Flirty Questions to Ask a Guy You Like

One of the most misunderstood lessons in dating is that the guy MUST start flirting and aggressively pursue the woman he likes. Maybe this was a belief fifty years ago, but it’s much harder to accept nowadays – especially considering that many women complain they don’t like it when men approach them and start asking them out directly.

The truth is, there has to be more communication between both sexes before dating can proceed. There has to be an introduction. There has to be a friendly conversation and a positive vibe. From there, a man can work his way into asking her out, so he can keep the conversation going though texts or phone and create an attraction that way.

But in most cases, or shall I say, in most cases where the guy actually GETS a date, the woman helps to start the fun and sexy conversation. If she doesn’t, the man immediately senses that she’s not interested and gives up – as he should.

Yes, dating is not just all about the guy’s confidence. You have to help him out by making him feel comfortable and encouraging him to keep trying. In many cases, guys will not directly ask you out, either because of shyness or because they’re not sure if you’re being flirty or friendly.

What you might try then is using flirty questions to show the hesitant guy that YES you are into him and yes, he needs to keep chasing you. Here are twelve questions that work very well in sending a clear message: YES, I LIKE YOU.

1. “Have you been working out OR Have you been losing weight?”

An easy opener, since it gives him a compliment. Make him feel good about himself and let him know that you’re noticing his body. Great line!

2. “So does your girlfriend _____?”

Whatever you say in the second half of the sentence is irrelevant. Something like “Does you girlfriend choose your ties?” works because you are always so well dressed!” works because you’re just asking him in a cute way if he’s single. You’re also letting him know that you SHOULD have a girlfriend and it would be hard to believe you don’t. Nice flirty introduction.

3. “How did you get to be so handsome?”

This line is a little more obvious but guys really do like it! Whether you use “handsome”, or cute, or adorable is up to you. But guys are usually never complimented, because they’re so used to chasing after women and using words like “beautiful”, “pretty” and so on. Reversing the process lets a man know you like him, at least in a platonic sense. So you may have to also use the next question…

4. “Why have you been on my mind lately? Did you put a hex on me?”

This is a funny line, of course, but letting a man know you’re thinking about him is just about the most obvious sign you can give, without coming on too strong. As soon as you ask this question, or use a variant statement like “I’ve been thinking about you lately…” he knows you’re reaching out to him.

5. “What do you find sexy in a woman?”

This is a hypothetical “friendly” question but it works brilliantly. You get him thinking about sex and attraction…and then you get to act the part by doing something (or wearing something) that he likes. He gets the message very quickly.

6. “Hey can I get your opinion on this?”

Men are visual creatures so of course sending them a picture is a great honor. Naturally, you’re a little shy about sending anything too risqué at first, since you don’t want to give a “one night stand” kind of message. Here’s an idea: ask him for his opinion on a dress or a new haircut. He will definitely feel the attraction, but you’ll still be encouraging him to start flirting first.

7. “How do you sleep at night?”

Don’t say this after the guy confesses something kinky! No, instead, work it into one of those long phone conversations. You can say something innocent like “Why is it so hot at night? I need air conditioning…” to get it started. But you can eventually ask him what he wears to sleep, whether it’s pajamas or nothing. And in most cases, even a shy guy will be happy to tell you.

8. “What was your first impression about me?”

This is an interesting question because it gives him an opening to be honest about his feelings (without begging for it) AND it lets you gauge where he’s at in his attraction. Is he curious or has been hiding feelings for a long time?

9. “How is it that no matter what kind of mood I’m in, you can always make me smile?”

This is actually one of the best questions you can ask because it lets your crush know that he makes you happy. As we often discuss here, men are motivated to give, to provide to women. So telling a man that he can make you smile, even if you’re having a bad day, will encourage him to keep chasing you.

10. “Do you consider yourself shy? Or do you usually make the first move with a girl?”

This is what we call a “double bind” and it’s a fun way to ask a question.

11. “What kind of pet names do you use for your girlfriend?”

A wonderful question because it gives him the feeling of what it would be like to be sweet and flirty with you and choose a name that he likes. But if he’s never thought about it before, go with this next one…

12. “How do you impress a woman you really like?”

Finally, frame it in such a way that he explains what he WOULD do, if he was trying to impress a woman. By explaining to you what he does to impress a woman he likes, he’s actually thinking about you. This gives him an opportunity to gauge your interest in him. And that’s when you give him another signal to keep it coming.

In closing, yes, guys do make the first move but a woman really makes the first connection. You’re the one who gives him the go ahead and gives him inspiration to try harder to impress you. So if there’s a problem getting the relationship started, ask away!

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Talk soon,

Matthew Coast

P.S. If you’ve been banging your head against the wall because you’ve fallen for a man who’s frustratingly unavailable…

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About The Author

Matthew Coast

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1 Comment

  • Riza

    Reply Reply April 7, 2019

    Hi.Matthew all the topics are very interesting. Thankyou very much.

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