When it comes to breaking the ice, we don’t realize that sometimes even the most casual first date questions can reveal more than they conceal. Subsequently, we’re afraid to ask them. Sometimes, we don’t even bother to ask questions at all. But there’s the right kind of questions and the wrong kind of questions. How do you know if he or she is ready for a committed relationship? How do you know if you are? We aren’t mind readers. But with a little forethought, we can learn more about his needs by using question tools—and our own needs in the process.

Intelligent first date questions give you an edge. Much like any other endeavor in life, there’s no such thing as a guaranteed match on a first date. Or even a second date. Or a third. While first impressions don’t always lie, they don’t always reveal the whole story, either. In other words, it takes time to truly get to know someone—and chances are, two hours in a crowded restaurant is not going to unravel any compatibility (or lack thereof!) in any potential partner.

Compatibility Unmasked

So, what defines compatibility? Is it merely a question of surface physical attraction? An inexplicable animal magnetism? Common interests? Core values? Character?

The fact is, compatibility is a highly subjective and individual quality. It can’t be universally defined. And it certainly can’t be forced.

But at the heart of compatibility, there must be some shared semblance of mutual understanding of one another. Otherwise, you’re simply crossing signals without making any sort of meaningful connection.

In conclusion, a meaningful connection can only be uncovered by asking the right first date questions.

Nailing The Right First Date Questions

The key word here is the right sort of questions. No one likes to be drilled through an interrogation, particularly when it comes to dating. The more natural your line of questions are, the more relaxed and open your date will feel in answering. In short, the idea isn’t to put him or her on the spot, but let compatibility develop naturally.

Meanwhile, remember that before you ask your date the right questions, you’ll need to clarify what you’re looking for. Therefore, you may want to first ask yourself a few of these

Starting With Yourself First

  • What are some of the key characteristics I’m looking for in a relationship?
  • What sort of partner would make me feel fulfilled?
  • How committed do I want my partner to be?
  • How would I define an ideal relationship?
  • What are my own values?
  • What are my “wants”—and more importantly, what are my “needs”?

Obviously, these questions are far from casual. Nor should they be.

In other words, you’re going to want to spend some time answering them in order to clarify what your real needs and real values are.

To sum up, as the old song says, you can’t get what you want until you actually know what you want.

50 Open-Ended First Date Questions

Questions of compatibility can never be definitive. Nor can they be anything but open-ended. You can’t truly know someone until you know yourself—and subsequently, there can be no right or wrong answer.

Keep in mind that even seemingly innocuous or casual first date questions can sometimes reveal more than a deep, soul searching probe can. In short, no one wants to be put on the spot in the middle of a first date.

To clarify, avoid asking questions about past relationships, if possible. Remember, you’re both entering into this as blank slates. In the same vein, there’s always a chance he or she may have some unnecessary baggage clouding their judgements.

Certainly ice breakers are never easy. However, with a little thought and practice, you’ll probably be able to devise your own line of questions that can better accommodate your own particular needs. So, here’s a few to get started. Firstly, personality.


  • How do you spend your free time?
  • How would your friends describe you? Your co-workers? Your family?
  • What’s the strangest compliment you’ve ever received?
  • What’s your ideal Sunday afternoon?
  • Describe the most interesting person you’ve ever met. What makes them so fascinating?
  • What’s the most exciting adventure you’ve been on?
  • Can someone be too honest?
  • What’s the most spontaneous thing you’ve ever done?
  • How do you get to know and understand someone?
  • What’s one thing you feel everyone should try at least once?
  • Where do you feel most comfortable? Where do you feel out of place?
  • What’s one movie you feel is overrated?
  • In what ways are you creative? In what ways are you analytical?
  • Which is more important—intelligence or a sense of humor?


  • What would be your ideal job?
  • Where in the world would you most like to live?
  • What’s an accomplishment you’re most proud of?
  • When you were a kid, what did you want to be when you grew up? Has that changed?
  • How would you spend your time if you didn’t need to work for a living?
  • How have you changed since you were in high school?
  • What’s one thing you’re looking forward to as you grow older? One thing you’re dreading?
  • Who has been the biggest influence in your life and why?
  • What’s one task in your life you wish you didn’t have to do?
  • What’s the most exciting thing about meeting new people? The most intimidating?
  • In what ways would you change your life? In what ways would you not?
  • Is there one thing you’ve always wanted to try but never have? What’s stopped you from doing so?
  • In an ideal setting, where would you most like to see yourself ten years from now?


  • In what ways are you similar to your parents? How are you different?
  • What’s one thing you’d change about the world?
  • What do you feel says the most about a person?
  • Can individual actions make an impact on the world? If so, in what ways?
  • What’s the biggest mistake you’ve made in your life?
  • How do you express your individuality?
  • What’s one thing that best defines someone’s personality?
  • Is there such a thing as being too open-minded?
  • In what ways has the world changed over the past 10 years, both for the better and for the worse?
  • What fulfills you?
  • How would you define change: exhilarating or terrifying? What make it so?
  • What’s one thing about your life you wouldn’t trade for a million dollars?
  • In what ways are you private? In what ways are you open?
  • What inspires you the most about the world around you?

Just For Fun

  • Which one of the five senses could you never live without?
  • What’s the most absurd thing you’ve ever done?
  • If you could be a man/woman for just one day, what would you do?
  • What is the most frivolous thing in your life you couldn’t live without?
  • Have you ever used a bad pick-up line without realizing it?
  • What’s one food you wish never existed?
  • What TV show character would you most like to be?
  • Name something pointless you’ve spent money on and was glad you did.
  • If you were a band, what would your name be?

When Is Asking Too Much… Too Much?

Most importantly, keep in mind that not everyone will be comfortable being asked deeply personal first date questions right out of the gate. For instance they may have very good reasons for being guarded. On the other hand they could also be trying to hide something about their past—or even worse, their current life.

Therefore, here are some things to remember when using question tools:

  • Are they answering spontaneously? Do their answers seem forced or insincere?
  • How hesitant are they about answering your questions? How open minded are they?
  • Are they giving your questions any thought, or simply answering in brief three-word sentences?
  • Do they contradict themselves when answering your questions?
  • Are they rebutting with challenging questions of their own?
  • Are they taking your questions in good stride? Do they seem annoyed?
  • Do their answers reveal any sort of complexity? Or do they seem a little too transparent?

Is There A Question Blueprint?

In short, there’s no such thing as a definitive line of questioning. Certainly what your needs and values are will likely differ wildly from your friends or co-workers. Nor should you spring these questions up in rapid succession out of the blue. It’s a date, not a job interview. They’ll only feel relaxed and comfortable enough to answer them at the right place and the right time. Which could be your first date, in a follow up email or even six months down the road.

To sum up, choosing the right questions to ask a girl or a guy is an art form. So is a relationship. But like any great piece of art, what they reveal isn’t always apparent at first glance. Just make certain their palette suits your canvas.

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Claudia Cox

Claudia Cox is a modern communication expert who gives singles and couples alike the tools they need to improve their relationships. She is the creator of The Text Weapon Texting Club, and the author of French Seduction Made Easy. She loves the outdoors, baking tasty treats for friends, and of course, texting.
Learn more about French Seduction Made Easy.

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