Select Page

57 Best Questions To Ask Your Crush – Get to know him.

New? Start here. | This post contains affiliate links. That means that we receive a commission for purchases made on them (more info).

Need some help coming up with great questions to ask a crush? Because you’ll definitely find the best ones here.

Knowing how to talk to a guy can be difficult, let alone a guy you like! But don’t let that discourage you from striking up a conversation with your crush. All you need are some brilliant questions to ask your crush to keep the conversation moving, and to keep it interesting!

Go ahead and give these questions a try the next time you decide to strike up a conversation with your crush. And, you never know, these questions might even help you build the confidence to move things to the next level with that person.

Contents

9 Best questions to ask a crush

Sometimes asking questions can be the best way to get to know a person. It can also be the perfect way to let someone know how you feel about them without actually stating it. You’ll find that only the best questions to ask a crush are capable of doing this.

Here are the 9 best questions to ask a crush:

1. What do you do during your time off work?

This let’s you know when he’s available if you ever plan to hang out.

2. What’s your favorite dessert?

A good way of surprising him with his favorite dessert — he won’t even remember that he told you.

3. Do you think you’re a good kisser?

There’s only one way for you to find out…

4. If you had to rename yourself, what name would you choose?

Bill? …Ted? …Megatron?

5. What skill would you love to master?

Everyone has some skill they wish they could do, maybe he’s already mastered his.

6. If you saw me angry or upset, what would you do?

This question will tell you how compassionate he is, and if he cares for you, or not.

7. What’s the most spontaneous thing you’ve ever done?

Get to know his wildside that he’ll probably be proud to boast about.

8. Who knows you the best?

Whoever it is, you’ll be close to knowing a lot about him after all these questions.

9. What’s the Perfect Way to Ask Someone Out?

This allows you to know how romantic he is, unless he gives you a pretty basic answer…

9 flirty questions to ask your crush

Flirting with your crush is likely to happen, whether you realize it or not. You like this person, and you probably want them to know this to some degree. Use these flirty questions to ask your crush things that will definitely make him blush!

Here are 9 flirty questions to ask your crush:

10. What’s the most embarrassing thing you’ve ever done to get a crush’s attention?

Don’t be upset of he skips this question — no one likes to relive embarrassing moments.

11. What would make you stay up late at night?

If you’re texting him late at night, the answer is definitely you.

12. Tell me your five biggest pet peeves?

It’s always good to know what bothers your crush, so you can avoid ever bothering them.

13. What is the most romantic thing you have ever done?

This shows you his example of romantic. Hopefully, it’s something you’d find romantic.

14. Would you like to go out on a date with me?

Be bold! Be confident!

15. What was your first date like?

First dates are always awkward, so expect a good story.

16. Do you prefer cuddling or making out?

You could ask him what he prefers to do with you later down the line.

17. What’s your idea of the perfect date?

A date with you is what he should say if he’s clever.

18. Would you go out with me if I wanted you to?

Not exactly asking him out, yet giving him a chance to ask you out.

9 fun questions to ask your crush

Keep things lighthearted with these fun questions to ask your crush. These questions are both fun to ask and fun to answer, so you and your crush will both be entertained by them.

Here are 9 fun questions to ask your crush:

19. What are some nicknames you have had in your life?

There’s got to be some embarrassing ones in there!

20. What is your go-to karaoke song?

And let him promise to sing it to you one day.

21. If a genie grants you three wishes, what would they be?

Questions like this can show you how selfish a person really is. Or, how generous they are.

22. What celebrity would you trade lives with?

Someone who’s super famous? …super rich? …or, both?

23. What superpower would you have for one day?

Having a superpower for one day would mean you’d only have one day learn how to control it! Not very fun.

24. If you won the lottery, what’s the first thing you’d buy?

And, would he share it with anyone?

25. What’s the weirdest pet you would like to have?

Everyone dreams of having a wild animal as a pet, but how wild is his dream pet?

26. What do you spend way too much money on?

Hopefully, it’s something worth spending all his money on.

27. What celebrity do you have the biggest crush on?

You can easily find out his type with this question.

9 personal questions to ask your crush

An easy way to figure out what kind of person your crush is, is with personal questions to ask about what he’s done in his life. These questions aren’t going to put pressure on him, though they will make him think about how to answer them.

If he’s smart, he’ll turn the question asking around to be able to find out some personal information on you, so be prepared.

Here are 9 personal questions to ask your crush:

28. What’s the most challenging thing you have done so far?

This is something he will be proud to answer, so make sure you have a good reply.

29. What is your proudest achievement?

Another question he’ll love to answer. Who doesn’t love talking about how great they are?

30. What is the weirdest quirk your family has?

Everyone has those weird family members that ruin the family name.

31. What is the worst lie you’ve ever told your parents?

Make sure to promise you won’t tell on him if he decides to share it with you.

32. What one thing would you be most disappointed if you never got to experience it?

It’ll be interesting to know what’s on his bucket list.

33. What would your parents be surprised to learn about you?

Parents always think they know their kids more than anyone else, so anything new would come as a surprise to them.

34. What’s been the worst year of your life so far?

If he says 2020, he’s not alone with that answer.

35. What’s the best gift you’ve ever received and who was it from?

And how well does he cherish it?

36. Tell me one stupid thing you have done in your life?

It’s only one thing. You aren’t asking for every stupid thing he’s done…

7 funny questions to ask your crush

There’s no better way to lighten up a conversation than with funny questions to ask your crush. These questions will give you a sense of how humorous he is, or how serious he takes himself. Hopefully, he’s able to laugh about most of these questions.

Here are 7 funny questions to ask your crush:

37. How funny was your first-ever email address or username? Do you mind telling it to me?

He shouldn’t mind, everyone had cringy usernames back when they were preteens. And, at the time, everyone thought they were so cool.

38. What’s the most cringeworthy outfit you’ve ever worn?

Please let him have a picture to show you!

39. What’s the lamest joke you ever heard?

This joke probably goes back to his school years. School kids think everything is a joke.

40. What’s the most foolish purchase you’ve ever made?

Probably a purchase made online. You never know what’s actually coming in the mail.

41. What story do your friends still give you crap about?

Probably that time that he got all his friends in trouble because he was the only one to get got caught.

42. When was the last time you tried to do something to look cool and it ended in utter embarrassment?

Let’s hope this dates back to his time in school, or else he might be too embarrassed to bring it up.

43. Who do you have a hard time taking seriously?

Hopefully, he doesn’t uncontrollably laugh at serious situations.

7 interesting questions to ask your crush

Try these interesting questions to ask your crush about some fascinating things you wouldn’t normally talk about. These questions will spark his interests, just as well as yours. You’ll be able to learn some exciting things about his personality with these interesting questions.

Here are 7 interesting questions to ask your crush:

44. Which website do you waste most of your time on?

This answers pretty obvious. We all spend hours on YouTube watching videos we aren’t even interested in!

45. You’re invited to a dinner party what do you bring?

Does he have class and good manners? Or is he someone that would bring a can of chicken Noodle soup?

46. What’s something weird that you find attractive?

Ear lobes? Crooked teeth? Let him know you don’t judge.

47. If your house suddenly caught fire, what’s the most important object you would save?

You’ll definitely know what his prized possession is after this question.

48. What Are Your Top 3 Things to Do on the Weekend?

Some people just like to relax over the weekend, so don’t be surprised if he says nothing at all.

49. If you could be incredibly skilled at one thing, what would you choose?

After he tells you, answer him on a positive note by telling him you’ll help him achieve this skill.

50. If you had to get a tattoo right now, what would you get?

He probably has his mind already set on his first, or next, tattoo, so this won’t be too hard to answer.

7 deep questions to ask your crush

Most people don’t feel comfortable getting too deep with someone they only just like, however, these deep questions to ask your crush won’t get too personal or touchy. They’ll allow you to get to know a different side of your crush on a deeper level, that’s all.

Here are 7 deep questions to ask your crush:

51. What does your perfect day look like?

Learn how he likes to spend his days when he isn’t busy with all the things life comes up with.

52. What was one time you really stepped out of your comfort zone?

Stepping out of a comfort zone shows he’s able to make changes, even if he isn’t comfortable doing so.

53. If your life was a movie, what would it be called?

Putting a title on life isn’t something anyone would think about. He’ll find this question creative, and he’ll think the same about you.

54. When you’re angry or in a bad mood, what do you do to get yourself out of it?

A strong person is someone who’s able to control their anger, rather than physically fight.

55. What is the most beautiful thing in the world?

There’s so much beauty in this world, but only a few people actually appreciate it. Maybe he’s one of them.

56. If you could go back in time, what is one piece of advice you would give your younger self?

Not that a person’s younger self would listen! We are so stubborn when we’re young.

57. If you knew you would die in one week, what would you do?

Some people would try to have as much fun as possible, while others would try to make amends with this life. Which person is he?

Downloadable and Printable List of Questions to Ask Your Crush

Here is a downloadable and printable jpg/pdf list of questions to ask your crush (right-click the image and select Save Image As…):

More Awesome Conversation tips

Whether you’re looking for conversation tips to help you talk to your crush, boyfriend or any guy out there, we’ve got you covered with great ways to start conversations and keep them going.

  1. A simple way to keep a conversation going is to use questions to ask a guy pretty much anything. If he’s got good answers, he’s promising.
  2. Knowing how to start a conversation with a guy is a great start before actually starting a conversation with a guy.
  3. If you’re just looking for ways to keep your relationship interesting, these questions to ask your boyfriend will give you lots of things to talk about.

How to Pick the Best Questions to Ask Your Crush

You probably won’t be asking your crush every question on this list, though, if you plan to, it’s best not to ask them all in one conversation. You don’t want your crush to feel overwhelmed by all the questions coming at him at once.

So, you’ll need a good amount of questions whenever you decide to start your question asking conversation.

Here is how to pick the best questions to ask your crush:

1. Pick questions depending on the status of your relationship

It’s probably not a good idea to jump into deep or personal questions with someone you’ve just started talking to. Considering this person is only a crush, it makes sense to keep the questions fun and not to serious.

However, if you’ve been talking to this person for a while and you feel comfortable asking more personal questions, go right ahead!

2. Choose questions you, yourself, don’t mind answering

A lot of these questions are open-ended, so, your crush could easily turn them around and ask you a similar question, or the same one to get an answer out of you. You’ll most likely have to answer these questions about yourself, as well. Don’t think that your crush will give you an answer and say “next”!

3. Keep the questions interesting

You can either bore your crush with a bunch of questions or make him know that you think outside the box. Ask questions that you think he’ll want to answer. Learn what he’s interested in and ask him questions based off that. You can also ask him questions that you know will compliment him — everyone loves compliments!

In Conclusion

As we said, knowing how to talk to a guy can be hard at first, especially if you’ve got a crush on him. And, finding things to say to start a conversation with your crush isn’t the easiest either. So, use these questions to ask your crush things to keep the conversation going. Hopefully, you’ll go further than that with these questions!

About The Author

Robin Sutherns

Robin is our female dating expert, style guru and resident life coach. Her expertise has been featured on Reader's Digest, Bustle, Hello Giggles, Best Life Online, Cheat Sheet, and many more. She lives with her fiancee in Austin and loves to cook and play with her cat.

Daily Quote

Partner Videos

PARTNER VIDEOS

Don't Be The Nice Guy - 10 POWERFUL Tricks To Be The Alpha Male
Watch this video on YouTube.
More
Share
Tweet
Pin
Skip to content