First Date Questions


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Everyone gets nervous on first dates.

… And this is absolutely fine! Because knowing this means being able to be better prepared for whatever comes up. So, what’s the best way to prepare for a first date? 

By making sure you have plenty of engaging, open-minded first date questions to encourage great conversations and avoid awkward silences. 

That’s why we made this specially curated list of first date questions perfect for any situation:

The Best First Date Questions

When you’re looking for topics to discuss on a first date, these questions make excellent go-to options. Each one is open-ended enough to encourage a free flow of conversation.

#1. How do you spend your free time? – Asking about work can lead to talking about frustration; ask this instead, and get right to what your date finds fun and interesting.

#2. In one word, how would you describe yourself? – Sometimes it’s good to keep it short, sweet, and to the point.

#3. Who are the special people in your life? – Getting to know more about your date’s social and family circles can help you feel closer to each other.

#4. What’s your favorite thing about your best friend? – Best friends hold a special place in a person’s life, and tell a lot about your date’s deeper personality.

#5. What were you like as a kid? – And then, how does this compare to who they are now?

#6. Is there any subject you could spend all day talking about? – This question is excellent at giving you plenty of material for future dates.

#7. What’s your favorite book? Favorite movie? – Sharing this can lead to further dates so you can experience each other’s favorite series.

#8. What’s your biggest goal in life right now? – One of the best questions to ask on a first date, because of how quickly it can help you learn what’s most important to them.

Conversation Starters

Conversation starters make it easy to know what to talk about on a first date, they give you lots of options to expand on a topic. Use these to avoid awkward silence. 

#9. What does a typical day look like for you?This is one of the most amazing blind date questions, because it’s much more inviting than “what do you do?”

#10. What sort of vacations do you like to take? – Vacations are a great topic for things to ask your date, as many people feel more themselves on vacations than when they’re at work.

#11. What’s the best present you ever gave someone? Ever received? – As far as top dating questions go, asking about their generous nature is a great way to encourage them to show off their best attributes.

#12. What’s something you want to learn or wish you were better at? – Uncommon first date questions like this are great because of the opening they make for a second date where you can learn or do that thing together.

#13. What’s Your Favorite Place on Earth? – It’s always a safe bet to ask your date to talk about the people, places, or things that make them happy.

#14. Do you consider yourself spontaneous, or more of a planner?

Then, how well does their personality match up with yours?

# Fun and Funny First Date Questions

Choosing fun and funny questions to ask someone on a first date proves that you both don’t have to be quite so nervous. Relieving any tension with fun date questions like these will go a long way towards helping your date to open up and be themselves.

#15. Is there anything you don’t eat?

Really, this question is just a setup for being able to give them a good-natured hard time about whatever it is they’re picky about.

#16. Do you have any pet peeves?

This is one of those especially good questions to ask a girl on a first date so that you can later tease her with whatever her pet peeve is.

#17. If you could wave a magic wand right now and have your life be perfect, what would that new life look like?

Lots of first date conversation ideas can come out of this one question, since it gives options for so many different answers.

#18. What’s the worst first date you’ve ever been on?

Whatever their answer is, you can lightly joke about it — and share your own worst first date stories.

#19. What’s the most embarrassing thing you can remember that’s happened to you?

Hearing about what embarrasses your date is an excellent, funny way to get to know them better.

#20. What’s a random fun fact about you?

You can ask them to come up with conversation topics for a date too, so things don’t get too one-sided!

#21. If you won a $20 million lottery, what would you do with the money?

This question will really let you learn more about what your date likes and dislikes.

#22. If you could be any person for a day, who would you choose and why?

And then, what would be the best part about their time as this other person?

#23. If you could travel back and live in any period of time, when would it be?

Are they more of a flower child, destined for the 60s? Or maybe living in Elizabethan times?

Deeper Questions

Once your first date is off to a good start, moving into deeper questions can really help to solidify the connection. 

#24. What’s the best advice anyone ever gave you?

We think this is one of the best first date conversation questions because of how it encourages your date to share what they’re grateful for in life.

#25. If you could get advice from anyone living or dead, who would you want advice from and what would you ask?

This is one of those topics for first dates that you can come back to again and again every time after that.

#26. What Makes You Unique?

Great date questions like this one encourage the person you’re with to share their favorite parts about themselves.

#27. What’s something you’re proud of having accomplished?

This is one of the best questions for a first date to help you get into what has really made that person into who they are today.

#28. When you’re old and gray and you’re looking back at your life, what do you want to be remembered for?

Save this question for when you can really tell that you’re enjoying each other’s company, or else it might come off a little too intense.

#29. What dating advice would you give the high school version of you?

Things to ask on a first date should always give you plenty more to talk about, and this question definitely does!

#30. Who has been the biggest influence on your life?

Why shouldn’t questions to ask when dating be personal enough to spark great conversations, right?

#31. What’s on your bucket list?

What someone wants to do before they die definitely makes a good first date question.

How to Ask Questions on a First Date

Now that you have a good idea of what questions to ask, it’s time to think about the best way to ask interesting questions. Really, it all comes down to 3 major things:

#1: Listen More Than You Talk

In any sort of first date situation, you should ask questions with the express intention of really listening to what your date has to say next. 

This is why the best questions for a first date all encourage your date to really open up and share what’s on their mind. Do this, and you’ll keep their interest long after your first date is over!

#2: Ask Follow-up Questions

All really good dating conversation topics can lead to a whole array of follow-up questions. 

Instead of bouncing from one question to the next without any breaks, take the time to ask related questions after listening to your date’s first answer.

#3: Be Genuine

No matter how good your questions might be, it will all be for nothing if you’re not really being yourself

While it may seem like a good idea to appear cooler than you are, this is a sure way to prevent yourself from making genuine connections on a first date.


Did you enjoy this list of great first date questions? If you take the time to memorize and practice your delivery on even just a few of them, it will make your next first date that much smoother and more enjoyable. 

Please do let us know what you think about the article in the comments below, and share if you found it helpful!

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