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.

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

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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?

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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?

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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?

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

5. What is your biggest turn on?

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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?

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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?

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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?

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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?

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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?

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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?

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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?

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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?

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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?

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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?

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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?

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

17. Would you rather be called sexy or smart?

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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?

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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?

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

20. Wanna go out tonight?

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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?

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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?

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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?

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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?

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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?

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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?

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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?

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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?

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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?

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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?

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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.





105 Comments

  1. Morgan Jones

    October 30, 2016 at 3:12 pm

    Basically i’be been speaking to this boy for 2 months ish and we’be told each other how we feel about one another as we both love each other, but we fall out so much. I don’t want to stop talking to him but yesterday night he asked me out and i said yes. It’s was going great until this evening he said to me can we just be friends until we know each other a bit better which i’m fine with but there’s a part of me that just wants to scream and shout at him to say “NO I WANNA GO BACK OUT WITH YOU” but i just can’t, anyway we’re still friends and we’re meeting up soon i think but i’m scare it’s gonna be so awkward because our conversation over snapchat is so dry and i just don’t know what to do?

    • web admin

      web admin

      October 30, 2016 at 6:47 pm

      Determine if you want to be friends only or if you want to seek a relationship with him. Any choice is perfectly acceptable. That said, it would be wise of you to further develop your friendship with him at this time. If you do not think that you want to remain friends with him, then that is also acceptable. It would be wise to be a good person in your words, actions, and thoughts toward him. Continue to remain mindful as you move into the future, Morgan!

  2. A confused person

    October 24, 2016 at 8:48 pm

    This summer a met this girl on the internet. She was amazing! I started to fall in love with her.. but than i got scared..I’m also a girl and my family is christan. My dad wouldn’t accept me.. So i told her i liked her and she said she was straight.. I was heartbroken but I realized not everyone is gonna like you. Everything was super awkward so we just stopped talking to each other. I think about her everyday and sometimes I even cry about it. I have 2 questions.. Should I reconnect with her? And judging by what I just said do you think i’m educated enough to make big decisions like my sexuality.. Thank you so much

    • web admin

      web admin

      October 26, 2016 at 2:00 pm

      There is no problem with you expressing your sexuality, in fact, it is a good thing for you to do. However, if the person that you share your feelings with turns out to be straight, then it is important for you to respect their orientation. Your family’s feelings should be respected, however, as long as you live under their roof, they may have certain requirements. Regardless of how unfair or unjust these requirements are, you may find that they will feel anger toward you for your feelings. It would be wise for you to share your feelings directly and honestly with your family if you feel confident enough to do so. Remain positive and mindful, and remember that people support and care about you.

  3. A guy who has a name but its a secret

    July 18, 2016 at 12:40 pm

    So I’m a freshman in high school and I moved about a year ago. In my old school I had a HUGE crush on my best friend but I didn’t tell her because i didn’t want to mess it up. So I was texting her recently and she sent me this:

    “I liked you in seventh grade, you know that. When you moved away at the end of the year I was devastated. I didn’t tell anyone. That whole summer there wasn’t one day that went by where I didn’t think about you. I knew you weren’t coming back but I still hoped so much that you would and it was all a joke. I don’t really know how to explain it but it hurt so bad. When we went back to eighth grade it was honestly a little easier. When it finally sunk in that you were never coming back it just made it a little easier to try and move on but I couldn’t completely do it still. By the end of the year I’d just accepted the fact that you’d forgotten about me and didn’t really care that much even though I had cared way too much. Every time I tried to move on and find someone new it didn’t really work and for a long time I didn’t know why but then I realized I still wasn’t really over you. Eventually I just gave up and turned my emotions off and stopped trying to deal with it.”

    So now I feel like a complete moron and we live an hour apart and my parents are really protective and I don’t know what to do. I thought that she would tell me that she liked me but she said she was too nervous because quite honestly girls get really nervous and bashful around me. I told her I liked her but I just don’t know if I should say something or if it would be weird because I might not see her again. Any help would be much appreciated

    • web admin

      web admin

      July 19, 2016 at 2:26 pm

      Since she has made her feelings clear with you and you only live an hour away, it is clear that the decision is up to you. If you are interested in developing a relationship with her, then speak with her directly and honestly about your feelings. It is likely that she will be willing to attempt to nourish your relationship with you if you speak with her. So do so. Remain positive and be bold. If you think that you can not handle a relationship at this time, then be clear with your feelings so she does not get mixed signals.

    • Tanya

      October 11, 2016 at 8:23 am

      Follow your heart if you love her tell her say words that should be coming out of your heart

      • web admin

        web admin

        October 11, 2016 at 10:24 am

        That sounds like great advice, Tanya–I am sure that he will appreciate getting more input. Thanks for commenting!

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