21 Questions to Ask Your Crush

By on January 15, 2015

Do you get butterflies in the belly every time a certain someone looks your way? Do you potentially also freeze up ever so slightly? Maybe you forget what you are about to say? Or maybe you are fully present with your guy, you just don’t really know what to ask him to have a great conversation with him and also find out as much as possible about him.

Below you will find 21 questions that work as conversation starters and that also give you an insight into your crush’s mind. You might even find out what he thinks about you whilst asking them! What’s more, you get to impress him with well thought out questions and hopefully he will ask you the same question after answering, so that he finds out about you as well.

Remember there is a certain flow to a conversations – you don’t randomly start most conversations with asking someone if they want to one day get married. Rather, let it flow and sneak in the questions whenever you can! Keep it light and keep smiling throughout.



1. What’s a Favorite Childhood Memory of Yours?

This will give you an insight into what he treasures and holds important and potentially also what shaped him to be who he is today.


2. Is There Anything That Scares You?

This can be a funny or a deep question – most of us have some irrational fears that are funny (like I still fear I will go sleepwalking as I did as a child), as well as more serious ones that we really should get rid of.


3. What’s Your Favorite City or Where Do You Think You Most Want to Live?

You can, potentially, if you live in New York for example, say something like “Is New York your favorite place to live? Do you think you’ll stay here, or would you love to move somewhere else some day?” It’s good as you figure out some of his dreams for the future, which is important if you are thinking of being in a relationship with him.

Ask him WHY he loves a certain city, favorite spots, etc. You may find similarities in what you love about a place.


Amsterdam the capital city of Netherlands


4. What Would Be Your Ideal Trip Abroad?

You can tell a lot about a person depending on how much of the world they have seen and how they would love to travel. An adventurous hike in Peru is very different from a beach vacation in Sicily.


5. What Would Be a Great Date Night / Where Would You Take a Girl if You’d Really Like to Impress Her

You will see if your sense of romance is similar and also if he ever takes you on a date, you will know how hard he is trying to impress you by comparing it to what he said.


6. What’s the Thing You Like the Most about Your Work/School?

Here you can tie it into asking about career goals and dreams for the future. Chances are you will want to date someone who is happy about their chosen profession or who is about to change into a profession they love, as they will be miserable after work every day otherwise.


7. What Do You Think the Future Will Be Like?

The Internet of Things is on its way full speed, we can soon take charter trips to the moon and life on Earth in general is changing – there’s a lot to talk about. If your crush is into tech stuff – all the better.


8. If You Could Have Three Wishes Granted, What Would They Be?

Tells you a lot about someone’s dreams and where they are at right now.



9. What’s the Most Embarrassing Thing You’ve Ever Done?

If they can’t think of anything, ask them what the cheekiest thing they’ve ever done is!


10. What Do You Think About the Concept of True Love?

Not necessarily in those words, but ask your crush if he believes in marriage, or if he prefers open relationships. A lot of people these days don’t subscribe to the idea of marrying the one person and being with them till death do them part.



11. What Are Three Things You’ve Done That You Are Really Proud of and Why?

Now you get to see if it’s helping a homeless man, or scoring high in a game of sports. A lot can be learnt from the things people are proud of.

12. What Do You Is Needed for Creating Great Relationships?

Once you know, you can give it to him!

13. What Kind of Food Do You Like?

Great to know if you are ever cooking for him, as well as if you are planning a date night.

14. What’s One Thing You Really Wanna Learn How to Do?

For some people it’s Spanish, for others it’s driving a formula one car.

15. What’s the One Thing You’d Do if You Could Change the World for the Better with a Magic Wand?

Now here’s an interesting insight into what he believes to be important for humanity and the Earth.


16. What’s Your Dream Car or Bike?

Almost all guys love talking about cars and bikes, so it’s a great way to get the conversation flowing.

17. Do You Play or Watch Any Sports?

Another one to get the conversation flowing if the guy is into his sport.

18. What’s the Craziest Thing You’ve Ever Done?

This is where you find out if he thinks it real crazy to skip one class or steal the neighbor’s car. We all have different limits in the “crazy department.”

19. Have You Read Any Book or Watched Any Movie That Truly Changed Your Life?

This question lets you find out about the things that truly move him. If he doesn’t think any books or movies were life changing, you can simply ask him

20. If You Could Be Anywhere Doing Whatever You Wanted Right Now, Where Would You Be and What Would You Do?

This gives you an insight into what his real wishes are right now.


21. What’s Your Favorite Movie Scene of All Time?

This is when you find out what makes an impression on him. The problem is if it’s James Bond throwing himself out of an airplane, you might not be able to make the same impression…



Image Source: Pinterest.com

1507760_10152392614860079_8379465670289960282_n copy 2By Maria Montgomery – Maria is a freelance writer, director and social entrepreneur. She’s also the spokesperson for The Little Angels Community Center and an avid blogger. You can find her somewhere between Cape Town, London and L.A., where you will most likely find her in the hills, looking out over the city she loves. @OhMyMontgomery



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