20 Deep Questions To Use In A Game Of 20 Questions With Your Crush (2024)

A game of 20 questions with your crush might seem old fashioned, but who hasn't been wooed this way at the back of a high school bus? This time-honored flirting tradition of having loads of questions to ask your crush is one of our generation's best, and that goes for dating in your 20s, too. Asking your crush 20 deep questions is a surefire way to learn more about each other while building an intimate bond.

You might have heard of the 36 questions experiment. Two psychologists, Arthur Aron, Ph.D. and Elaine Aron, Ph.D., wanted to see if a pair of strangers could feel close to each other simply by asking and answering a series of increasingly personal questions, then staring into each other's eyes. Their findings were published in 1997. While it turns out the experiment was successful at sparking emotional intimacy, the questions aren't a straightforward shortcut to falling in love.

Still, there's scientific proof that asking deep questions can help two people feel connected. When you and your crush open up to each other, you're creating a powerful emotional bond. So, playing 20 questions with your crush isn't just a fun way to pass the time —it can turn you both into human versions of the heart-eye emoji.

Here are some ideas to get you started with the 20 questions game:

1. Have You Ever Dine And Dashed At A Restaurant?

Let's hope they remembered to at least leave the server a tip.

2. Would You Rather Have Endless Money Or Endless Love?

It seems cliché, but the older you get, the more you begin to realize that love doesn't pay off your student loans.

3. Have You Ever Been In A Car Crash — And It Was Your Fault?

Who hasn't backed their mom's Subaru into a mailbox? (Not on purpose, of course!)

4. If You Could Star In A Movie, What Movie Would It Be?

I wish my life could be a combination of The Adventures of Priscilla, Queen Of The Desert, and The Emoji Movie.

5. What Is Your Most Frequently Used Emoji?

Because emojis are basically our generation's hieroglyphs.

6. What Was The Last Thing You Stole Or Shoplifted?

Everybody's got a little bit of a bad boy buried deep inside.

7. Are Platonic Relationships Or Romantic Relationships More Important To You?

Friends forever means more than just one thing.

8. Would You Want To Live In Another Time Period?

I mean, the globe might be on the verge of environmental collapse, but I feel like, in any other era, I would have been a child bride or burned as a witch.

9. What Was Your Favorite Dinosaur As A Child?

Don't tell me you didn't have one, unless you lived under a rock and never watched The Land Before Time.

10. What Are Your Sun, Moon, And Rising Signs?

If they don't know what time they were born, tell them to call up their mom. People need to know.

11. Would You Rather Someone Always Tell The Truth Or Protect Your Feelings?

Knowing this will prepare you for how much brutal honesty you should serve up down the line.

12. Who Do You Miss More: Ziggy Stardust Or Prince?

Do you ever forget that they are both gone, and then, you remember, and then you have to go through the mourning process all over again?

13. If You Had To Be Trapped On A Desert Island With One Friend, Who Would You Choose?

It's an impossible question, and there's no right answer, but try and do your best.

14. If You Could Find Out How You Were Going To Pass Away, Would You Want To Know?

Unless it’s in my sleep, I just want to be taken by surprise.

15. If You Could Only Text Or Snapchat People For The Rest Of Your Life, Which One Would You Choose?

I feel like my hands are tied just thinking about my answer.

16. Would You Prefer To Work The Night Shift Or Work Alone For Eternity?

I'd rather just work it for the rest of my life and not have a real job.

17. Would You Rather Have A Beyoncé Song Or A Taylor Swift Song Stuck In Your Head For 24 Hours?

TSwift for life.

18. If You Could Start College All Over Again, What Would You Do Differently?

I still have FOMO about not studying abroad my junior year.

19. Would You Rather Have Been In The Marching Band Or On The Debate Team In High School?

Speaking personally, I actually was in the marching band. And it ruled.

20. What's One Secret You Are Still Keeping From Your Mom?

Mom, if you're reading this right now, it was me who backed into the mailbox.

This article was originally published on

20 Deep Questions To Use In A Game Of 20 Questions With Your Crush (2024)

FAQs

20 Deep Questions To Use In A Game Of 20 Questions With Your Crush? ›

When trying to get to know someone intimately, a classic game of “20 Questions” is the perfect way to do it. The flirty questions game from your childhood can be used in today's dating world to get all the juiciest details you've ever wanted to know about your crush, and form a tight bond.

What to ask your crush in 20 questions? ›

Deep Questions to Ask Your Crush
  • What do you miss about your childhood?
  • What's your favorite thing about yourself?
  • What's your biggest regret in life?
  • What makes you the happiest?
  • What would you tell your 15-year-old self?
  • What makes you mad about society?
  • How is your relationship with your parents?
  • Are you religious?
Apr 8, 2024

What deep questions to ask your crush? ›

Deep Questions to Ask Your Crush
  • What's your favorite thing about your best friend?
  • What do you want to do in your future career?
  • Where is the most stunning place you've ever visited in person?
  • Is flirting considered cheating?
  • What is something you think people might automatically assume when you first meet you?
Oct 24, 2023

Is 20 questions a flirty game? ›

When trying to get to know someone intimately, a classic game of “20 Questions” is the perfect way to do it. The flirty questions game from your childhood can be used in today's dating world to get all the juiciest details you've ever wanted to know about your crush, and form a tight bond.

Is 21 questions a flirty game? ›

21 questions game flirty

Spice up your conversations with the ultimate flirty 21 questions game. Discover creative and exciting questions to get to know someone better and add some playful charm to your interactions.

What are 21 juicy questions? ›

Best juicy questions
  • Where is your favourite place to be kissed?
  • And where is your favourite place to kiss someone?
  • Have you ever sent a nude photograph?
  • Have you ever received a nude photograph from someone else?
  • What attracts you to someone else?
  • What do you wear to bed?
  • Have you ever had a sexy dream about someone?
Dec 15, 2023

What are some flirty 21 Questions? ›

If you're playing with your crush or on a first date, consider these flirty questions your go-to.
  • Do you believe in love at first sight?
  • What was your first kiss like?
  • What was your best kiss like?
  • What was your first impression of me?
  • What's your idea of a perfect date?
May 5, 2021

What's a good flirty question? ›

Flirty Questions To Ask a Girl
  • It keeps happening. ...
  • —Bradley, 41, Ottawa, Canada.
  • “What's the sexiest place you've ever visited?”
  • “What celebrity do you think would be best in bed?”
  • “What's one thing you want to ask me but are too nervous to?”
  • “How old were you when you first felt those, you know, feelings?”

What are 50 Questions to ask your crush? ›

50 Questions to Ask a Guy or Girl Over Text
  • What is your favorite movie of all time?
  • How do you usually spend your weekends?
  • What is the most important thing you've learned in life?
  • What's the most embarrassing thing you've ever said or done in front of someone you liked?
  • What's the last concert you went to?
Jan 13, 2023

What is 20 questions dating? ›

For those who don't know, '20 Questions' is a fun game you can play with your boyfriend! The basic idea is that your partner thinks of a place/ object/ person and you have to guess that in 20 questions or less with him answering in just 'yes' or 'no'.

How to play 20 questions over text? ›

To play the 20-question texting game, one player must pick something from their imagination; it could be an object, place, or even an obscure celebrity. Then your friend will try to guess the object you chose in 20 "Yes or No" Questions or less.

How to make 21 Questions spicy? ›

Spicy 21 Questions Exclusively for Couples
  1. What's one thing you've always wanted to try in the bedroom but haven't told me?
  2. Where is the most adventurous place you'd like to make love?
  3. What's a secret fantasy you've never shared with anyone?
  4. How do you feel about role play, and what scenario intrigues you?
Mar 4, 2024

What to ask your crush over text? ›

Getting to Know Your Crush Better
  • How do you like to spend your free time? ...
  • What's your favorite food? ...
  • What's your guilty pleasure? ...
  • Are you a morning or night person? ...
  • What are your dreams and aspirations? ...
  • What is your favorite childhood memory? ...
  • What's on your bucket list?

How to play 21 Questions with a guy? ›

The game “21 Questions” is a great game to play if you are trying to get to know someone, whether they're a friend or romantic partner. Playing the game is super easy—you just ask someone 21 questions and they have to answer each one honestly. Unlike other question games, these questions are typically more personal.

What are 20 questions to ask someone? ›

Questions to ask to get to know someone FAQs
  • What's your favorite way to spend a weekend?
  • Do you enjoy what you do for a living?
  • What's a book that you'd recommend?
  • Are you a morning person or a night owl?
  • What's your dream job?
  • Do you have any pets?
  • What's your favorite type of cuisine?
  • Do you have any siblings?
Dec 7, 2023

What's a good thing for 20 questions? ›

Make sure you choose a person, place, or thing that most people in your group know about. For example, your item could be “Marylin Monroe,” since she is famous enough that most people will be able to make guesses about her. You could also choose something like New York City, the Eiffel Tower, or even clouds or the sun.

What do you ask in 20 questions? ›

The basic premise is that one person chooses something (really anything) and gives the category it belongs to (such as person, place or thing). Then, the other player is allowed to ask up to 20 yes/no questions to try to determine what it is. Why do people love 20 Questions?

What should I ask in 20 questions? ›

  • Have You Ever Dine And Dashed At A Restaurant? ...
  • Would You Rather Have Endless Money Or Endless Love? ...
  • Have You Ever Been In A Car Crash — And It Was Your Fault? ...
  • If You Could Star In A Movie, What Movie Would It Be? ...
  • What Is Your Most Frequently Used Emoji? ...
  • What Was The Last Thing You Stole Or Shoplifted?
Oct 17, 2017

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