Exhausted by meaningless chit-chat when you’re out on a date? You’re not alone. Unless you’re a wordsmith — and even then, in a dating situation, you might find yourself at a loss — it can be tough to keep the conversation going.

Get Prepared.

If your date’s tongue-tied, too, it can make the experience excruciating. When it happens enough, you begin to dread the entire ghastly process.

But dating doesn’t have to be grim. In fact, it can and should be fun! Yes, you have to wade through a lot of fluff before you can find some substance.

Knowing the best date questions to ask will, however, make the exercise of separating the wheat from the chaff substantially easier.

the best questions on a date

If you can have a dialogue, you can decide if they’re right for you. If you sit there like a lump, the decision may be made for you.

Either way, an easy, natural flow to a conversation is usually kept alive by questions that require responses beyond monosyllabic replies, such as yes or no.

The best date questions are engaging and have the ability to elicit fun, interesting, and even rich discussions.

They should not, on the other hand, be a form of interrogation. Strafing your date with inquiries as if peppering them with bullets isn’t going to help your cause. 

Best Date Questions to Begin a Conversation

These first 20 examples are pretty benign and should keep you out of trouble. Starting with light topics like these can help you navigate your way through a first date while avoiding the landmines currently populating discussions both IRL and online.

The answers to these queries should give you the basics of who your date is and how they roll.

  1. What do you like to do in your free time?
  2. Are you an indoors or outdoors type?
  3. What are your favorite hobbies?
  4. Who’s the most fascinating person you’ve ever met?
  5. What’s your favorite food?
  6. What was the last book you read cover to cover that you enjoyed?
  7. Who’s your favorite author?
  8. Where have you traveled so far, and what was your favorite destination?
  9. Are you an early bird or a night owl?
  10. Which are your favorite movies?
  11. What adventures, if any, have you been on?
  12. What types of pets have you had and which are your favorite?
  13. What’s your favorite beverage (alcoholic or otherwise)?
  14. What are you currently engrossed with (societal trends, etc.)?
  15. What’s your favorite foreign or international food?
  16. What’s your favorite restaurant?
  17. If you had a choice, what would your dream job be?
  18. What would you do if you won the lottery and didn’t need to work again?
  19. What’s your favorite TV show(s)?
  20. Which programs have you binge-watched?
Best questions to ask on a date

More Best Date Questions You Can’t Go Wrong With

It’s hard to get into too much trouble with innocuous inquiries like the previous 20. But there are tons more you can bust out while remaining clear of controversy.

Here are 20 more to consider stocking your safe questions’ arsenal with.

  1. What’s your dream vacation?
  2. What trend do you think is the most over-rated?
  3. What type of music are you into?
  4. Who’s your favorite musician, singer, or band?
  5. What are some obscure things that people don’t know about you?
  6. What haven’t you tried that you’d like to try at least once in your life?
  7. Which fads do you hate to admit you followed?
  8. If you could have a superpower, which would you choose?
  9. What’s the best thing that has ever happened to you?
  10. What’s a perfect Sunday (weekend) like, in your opinion?
  11. Do you enjoy art? If so, what type(s) are you into?
  12. What’s your favorite game?
  13. Are you into sports?
  14. What do you do in your downtime?
  15. What’s your all-time favorite piece of clothing, past or present?
  16. Did you participate in sports/athletics growing up?
  17. What mobile app do you use most frequently, and why?
  18. If you could create an app, what would it do, and why?
  19. Who do you feel most comfortable around?
  20. What’s your favorite style of clothing?

Best Date Questions for Gaining More Insight

While you want to keep it light, you do want to learn something about your date beyond banal talking points.

These next 20 best date questions can further assist you in doing just that.

  1. If you could meet anyone, past or present, who would it be?
  2. If you could move anywhere, where would it be, and why?
  3. Where’s the strangest place you’ve ever been?
  4. What’s the weirdest thing you’ve ever done?
  5. What’s your silliest/most peculiar quirk?
  6. Where/when are you the most comfortable?
  7. Who or what do you most identify with?
  8. What are you personally most proud of?
  9. What would you change about your life if you could, and why?
  10. If you could, what would you change about the world, and why?
  11. What charities would you support if you could afford to?
  12. Which traits do you most value in friends?
  13. What physical characteristics about yourself do you most and least like?
  14. Is there something most people don’t know about you that might surprise them?
  15. What traits or characteristics do you pride yourself on?
  16. Is there a quality or attribute that you most deplore in other people?
  17. Are there things you have worked on regarding self-improvement?
  18. Where/when were you the happiest you’ve ever been?
  19. What is your idea of perfection?
  20. If you had one wish, what would it be?
questions to ask for the best date

Best Date Questions for Lightening Things Up

Sometimes, even with the best of intentions and the seemingly safest of subject matters, things can still take a turn and start to go awry.

If this happens to you, try and rein things in and steer the conversation back to these 20 easy-going mood lighteners.

  1. Do you possess any odd or unique talents?
  2. Do you have a nickname from childhood, or have you gained one as an adult?
  3. What’s your least and most favorite flavor of ice cream?
  4. Coke or Pepsi?
  5. Who are your most/least favorite Batman portrayers?
  6. What was your favorite cartoon as a kid?
  7. When you were a child, what or who did you want to be when you grew up?
  8. What was your most prized possession as a child?
  9. Who are your most/least favorite Joker portrayers?
  10. What’s your most prized possession as an adult?
  11. Who are your most/least favorite Bond portrayers?
  12. If you could choose any animal to be, which would you pick?
  13. X-Men or Avengers franchise?
  14. What’s the strangest situation you’ve ever found yourself in?
  15. What’s your favorite holiday?
  16. Which Christmas was your best ever, why, and how old were you?
  17. What’s the best present you’ve ever received?
  18. What’s the silliest thing you ever did as a kid?
  19. Who was your hero growing up?
  20. What’s the funniest joke you’ve ever heard?

Best Date Questions for Scratching the Surface

Being conscious of the need to shy away from controversy and avoiding digging too deep, these next 20 questions can keep the conversation rolling and help you discern more about your new companion.

  1. Which chore do you despise the most?
  2. What subject would you like to learn more about given the opportunity?
  3. Where in the world would you not want to visit, and why?
  4. What are you most guilty of doing that you recognize as needing to change?
  5. What’s your favorite guilty pleasure?
  6. Are you tech-savvy or a novice?
  7. What’s the one extravagant thing you splurge on for yourself?
  8. Where/when do you feel like a duck out of water?
  9. What’s the most excruciating social situation you could imagine?
  10. How did you and your best friend meet?
  11. What was your favorite subject in school?
  12. What was your least favorite subject in school?
  13. If you could shapeshift, what would you turn into?
  14. Which skills do you obtain that you feel you’re strongest at?
  15. What’s the worst question you’ve ever been asked?
  16. What are you most likely to procrastinate about?
  17. What’s the most outrageous thing anyone has ever said to you?
  18. What’s the most outrageous thing you’ve ever said or done?
  19. Beach or mountains?
  20. What’s your favorite season, and why?

Best Date Questions on a Slightly More Serious Note

Once the two of you have settled in and that case of nerves you’re suffering from has started to abate, there are still lots of inquiries you can make to sort out some of the questions you may yet have. Try these 20 for pealing the layers back a bit more without ruffling any feathers.

  1. What are you most grateful for?
  2. If you knew you only had a limited amount of time left, what would you do with your remaining days, weeks, months?
  3. Are you and your family close?
  4. Who/what has been the greatest influence in your life?
  5. What’s the most essential part of a non-romantic relationship?
  6. What are you most envious of?
  7. Do you consider yourself a leader or a follower?
  8. When/where are you the silliest?
  9. If you could have any question answered in full, what would it be?
  10. What’s the worst advice you’ve followed?
  11. What are the top three things you enjoy talking about?
  12. What are other people most surprised to discover about you?
  13. If you could time travel, where would you go?
  14. If you lived to be 100, which would you rather retain, your physical or mental capabilities?
  15. What are “the little things” that brighten your outlook the most?
  16. Among your friends, what’s your claim to fame?
  17. What’s the stupidest thing you’ve ever done due to boredom?
  18. If you could take anything back (said/did), what would it be?
  19. What’s the last new thing you’ve tried and how long ago was it?
  20. What’s the most spontaneous thing you can claim doing?

Best Date Questions for Looking Ahead

Get an idea of where they want to be and which direction their moral compass points with these 20 questions.

  1. Where do you see yourself in 10 years?
  2. What would you most like to be known or recognized for?
  3. At what age would you like to retire and where?
  4. What are your dreams for the future?
  5. Given a choice, would you rather live to 100 and retain your health as an unknown or check out early and famous?
  6. Which is more important to you, pride or respect?
  7. What lengths would you go to in order to secure happiness?
  8. When, in your view, is it alright to lie?
  9. Would you cheat to get what you wanted in life?
  10. Do you tend to be more inclusive or more exclusive in your outlook and behavior towards others?
  11. What is humankind’s greatest folly?
  12. Do you consider yourself flexible?
  13. What bothers you most about people?
  14. Have you ever been a volunteer in your community?
  15. What was your greatest disappointment in life?
  16. Do you believe in fate, or are we the masters of your own destiny?
  17. Have you ever helped someone less fortunate than you in a meaningful way?
  18. What do you see as the greatest challenge facing the world in the future?
  19. If you could space travel, would you?
  20. What is the greatest human achievement?
questions for a great date

Best Date Questions NOT to Ask

There are numerous questions you don’t want to pursue on a first date, and sometimes not on a second (or even third) date, either.

The first two topics that jump to mind are:

  1. Marriage. Ex: “what are your thoughts?”
  2. Kids. Ex: “do you want to have any?”

You may be dying to know, but try and refrain or suffer the consequences. These two topics can instill fear in the heart of a wary single as quickly as if you’d shown up with a bad rash plastered all over the side of your face.

You may already be aware that they’re a divorced parent, but bringing up the “more kids” question is off the table when you’re first dating.

If he or she brings theirs up, you can comment and take part in the conversation, but it might be better if the two of you actually got to know each other better first.

Besides, it’s not recommended children be introduced into early dating conversations due to safety concerns.

Take Your Time

Don’t assume that this charming man or woman is the salt of the earth just yet. It takes time to get to know someone, even if you’ve been messaging for weeks.

Being able to read someone’s body language in-person and observing how they react without a script will tell you a lot more than a chat room, forum, or any kind of messaging system you might be employing. That goes for phone calls, too. You can’t see their face, and you can’t feel tension over a phone, even if you’re able to hear it.

So, when should you bring marriage and kids up?

Well, the unwritten rule of thumb for intimate relations is generally understood to be at the end of the third date.

If you agree with that timetable and weddings or babies not happening is a deal-breaker for you, then you might want to broach the subject before the check arrives. He or she may be going home alone, but at least you know where you stand before it went any further.

what questions to ask on a date?

Other “No No” Topics

Other subjects you may want to avoid like the plague initially are everybody’s old favorites:

  1. Politics
  2. Religion

There’s a saying about them, but we’re sure you’re familiar with it. The point is, try and steer clear of any potentially controversial topics at the outset.

There’s plenty of time for arguing later.

In the meantime, find out if you enjoy being around them enough to endure the parts about them that are going to be harder to embrace. Everybody has them.

The Exception…

Having said that, if the two of you have matched due to your political or religious affiliations or points of view, well, then by all means, “coffee talk” and “discuss amongst yourselves” to your heart’s content. There’s nothing like going on a first date with a kindred spirit.

Finally, avoid getting too personal or digging too deep. If you can see your date is hesitating, looking uncomfortable, casually trying to change the subject, or being vague — thus, avoiding the questions posed to them — back off. You may be hitting a raw nerve or you’re coming off as prying and they’re emotionally pulling away. Remember we talked about interrogations?

Put the klieg light and rubber hose away. Instead, try and keep things neutral and upbeat. Read their non-verbal cues and pay heed to them. Bear in mind they’re probably just as nervous as you are, and being grilled is the last thing they desire.

Best Questions for First Dates

All of the questions provided here can be tweaked and used for a multitude of safe subjects.

These examples are merely the basis for the threads you can follow for a worry-free and non-confrontational meetup and are meant to be built on.

“When/where were you the happiest?” could be “the most content,” which are two different things. Technically, most of these questions can be spun nearly a dozen different ways, all of which would be considered genial.

Use your common sense, keep your wits about you, and try and relax and enjoy the experience, even if it doesn’t lead to a happily ever after.