20 Deep Questions To Ask Your Crush During A Game Of 20 Questions

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. What better way is there to get to know somebody than a game that pretty much gives you complete access to somebody's inner workings? Opening up and being vulnerable with one another is an amazing way to build an emotional bond. If you're playing 20 questions with your crush, try to receive their answers with as little judgment as possible. It'll make them all the more willing to open up to you — and opening up is totally hot.

And if they scoff at any of your questions, then you'll know your crush just isn't as emotionally available as you are. Maybe you can teach them how to be a little bit more vulnerable with the person they're dating. And if they need a little push, answer the question yourself as well! Sometimes, answering the questions you ask for yourself can lead to just as entertaining a conversation as asking them to tell you all their little quirks.

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 Accident — And It Was Your Fault?

Who hasn't backed their mom's Subaru into a mailbox accidentally?

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. Even Though The World Has Its Problems, Was Any Time Period Better Than This One?

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 Die, Would You Want To Know?

Unless I get to die in my sleep, I just want to be taken by surprise.

15. If You Could Only Email Or Text 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 Overnight 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 Rihanna Song Stuck In Your Head For 24 Hours?

Bad girl RiRi 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.