Make Him Think You’re Sexy By Asking Flirty Questions

Waiting around for the guy to make a move is so yesterday. Modern girls are assertive and confident enough to take matters into their own hands. Whether it’s to attract a guy you’re into or keeping the flame alive in a relationship, there are questions you can ask to hold his interest. Here are the top 20 flirty questions to ask a guy:

1. So, how come you’re so sexy/ cute/ handsome?

This is a fantastic question to ask at almost any point of the conversation. Make sure you ask the question coyly with a smile. Even when it’s unexpected and might embarrass him a little, he will feel special and happy that you think of him that way.

2. Did you work out to get that incredible body?

You hit two birds with one stone by asking this question. Not only are you complimenting him on his great physique, but you’ll also get to know him better by asking about his workout routine, which is a great conversation opener.

3. Do you find girls who make the first move intimidating?

While it’s true that many men like to be hit on, there are still guys who prefer to make the first move. This is a great question to find out what he truly likes while still offering him the potential to answer in a flirty way.

4. Which do you prefer, making out or cuddling?

This is a great question to find out if both of you are compatible. It could also be a hint for him to either cuddle or make out with you, depending on how the conversation goes from here.

5. If you can only choose one, would you prefer someone brainy or sexy?

Obviously, everyone prefers someone with both brains and looks, but by forcing him to choose only one, you’ll see where his true priority lies. There really isn’t a right or wrong answer here, and it just depends on what type of guy you want to go out with.

6. Which do you reckon is your best feature?

Although you’ll obviously have a favorite when it comes to his features, it will be interesting to see if he sees himself the way you see him. While you’re at it, you could also ask him what he thinks is your best feature to check if you’re on the same page.

7. What would you do if you’re out swimming in the public one day and lost your swimming trunks?

This is a very flirtatious question with a hint of playfulness in it. A naughty “what if” question like this can encourage him to conjure up crazy ideas and images in his mind. Now it’s up to him to take it to the next level if he wants to.

8. What do you think is the most difficult thing you’ve ever done?

Sometimes, a serious question like this is a good filter to find out whether he’s a thoughtful person or not. While he can answer this question either seriously or turn it into a playful joke, the question will serve the purpose of shedding some light on his personality.

9. Can you describe me using only three words?

Time to find out if he has been listening to you all this time! The question is a test to see if he has been paying attention to you without making it seem like you’re needy.

10. Which three words will you choose to describe yourself?

Now you can turn the question around and direct it at him. Knowing what he thinks about himself tells you a lot about his personality like whether he’s egotistical, a comedian, or somebody with low self-esteem.

11. What do you like and dislike the most when it comes to dating?

If you’re considering dating this guy, this is a very important question to ask him before progressing any further in the relationship. You’ll find out what he really wants in a relationship, and then you can decide if it’s worth it to pursue him.

12. What would you consider to be foreplay?

While this is a great question to find out if you might be sexually compatible with each other, you should only ask it if the conversation is going well. Otherwise, it might backfire and make the situation awkward.

13. What are some of the physical features you like in a girl?

If he likes what he sees in you, he will surely mention some of your features. On top of that, this is also a good question to find out how you measure up to his preferences.

14. Do you think what I’m wearing now is sexy?

This question forces him to pay attention to your looks and lets you find out if he’s really interested in you. You can ask the question while striking a sexy pose or make it funny with a goofy pose. Either way, he will look at you and that’s always a good thing.

15. Tell me, are your parents as good looking as you are?

Everyone likes to be complimented on their looks, and this question takes your conversation one level further by asking him to talk about his family, too.

16. What do you think love is?

The beauty of this flirty question is that it could lead the conversation in different directions. He could just avoid answering it by saying he doesn’t know or it could become serious, and you can have a long discussion about what each of you thinks love is.

17. Do you wear anything when you go to bed or do you sleep naked?

Find out what his sleeping habits are and saying the words “sleep naked” might make him conjure up sexy images of you sleeping naked next to him in his mind. However, only ask this question if the conversation is going well enough.

18. Do you remember when was the last time you’ve cried?

If you want to pierce through the playful surface to get to know the real person underneath, this question will make him share one of his most vulnerable moments with you, if he chooses to do so. You’ll establish a more profound bond if you’ve shared an emotional moment like that together.

19. How is it that someone like you can still manage to stay single?

Another question that kills two birds with one stone. Not only will you be complimenting him in a flirty way and letting him know you’re interested in him, but you’ll also get to know his dating history without making it seem like you’re prying.

20. What spell have you cast on me to keep making me smile?

A question like this will show him that whatever he’s been doing, he’s doing it right. Plus, it will surely bring a smile to his face too, and you know he’s someone to keep around if he really has been making you smile a lot.


    • Be confident when you ask any of these flirty questions. If you seem meek or shy, it might be confusing to him or worse, he might think you’re not actually interested in him at all!
    • Be a good listener and let him finish answering your questions before saying anything. Listen carefully to what he has to say and acknowledge that you have been paying attention to him. Never interrupt him just to talk about yourself!
    • Analyze his answers for not only are these questions great material for a conversation, but they let you separate the real deal from those looking for a short fling. However, some men can be excellent manipulators and might escape your lie detector!

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