June 21, 2023 | Casey Fletcher

People Reveal The Best Questions To Ask On A Date To Get To Know Someone Better

Getting to know someone you've just met can be tough. You want to get to know them on a deeper level, but when it comes to asking the right questions, you're drawing a blank. You've exhausted conversation about the weather, their favourite color, and what they did on the weekend. So, now what? This exhaustive list may just help you. From ice-breakers to serious conversation starters, these people reveal their favorite questions to get to know someone better.


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#1 The Backstory Game

This isn't so much a question, but a little game you can play that can help break the ice and let you know how well you mesh together. If you're at a place like a bar or restaurant, look around the room and try to come up with backstories for other people there. It's can be a lot of fun and takes some of the pressure off while getting a feel for each other's sense of humor. It can tell you a lot about a person.


#2 Go Deep

Which parallel universe versions of yourself would you want to meet and why?

#3 Laughing Hard

At the end of Pete Holmes’ podcast You Made It Weird, he always asks, “What’s the hardest you’ve laughed?" It doesn’t have to be the literal hardest, but whatever pops in their head first. I find that question always gets a good conversation going. It usually shows who’s important to them, what’s important, etc.


#4 The Perfect Question

What level of toastiness do you like your toast?

#5 Time for Pokemon

Once, when my roommate and I were searching for a thirrd roommate for our new apartment, the first question we asked applicants was, “Who’s your favorite Pokemon?” It caught a lot of people off guard and the answer doesn’t really matter that much, but the applicants’ reaction to the question helped us filter through which ones had generally similar interests to us.


#6 Happiness

What is your idea of happiness? Seems to be pretty interesting.


#7 Take Your Pick

What's your favourite childhood memory? What's something you wish was socially acceptable? What weird habits did you have as a kid? For example, I would always hold the jug upside down when pouring milk. Do you believe there are other life forms in the universe? What fictional character do you relate to the most?

#8 A Deep Question

What do you think happens after we die? Don’t ask this on first date though, they may think you have ill intentions.

#9 Life in the Universe

"What are your thoughts on life on other planets?" Usually warrants a "Seriously?" face and I go, "No, really." And most people will answer then segue into something along those lines that they're interested in and were discussing all kinds of things. Open-ended topics are great to get to know people.


#10 Loving Yourself

What do you love most about yourself? I love asking and getting asked this question. It really makes you think about how you view yourself.


#11 Pick One

A few thought-provoking questions that I would ask someone: What are you looking forward to this week? Should everyone on the planet be striving toward a common goal? If so, what would that be? If you could teach the entire world just one concept, what would it be? What concept do you think could have the most significant positive impact on humanity?


#12 Their Least Favourite Things

"What do you hate?" Tells a lot about the person you're talking to.


#13 Good Questions

If a crystal ball could tell you the truth about yourself, your life, the future or anything else, what would you want to know? Is there something that you’ve dreamed of doing for a long time? Why haven’t you done it? What is the greatest accomplishment of your life? What do you value most in a friendship? What is your most treasured memory?


#14 This One's Hard

"What's the most difficult decision you've had to make to see your dreams come true?"

#15 Dinner With Friends

One of my favorite first date questions is, “If you could go to dinner with any three people throughout history, who would it be and why?” The answer tells you a lot about them. If they just pick three people in the 21st century they want to date that kind of lets you know where they are at.


#16 Hot Dog Questions

Is a hot dog a sandwich?

#17 Right Now

"What are you thinking right now?" I remember my dad used to ask this to me when I was a kid. I used to daydream in the car when he'd drive all around Europe, I was about six years old and really, those were the best of times. It's really nice to use when you have nothing else to say and it just gives a nice glimpse into what the other person really is thinking.


#18 Ex's Version

What is your ex's version of that breakup? People are surprisingly and unintentionally honest.


#19 All the Questions

If time was frozen for eight hours right now and you could still move around freely, what would you do? What superpower would you want and why? What makes you feel at peace? What's a hobby you've always wanted to pick up, but haven't? Is there a useless skill you have or want to learn? Anything from blacksmithing to learning dead languages.


#20 Provoke a Deep Convo

Google "36 questions to fall in love." It also works for provoking deep conversations. Or watch The Skin Deep on YouTube.

#21 Go Weird

There's a Spanish TV talking show called La Resistencia where they do a lot of silly things, and one of them is asking the guest "What's your favourite mountain?" as the TV host likes rock climbing. This shocks the guest, so he ends up talking about something about himself. Pretty funny to see the reactions.


#22 Thinking Out Loud

If you think out loud, is it really thinking? Or are you just talking to yourself?

#23 Who's Your BFF?

Once, a psychiatrist asked me in our first session, "How did you meet your best friend?" This was around 40 years ago, and my answer was that she was taking off her clothes at a party. "Oh, so you thought she'd be fun to hang around with!" To be honest, that was NOT what was going through my mind at the time, but I really liked the doctor's response and assumption, and it really helped me feel comfortable and that she would not be judgemental.


#24 What About the Universe?

If the universe is expanding, what is it expanding into?

silhouette photography of person

#25 Dinner Guests

Given the choice of anyone in the world, who would you want as a dinner guest? Would you like to be famous? Before making a telephone call, do you ever rehearse what you are going to say? What would constitute a “perfect” day for you? When did you last sing to yourself? If you were able to live to the age of 90 and retain either the mind or body of a 30-year-old for the last 60 years of your life, which would you want?


#26 Free Will

Ask someone whether or not they think free will exists. Follow up with a why or why not. This usually leads to a pretty interesting conversation.


#27 Songs and Fears

What song is playing in the back of your head? What's something that freaks you out for no good reason? What's a fact that makes people wonder why you know that? Dream vacation? If you didn't live here, where would you want to live? If you changed your name, what would it be?


#28 Starry Night

If you could spend 24 hours inside the world of any painting, which one do you choose and why?

#29 This is Weird, But it Works

Someone once walked up to me at a dinner party and asked me what my worst personality trait was. I knew her already but the idea was not to learn about me, but instead to make me think about what I'm embarrassed about myself for. Pretty weird conversation.

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#30 Waking Up

What's the first thing you think of when you wake up most days? How do you handle your anger? How long do you think you'll live?


#31 Silence in Conversation

After we're kind of past all the general small talk and I see the conversation dying down, I like asking how the other person feels about silence in conversation. Most people are a little taken aback, but it's nice to kind of set up how silence is between the two of you. Some people don't like it, and some people are very comfortable with it. Plus, it minimizes the amount of "oh boy it's sorta quiet, should I say something?" thoughts that may arise later if you know that they're comfortable with! It can also be sort of telling of their approach to life and relationships.


#32 Go Full Walking Dead

How many walkers have you killed? How many people have you killed? Why?


#33 Get Into Their Imagination

One question I like to ask people is: "If you had all the resources, time, and land available to build whatever you want (a house, a park, a monument), what would you build?" I'm no architect nor psychologist, and I know it kind of sounds like an interview question, but I believe it can trigger a very interesting discussion with that person. And you can keep asking about the reasons and details afterwards.

That question is something I came up with while I was dating my last partner. When I asked her that question, she started talking about how she would imagine her dream house, full of large windows and mosaics with a colorful garden and so on. From there, it turned into a surprisingly long and pleasant conversation.


#34 Pickles on Burgers. Yes or No?

Do you like pickles on your burger? Do you believe in Sasquatch?


#35 Your Past

Bring up either your own past or someone else’s past is guaranteed to strike a deep conversation about past versus present versus future, and how they grow from what they experience. Or, why does the alphabet need to be in a certain order?


#36 This Could Turn Weird

If you could get rid of one person with no social, legal, moral, or religious repercussions, who would it be and why?


#37 Creative

One time, I was part of a committee interviewing kids to be camp counselors and I asked one kid, "If you could pull out a string of hankies from your ear what color would they be?" That kid spent a whole 10 minutes describing each individual ear hankie.


#38 Go Historical

I like asking people what was the most historical event in their lifetime. You get a lot of interesting responses ranging from Vietnam to Princess Dianna's death or landing on the moon and the first U.S. black president. It's a wonderful conversation.


#39 Home Alone

What do you do when you're home alone? A lot of the time you discover their real personality.

#40 Their Thoughts

I sometimes ask, "What are you thinking about right now?" And I expect a genuine answer. Also, you can ask them what they think about when they are in bed right before sleep. You know, how you think about a lot of stuff before you sleep when you are vulnerable and alone.

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#41 This is Interesting

"Tell me something about you that I couldn't know just by looking at you." It's interesting what the person answers with.


#42 But Why?

"Why is your favorite book, movie, or game your favorite?" Everybody has a favorite activity, but asking them what they love about it is a great way to learn more about their interests and to learn more about them as a person.


#43 Passion

What are you most passionate about in life? What makes you angry? If you could be famous, what would you want to be famous for? If you had a million dollars to donate, what charity would you donate to and why? Give me two words to describe...


#44 30 Questions

There are like 30 questions that if asked and answered truthfully, they can make two people fall in love. One question I remember was, "Your house is burning and you can save only one object from it. What do you save?" Questions like these are really helpful to find out what the other person values in a fun way.


#45 What's New?

Ask them what’s new in their life, even if you are just meeting them. It allows them to characterize their current self as opposed to describing their “typical metrics” that everyone thinks they should use to describe themselves are, such as what they studied, where they’re from, what job they work, etc.



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