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

As a seasoned relationship expert with a profound understanding of interpersonal dynamics, particularly in the realm of dating and emotional connection, I find the concept of using questions as a tool for building intimacy to be not only intriguing but also scientifically validated. The article you've presented touches upon a classic game of 20 questions, which, when employed thoughtfully, can indeed foster a deeper connection between individuals.

The reference to the 36 questions experiment by psychologists Arthur Aron, Ph.D., and Elaine Aron, Ph.D., adds a layer of credibility to the idea. Their research, published in 1997, explored whether strangers could establish a sense of closeness through a series of progressively personal questions. While it may not serve as a direct route to falling in love, their findings indicated that such interactions can promote emotional intimacy.

Now, let's delve into the specific concepts and ideas discussed in the article:

  1. The Tradition of 20 Questions: The article highlights the enduring tradition of playing 20 questions as a means of flirting and building connections. This tradition is portrayed as a timeless and effective method of engaging with a crush, not just limited to high school but applicable even in the dating landscape of one's 20s.

  2. The 36 Questions Experiment: The psychologists' experiment aimed to explore the potential for emotional intimacy between strangers through a set of increasingly personal questions. While it might not guarantee falling in love, the experiment demonstrated the efficacy of deep and meaningful conversations in establishing a connection.

  3. Flirting and Emotional Bonding: The article emphasizes the power of asking deep questions in creating a strong emotional bond between individuals. When two people open up to each other, it is portrayed as a way to form a profound and lasting connection.

  4. Sample Questions for the Game: The article provides a list of sample questions to kickstart the 20 questions game. These questions range from playful inquiries about past experiences to more reflective ones about personal preferences and values.

  5. Mix of Serious and Playful Questions: The suggested questions strike a balance between serious and playful topics, covering aspects like personal experiences, preferences, and even hypothetical scenarios. This mix is designed to make the conversation engaging and diverse.

  6. Cultural References and Humor: Cultural references, such as emojis being compared to our generation's hieroglyphs, and humorous elements, like the question about favorite dinosaurs, add a light-hearted and relatable touch to the conversation.

  7. Reflection on Life Choices: Several questions prompt individuals to reflect on their life choices, such as the preference between endless money and endless love or the desire to live in another time period. These inquiries aim to reveal deeper aspects of one's personality and values.

In conclusion, the article not only advocates for the effectiveness of the 20 questions game in building a connection with a crush but also draws on scientific research to support the idea that meaningful conversations can foster emotional intimacy. The combination of serious and playful questions, along with cultural references and humor, makes the game a dynamic and enjoyable way to deepen connections.

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