20 Flirty Questions to Ask Your Crush

By on September 15, 2014

When it comes to showing someone you have a crush on them, it all comes down to one thing: flirting. But if you want to kick up your flirt game and take it one step further, there’s only one way to go: flirty questions, of course! We’ve come up with an enticing list of 20 absolutely flirty and cute questions to ask your crush- all of which will make him know you like him without being overly obvious.


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


You’re asking about his perfect date, right? So it’s obvious you’re interested in him and want to know what to expect if the two of you finally decide to go out.

2. What do you look for in a girl?

perfect woman2

Obviously this is a super important question for two reasons. One, you need to know if you are even his type, and two, this lets him know that you’re curious whether or not you’re a match for him.

3. What did you think when you first saw me?


This question shows him that his opinion matters to you and you’re definitely curious what he thinks about you.

4. Where is your favorite place to be kissed?


super flirty question- make sure you remember his answer for the future ;).

5. What is your biggest turn on?

turn ons

Another incredibly flirty question that will definitely let him know you’re interested. Again, make sure you save this information for future rendezvous!

6. What is your biggest turn off?

turn off

Just like you should know what to do to turn your crush ON, you should DEFINITELY know what turns him off. Avoid these turn offs at all costs- for obvious reasons.

7. How long did your last relationship last?


Digging into his relationship history can only mean one thing: you like him and what to know if he’s in the market for something serious or if he just wants to mess around.

8. What’s the most romantic thing you’ve ever done?


As women, this is just something we should know: is he the super romantic type of guy who will sweep you off your feet? Or will he leave you hanging in the romance department?

9. How would you describe your perfect kiss?


This lets him know that you’re definitely thinking about kissing him, and you want to make sure it’s absolutely perfect for him.

10. If you could have one girl in the world, who would it be?


Really just a fun and flirty question. Extra brownie points and serious tummy butterflies if his answer is YOU.

11. What would you do if I kissed you?


This lets him know that you’re thinking about making the first move and want to know if he’d be okay with it or not. If he seems interested, I suggest going in for the kill! (Or the kiss- you catch my drift).

12. Do you like me as a friend or something more?

ask him

I don’t think this question requires any further explanation. Does he like you or not? Something you should probably find out sooner rather than later.

13. Do you like when the girl makes the first move or would you rather be in control?


Again, this is basically asking him whether or not it’s okay for you to go in and make the first move. If he’s not into that, I guess you’ll just have to sit back and wait- and keep on hinting (sigh).

14. What do you wear to bed- if anything?


Maybe you’re thinking about spending the night with him- or maybe you just want to picture him naked. Whatever the reason, this is certainly a flirty question!

15. What’s your favorite pet name you like your girl to call you?


And when he tells you the answer, go ahead and start calling him that special name every now and then- don’t forget to wink and giggle a bit, too.

16. Have you been working out?


A compliment? That’s flirting 101! Absolutely a flirty question you should ask your crush.

17. Would you rather be called sexy or smart?

sexy or smart

Is he shallow and materialist, focused on his looks, or is he more about brains and smarts? Whatever his answer, make sure to follow up with “Well you’re definitely sexy/smart”.

18. What do you think is your best feature?


After he answers, make sure to finish with something like, “Oh yeah, I totally agree. I love your ____, too”.

19. What do you think is my best feature?

Nina Dobrev

Break him out of his shell and get him to flirt back with you with this simple, flirty question.

20. Wanna go out tonight?


The ultimate flirty question. I mean, what better way to tell if your crush is crushing on you too than by asking him out on a date? It’s definitely a move for the bolder females out there, but if he says he likes it when a girl makes the first move, we highly suggest giving this question a shot.

21. Do you prefer cuddling or making out?


You can get his mind in all the right places by asking this question. What’s more flirtatious than talking about some of the most intimate things the two of you could do?

22. Do you find yourself more drawn to brains or looks?


This question maintains a certain importance and will give you insight to where his priorities lie when it comes to finding a girlfriend. Some guys must have both, others have more preference to one over the other.

23. Pick three words to describe yourself, what are they?


Letting your crush describe himself is a perfect way to get to know him and will open even more pathways to flirt with him. This question will give you a clear view of how he sees himself and if he holds any arrogant characteristics.

24. Do you know how handsome you are?


Give him a little confidence boost with this charming question. It is guaranteed to bring a smile to your crush’s cute face and really let him know what you think of him in the absolute best way possible: A compliment.

25. How would you describe your perfect relationship?


This question is a little more intense, but gets him talking about the important things and maybe give you a peek at what he expects if you two ever take your relationship to the next level. Which with these questions, should be easy!

26. Do you like dirty talk?


This one begs for a spicy answer from you beau. Get things a little heated up in your conversation by opening the doorway that will lead you two to more intimate conversations.

27. Do you like massages?


Keep things lit up with this question. It will surely give him the image of you giving him a massage after a long, hard day. Who wouldn’t love that picture? If he doesn’t love the idea of a massage from you, then he really isn’t for you, is he?

28. Are you shy or more outgoing?


It’s good to get a guy to talk a little bit about himself. He will enjoy letting you get to know him as much as he is getting to know you. Plus the answer will let you know what you are dealing with when it comes to the quickest lane out of the friend-zone and on to where you want to be.

29. What are your plans today/tonight/tomorrow/next week?


We are giving you options here, because the right one depends on your availability. But by asking him this you’re making it apparent you might want to make some sort of plans with him soon and also letting him know you care about what he has going on outside of this conversation.

30. How come no one has swooped you up yet?


Meaning how in the heck is someone like him still single. Make him blush by mixing this compliment in with this ultimately flirtatious question. Let him know you cannot believe that he is still rocking it solo. Surely this one will give him an idea of your intentions.


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