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.

117c45ddb180a4e985f8a31ac60c44cd

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

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?

women

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?

kiss

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?

breakup2

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?

romantic

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?

kiss2

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?

girlinworld

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?

kiss3

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?

firstmove

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?

sleep

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?

petname

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?

workout

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?

handsome

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?

dinner2

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?

21

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?

22

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?

23

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?

24

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?

25

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?

26

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?

large

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?

27

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?

29

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?

30

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.

159 Comments

  1. Tomilayo

    August 23, 2018 at 2:32 pm

    There is this guy I think I feel for We only saw once and that was when he collected my number ever since then we have been chatting on whatsapp… I think am falling for him
    My question is Do you think I should make the move first

    • web admin

      web admin

      August 23, 2018 at 7:00 pm

      There is no reason why you can’t make the move first–it is entirely up to you. If you want to speed things up a bit, make a move. If you are fine with taking your time and getting to know him first, then there is no reason to rush things. What you do depends entirely on how fast you want this relationship to progress. Best of luck, Tomilayo!

    • Debbie

      October 8, 2018 at 9:20 am

      Yes! Go for it. He’s talking to you everyday. What have you got to lose? You have so much to gain if he says yes. Take your happiness into your own hands.

      • web admin

        web admin

        October 9, 2018 at 10:14 pm

        Thank you for sharing your positive and supportive comment. It is certain that your words will help every member of our community. Have a great day, Debbie!

  2. Flirting With Women

    August 23, 2018 at 3:01 am

    I was studying some of your articles on this internet site and I think this website is real informative ! Keep posting.

    • web admin

      web admin

      August 23, 2018 at 6:58 pm

      I am happy to hear that our articles could help you out. If you liked this topic, we have plenty more articles like it on Her Interest. Make sure to check them out! Thanks for commenting!

  3. kory

    June 17, 2018 at 11:44 am

    I like this guy and I told my friend to tell him when she did he added my snap but we don’t really have a conversation when I texted him that he could talk to me in school he said he will but he didn’t but sometimes I catch him staring at me in class what should I do

    • web admin

      web admin

      June 17, 2018 at 11:01 pm

      It is possible that he is interested in developing a relationship with you. He may not feel comfortable having conversations over snap. Speak with him in person. Share your thoughts and feelings with him. Give him a chance to share himself with you as well. Spend additional time with him in person, as this will strengthen your relationship. Have a great day, Kory!

  4. KRISTY MULLIKIN

    June 5, 2018 at 8:36 pm

    Im talking to this guy who is my best friend and we both like eachother but we arent dating yet cause im scared we will lose our friendship. How do get him to want me more and more?

    • web admin

      web admin

      June 6, 2018 at 10:07 pm

      The two of you share a strong social and emotional history. It is normal for the two of you to think about developing a relationship together. There is no reason to reason harming the other if you found the relationship based on kindness and compassion. Determine what you want for the future of this relationship. Attempt to spend additional time with him in person, as this will strengthen your relationship. Have a great day, Kristy!

  5. Bob Johnson

    April 1, 2018 at 10:45 pm

    I talk to my crush everday late at night. Mostly, I initiate the conversation but she still responds at 1 in the morning. I know she doesnt like me. Should I still try to get this to work?

    • web admin

      web admin

      April 2, 2018 at 7:48 pm

      If she has not told you that she does not like you, then she may have developed an emotional connection with you. You will find benefit in attempting to spend time with her in person. This will strengthen your relationship. Speak directly and honestly with her about your thoughts and feelings. Have a great day, Bob!

Leave a Reply

Your email address will not be published. Required fields are marked *