20 Good Questions to Ask Your Crush

By on September 14, 2014

Want to find out a little more about that special someone you’re crushing on? What better way to dig deeper than the surface than by the use of questions. We’ve pulled together 20 great questions to ask your crush- from basic questions to find out his interests to more prying questions that will let you know if he’s really the one for you.

6f381433364a71dc7e4a130a5c1d68c0 1. Are you seeing anyone?


This should undoubtedly be one of your first- if not the very first- question you ask your crush. Why? Because you don’t want to spend too much time getting to know someone who is already in a committed relationship.

2. What’s your favorite movie?


This is a totally laid back question you should absolutely ask for two reasons. One, you might find out the two of you have a common interest in movies. Secondly, you’ll find out a little more about his personality. Does he like comedies? He might have a relaxed, comical personality. Does he like action? He might be a bit on the dramatic side.

3. What’s your favorite genre of music?


Another easy going question that will get the same results as question number 2.

4. What’s the longest relationship you’ve ever been in?


With this question you will find out whether or not he’s interested in long term or short term relationships- and trust me, that’s something you’ll need to know for the future.

5. What’s the most embarrassing thing you’ve ever done?


Make your conversation relaxed and silly with this funny question- which is guaranteed to bring on the laughter. Don’t forget to keep the conversation rolling with a few embarrassing moments of your own!

6. Where do you see yourself in the future?


Who doesn’t love to talk about the future? It’s the topic that just keeps giving. You might find out he will be attending law school and is dead set on becoming a popular, widely known lawyer, or he might just want to see the world with the woman he loves. There’s really no question what his answer will be!

7. How would you describe the perfect woman?

perfect woman

Why wouldn’t you want to ask this? I mean, after all, if he describes a woman who is the complete opposite of you, it might mean you should stop your crush while it’s ahead. On the other hand, if his perfect lady describes you to a tee, you might have just met your soul mate.

8. What is one thing you believe in?


Just a fun question because there’s so many different answers he could come up with. Maybe he will use this opportunity to talk about his religion, or maybe he will choose to talk about reincarnation. Who knows what he believes in? But it’s definitely something you should find out ahead of time.

9. How would your friends describe you in three words?


Definitely a fun question. I wonder how his friends will describe him? Funny? Cocky? Confident? Silly? Whatever the answers may be, you will definitely learn a lot about him.

10. If you could travel anywhere in the world, where would you go?


Another fun and laid back question that I’m sure he will love answering. If he an adventurous man who wants to travel to the largest mountain in the world, or would he rather enjoy a drink on the beach?

11. What’s your fondest memory of your past?

play with hair

Dive into his past history a little bit and indulge in a nice, calm story that may warm your heart.

12. If you could date one celebrity, who would it be?


If he says someone who looks just like you, it might be a signal he likes you!

13. If you could go to dinner with one person from history, who would you choose?


Another awesome question that will tell you more about his personality. Would he choose Albert Einstein for his wisdom or Michael Jackson for his music?

14. What’s the funnest thing you’ve ever done?


Because everyone loves to relive the funnest moments of their past!

15. What is one of your worst habits?

bad habits

Not something we always WANT to answer, but it’s definitely something you should know ahead of time instead of finding out later on in the relationship.

16. Why did your last relationship end?


This one is a BIT personal, but it’s definitely something you need to find out at one point or another.

17. Who is someone you look up to?


This question is important because it will really give you a grasp on the type of man he is.

18. What is the wildest thing you’ve ever done?


You should always know just HOW wild the person you’re crushing on is. Trust me- it’s important!

19. If you could have one wish come true right now, what would you wish for?


Always an interesting question. Just make sure to tell him he can’t wish for more wishes- that’s just downright cheating!

 20. What are you doing Friday night?


Yeah, I totally just went there. Ask him out!


See? Asking your crush questions doesn’t have to be anything daunting. These are just a few examples of totally fun, cool, and laid back questions that will get you the answers you crave without being overly prying. If you’re still in need of more questions, check out “20 Flirty Questions to Ask Your Crush” blog post!


What do you think is a good question to ask your crush?


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