
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Responsibility
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Honesty
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Enthusiasm
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Empathy
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Curiosity
You don’t need to meet your soulmate to have a great conversation.
Related: 50 Questions to Improve Emotional Intimacy in Your Relationship
Questions to Determine Emotional Availability
Where many people go wrong in dating is obsessing over looks.
Is attraction important? Of course. Otherwise, you wouldn’t be here reading this.
But looks won’t keep you warm at night or create the emotional connection you’re craving.
Looks fade.
What lasts is someone’s ability to emotionally show up—for you, for themselves, and for the relationship.
Emotional Availability Questions
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What have past relationships taught you about yourself?
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What does emotional support look like to you?
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How do you usually handle arguments in relationships?
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What do you need to feel valued by a partner?
Healthy Answers
These questions require introspection, which is always a good sign.
Don’t panic if someone struggles to answer perfectly—we all have off days.
Red Flags to Watch For
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Someone who villainizes all of their exes
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Avoiding the question entirely
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Turning serious questions into jokes
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“I don’t like talking about my feelings.”
If someone tells you this, believe them.
Dating Questions to Ask When Things Get Serious
Some of the best relationship advice I ever received was this:
Ask questions after you’ve decided you like someone.
I’ve seen too many people fall hard too fast, only to be blindsided when things don’t work out.
As things get more serious, pay attention to how conversations flow.
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Do your values align?
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Do your lifestyles complement each other?
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Can you realistically build a life together?
Questions to Ask Once You Like Them
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How important is family to you?
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How important is personal growth to your happiness?
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How do you feel about work-life balance?
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What are your deal-breakers in a relationship?
Asking About the Future
Yes—you should be asking about the future once things become serious.
I can’t tell you how many emails I receive that say:
“I don’t want to seem pushy by asking about the future.”
Clarity isn’t pushy. Silence is.
Don’t wait around hoping someone brings up commitment while you’re emotionally investing.
How to Ask Without Being Creepy
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What do you see yourself building with the right partner?
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Where do you hope to be in five years?
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What does commitment mean to you?
Notice I didn’t ask, “When are we getting engaged?”
Questions You Should Be Able to Answer
If you ask these questions, be prepared to answer them too.
Ask yourself:
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Am I emotionally vulnerable?
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Can I express my needs clearly?
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Am I dating with intention—or to fill a void?
Questions are powerful. Self-awareness is even more powerful.
Dating Question Boundaries
“No” is a complete sentence.
Asking personal questions doesn’t entitle you to someone’s entire life story on date one.
If you hear something you don’t like, thank them for their honesty and change the subject.
Some conversations are better saved for later.
How to Answer Questions on Dates
“Uh huh.”
“Tell me more.”
Hearing isn’t listening.
When your date asks you a question, listen carefully—and answer authentically, not with what you think sounds right.
Connection comes from presence, not performance.
Learn how to ask better questions on dates—and how to truly listen when they ask theirs.
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