Flirty Questions to Ask a Guy & Leave Him Thinking of You

Flirty Questions to Ask a Guy & Leave Him Thinking of You

Want the best flirty questions to ask a guy ever? Want him to think of you or get him interested in you over text or in person? This is all you need!

Want to start something, but aren’t sure how to go about it? These flirty questions to ask a guy are the perfect start to leave him thinking of you.

So, you like this guy, but you aren’t sure if he likes you back. What do you do? You can wait for him to come to you, but that could take forever depending on the guy. Or you can just use the right kind of flirty questions over text or in person and leave him thinking of you, all the time.

Flirty questions to ask a guy and why they work so well

It’s hard when you like a guy. You want to flirt with him but are either too nervous to pluck up the courage, frightened you’ll run out of things to say, or worried your conversation will end up boring. Maybe you come across as too friendly instead of flirty. But these flirty questions to ask a guy will put you on the right track.

Showing a guy your interest in him is a little nerve wracking. One of the less scary ways to do it is by striking up a flirty conversation with him. You don’t have to be too forward or risky, just ask some silly, funny, flirty questions and see where the conversation takes you. More importantly, see if he starts flirting with you too.

If he responds in kind, then you know you are onto a winner. If he doesn’t, then it’s not too late to back out gracefully without feeling like you got too much egg on your face!

Should you text him these flirty questions?

Texts work really well! In fact, they may even work better for you if you think you may freeze up in person. Sometimes, we just feel a bit more courageous while lounging at home in the comfort of our own homes, and that makes it easier to flirt over text with a guy. It also gives both of you a few precious seconds to phrase your thoughts out and type them without getting stressed, which leads to more flirty banter.

When you like a guy, your mind is all over the place. You spend most of your time daydreaming and having panic attacks about him, and less time actually getting to know him. You’re worried he doesn’t like you or you’re too boring for him.

If he likes you back, that’s the last thing on his mind. So, instead of getting stressed, get to know what’s on his mind with a flirty question or two! And the easiest way to read is mind is by using these questions, and gauging his replies.

You’re probably not hanging out with him 24/7, but that doesn’t mean you can’t get to know him. Texting has its cons, but it’s also a great communication tool. Plus, some people feel more comfortable being honest and open over text than in person.

Sending some flirty questions can be a great way of getting to know him, while also seeing if you are compatible. Plus, if he flirts back, it’s fun. It’s time to start flirting with these flirty questions to ask a guy over text!

The better option: Flirty questions in person or over text?

Why not both?! That would definitely be the best way to do this. When you use these flirty questions to ask a guy in person, everything happens faster. He laughs, you laugh, he tries to hide his awkwardness, and your heart skips a beat, all in a matter of seconds. So if things really work out well, you two could be making plans for a date, five minutes into asking a guy any of these flirty questions!

On the other hand, texting him these questions gives you the courage you need, but it’s way slower. You two could be flirting back and forth for days without either of you making a real move to ask the other person out. Sometimes, it just works because you two could build a lot of sexual chemistry by them.

At other times, the flirty conversations could just fizzle out. So use what works best for you, but never forget the end goal you have in mind – be it hooking up with him, or going out on a date with him. As long as you remember why it is you’re asking him these flirty questions, everything would go just perfectly!

If you’d like to get the message across more subtly, try these unique compliments for guys they’ll never ever forget! It gets the message across, without making it obvious you’re flirting with him.

The very best flirty questions to ask a guy and make him flirt back with you

How do you ramp up the conversation so it’s flirty rather than friendly? You want to take that next step and give him an indication you like him, but how?

If you want to start a flirty conversation with a guy, you’re in luck. just use any of these flirty questions to ask a guy we have here, and you’ll definitely be able to get the message across!

1. Have I seen you here before?

This one works perfectly if you don’t know the guy yet. And this old ‘do you come here often’ classic is an obvious sign you want a flirty conversation.

2. How has a guy like you stayed single for so long?

Kind of a jab, guys are usually single for a while for a reason. If it is a broken heart, make it light. If he is a player, you will know because he probably comes back with a cheesy line that makes you think “what?”

3. Have you been working out?

Asking a guy this is obviously telling him you’ve checked him out, and you think he looks good!

Okay, it’s a little cheesy, but you need to look beyond that. With this question, you’re saying, “I checked you out, I think you look fine as hell, and I want you to know it.” Whatever the reply, whether it’s a yes or no, you can automatically compliment them on their body.

4. Is it difficult to be so hot?

Yep, ask him a question while telling him what you think of his good looks!

5. How fast did you have to run to get away from the herd of girls chasing you?

Find out if he is a serial monogamist or a serial player. He might give up the truth… you just never know. Even if he’s surprised, he can’t help but blush and run out of words for a few seconds!

6. Are you trying to turn me on or are you just that irresistible?

Chemistry is not something that two people always mutually have. If you ask him this question, you know immediately by the look on his face if he is as attracted to you as you are to him.

7. Is it hard to be so wanted?

Sarcastic and simple, yet, to the point!

8. Do you have a carry license for those guns?

So cheesy, but guys are just vain enough for it to work! This is just about the oldest and corniest thing to say as you wrap your hands around his big biceps. But, for the shy guy who isn’t used to come-ons, it definitely makes him smile at your ridiculousness and lets him know you are okay with putting your pride on the line.

12. What’s your idea of the perfect first date? Do you think I’d like it?

This is a funny, yet perfect, way to get him to talk about dating you. You ask the question, but he’ll be the one coming up with ways to impress you. See, you can turn the tables around with the right kind of flirty questions to ask a guy!

13. What do you think is your most attractive feature?

If you’re talking to a guy who’s awkward or not the brash kind, this is a great way to get him to open up and brag about himself.

14. What do you think is most attractive about me?

Does he think you’re hot? Does he think you’re cute? What catches his eye most about you? Getting to know this can help you understand how he sees you.

15. You totally surpassed my friend zone, have you considered taking it to the next level?

If it is someone who you have been friends with for a while and is also your secret crush, this question just might take it to the next level and turn the heat up in your “friendship.”

16. I can feel the chemistry between us, do you feel it too?

One of the most poignant yes or no flirty questions to ask a guy because he’s stuck with telling you the truth.

17. What was the first thing you noticed about me?

This is a perfect flirty question to ask a guy because he can’t hide the emotions in his eyes when he answers it. If he’s really into you, you’ll see his eyes shine as he talks about what he fell for.

18. Do you have anything blue to wear?

“If so, you would totally match my bedroom.” Just say it with a smile and a wink!

19. What do you think you would like better, dessert after dinner or breakfast in bed?

If you are looking for a one night stand, then this is the perfect way to say, “It’s on!”

20. If I said yes, what would you say?

Let him know your interest and find out if he’s cheeky enough to ask the right flirty question back to you!

21. Do you look this hot in the morning?

“I would like to find out tomorrow… what do you say?” Two questions in one, this is the perfect hook-up question to put him on the spot so that he can get your spot.

22. Is it the alcohol talking or did you say you would like to take me somewhere else?

You don’t want to put words in his mouth, but desperate times call for desperate measures, no? [Read: Surefire ways to find a one night stand and get them in bed]

23. Do you like breakfast in bed or going out to grab it tomorrow morning?

It’s subtle, but he’ll know what you mean! And you get to know right off the bat if you are having breakfast in your undies or hitting the nearest coffee shop in the morning.

24. Are you happy to see me or happy to see me?

Don’t give him a choice, make it for him.

25. Heads or tails?

He’ll ask you what’s the question. And all you need to do, is get close to his ear, and whisper, “anything you want with me!” and graze your lips against his ear lobe.

26. Are you trying to get me drunk to get me into bed?

This is a flirty question to ask a guy, especially if he asks you if you want another drink. It’s funny, and puts him in a spot. And if he’s embarrassed, all you need to say is “of course, I want another drink!”

27. Do you like sleeping on the right or left side of the bed?

Whatever he says, just say you like the other side. He can’t help but imagine you in bed with him!

28. You don’t snore, do you? I’d like to get some time before work in the morning.

Let him know that you plan on spending your night losing sleep with him.

29. Your place or your place?

Cute, flirty, and very sexy and upfront! And the bonus of making sure he doesn’t know where you live!

30. Are you always this hot or do you have a fever?

Cheesy, but sometimes those silly ones work, why not give it a try? Especially if you run your hand against his body as you ask him this flirty question!

 31. What’s your sign – taken, single, or available for the night?

If you want to ask if they are attached or actively looking, this outrightly sexy phrase lightens the moment and gets the message across!

32. Do you have a girlfriend?

This question is pretty forward but it lays your cards on the table. It makes it pretty obvious to a guy you want to be more than just friends, right from the outset. Not only will this question save you a lot of time from guessing his relationship status, but it’ll also lay your feelings on the table. The only reason why you want to know this is because you like them.

33. Did you know when I think of you it makes me smile?

This question will always make anyone blush. It’s a flirty question, but it’s extremely sweet and innocent. And if he’s someone who does make you smile, well, he’s worth keeping around.

34. Do you like me?

It’s forward, but you need to know. There’s no point waiting around for him to confess his feelings or string you along. If you’ve been flirting with him and you’re ready to take the next step, ask him if he likes you.

35. Should I be fearful? How many hearts have you broken already?

This works especially well if a guy tells you he likes you. You can let him know you’re interested, while making it clear to him that you’re wary of his intentions at the same time.

36. Are you free on…?

All you need to do is add the date and time. This is a forward way of asking a guy out, and good for you if you do it! We’re women and we’re free and powerful, it’s time to take control over your love life!

37. Do you prefer cuddling up or having a make-out session?

Putting pictures in his head of what it might be like to cozy up to you or to lock lips is a good indication you like him and want things to get flirty.

38. Are you a cat or a dog person?

Everyone knows if you ask this question it’s because you want to find out whether you are compatible. You may think it’s a silly question, but it’s not. Cat and dog people are pretty different. Maybe they hate cats, but you love them. What are you going to do?

39. What are you looking for in a partner?

Well, you do like him, right? Then this is an important question to ask yourself. What is he looking for in a partner? Listen to his answer carefully because you’ll want to know if you have what he’s looking for.

40. Why don’t you tell me more about yourself?

This is a little bit subtler but is still a flirty question to ask a guy because it demonstrates your interest in him and the fact that you would really like to get to know him better.

41. Is the way to your heart through your stomach or do you have another route?

Yep, put it all out there!

42. Am I the kind of girl you take home?

Girl next door or freak in the bed? He only finds out for sure by giving it a try.

43. If you put me in a cab, will you give the cab driver my address or come along?

If you had a few too many and want to know which way the night is heading before your last night cap, try this one out.

44. Did you believe in fate when we met each other?

Can’t believe that your heart strings are being pulled so hard? Let him know.

45. What’s the best kiss you’ve ever had?

Asking a guy to reminisce about a hot kiss that he’s had will turn his mind to sex. Or perhaps you kissed already and you hope that he says you?!

46. Have you ever had sex in an interesting/funny/risky place?

Again, turning the conversation to sex tells him that you like him and are interested in finding out more about his sexual history. If he’s up for revealing things about himself and asks you the same, it looks like some serious flirting is about to begin!

47. What’s your type?

Now find out what he goes for, is it you? This is one of those flirty questions to ask a guy that’s perfect to let him know you’re interested. If he’s interested in you, he’ll be sure to include many traits he sees in you. And if he isn’t into you, you’ll know in a minute, won’t you?

48. What do you find hot in a girl?

If he starts describing you, you know you are onto a winner!

49. How can you be single?

You’re obviously tell him that you think he’s great and would sweep him right up off that singles shelf in a heartbeat.

50. How did you get to be so cute?

This question is cute and flirty without being too forward. If he likes sweet and cheeky girls, he’ll love the compliment and give you one back right away!

51. Do you think about me when we’re not together?

Asking him whether he ever thinks about you is an easy flirty question to ask a guy and get him to flatter you and make you feel great.

52. What’s your ideal date?

Get him to think about dating and hopefully he’ll picture you there with him.

53. Are you busy on… ?

This is a good way to get him to ask you out without being too direct.

54. What does love mean to you?

This is a heavy question, so don’t use this right away. Ideally, you’d use this during a deep conversation when you feel comfortable enough talking about this. But it’s an excellent way to see how they see love and will point you in the right direction.

55. What’s your biggest sexual turn-off?

There’s something that makes him cringe; everyone has a turn-off. What’s his biggest turn-off? It’s a good way to get him talking dirty while revealing his turn offs at the same time.

56. Are you a cuddler?

If you’re someone who likes cuddling, you need a partner who’s into it as well. You can’t be cuddling yourself; it doesn’t work that way. This question is cute, but it also lets you know if you’re compatible with him.

57. What’s your stance on a girl making the first move?

Here you pretty much tell him you’ll make a move on him if he wants you to. It’s also an easy way for him to let you down if he doesn’t feel the same way.

58. Do you ever get shy around me?

If he does, he’ll probably blush and stutter. It will be oh-so-adorable!

59. Do I make you nervous?

This is the same sort of question. If he says yes, tell him he makes you kind of nervous too.

60. What turns you on when you see a girl?

If you want to be a bit forward, turn the conversation to sex and see where it takes you. If he likes you, he’s definitely going to say something that you know you have!

61. What turns you off about a girl?

Knowing the kind of things that turn him off will no doubt be useful later!

62. Where do you like to be kissed?

Okay, of course, the mouth is one place, but is there somewhere else? Maybe he loves being kissed on the neck, or maybe having his earlobes kissed, or perhaps he’s one of those guys who like it when a girl kisses him all around his lips. Wherever it is, you need to know the spot.

63. Describe yourself in three words. Be honest!

If you want to have a better idea of who he is, ask him to describe himself. It’s not an easy question to answer if you’re doing it honestly. 

64. Are you attracted to me?

If you want to be flirty but also want answers, this question goes straight to the point!

65. What do you wear in bed?

This question will bring up some naughty feelings inside the two of you and may even lead to sexting. Asking him what he wears to bed is a clear, “I want to see what you wear to bed” text. So, be prepared for a naughty reply.

If he responds with something normal, tell him you sleep naked and see what his response is!

66. Do you want to go out with me?

If you are the kind of girl that doesn’t like to beat around the bush, why not just ask him out already?!

67. Do you fancy me?

Ask him if he’s attracted to you—go on, we dare you!

68. Have you ever had a dream about me?

This cute question is a fun way to find out if he has you on his mind a lot. And if it’s a sexy dream, all the better!

69. Have you ever had a sexual fantasy about me?

Asking about his fantasies seems personal, but it’s a sure-fire way to know if he’s got the hots for you too. If he says yes, ask him what it was. That’s a pretty big piece of information you have in your hands. And maybe if he’s lucky, you’ll fulfill his fantasy.

70. Do I make you smile?

If he tells you that you make him smile, or even happy, he obviously crushes on you big time.

71. Do you know that you make me smile when I think about you?

Watch his body language to clue if he likes you back or not.

72. Are you shy around me?

If he gets shy around you, chances are, he fancies you.

 73. What’s your favorite position?

Find out what his favorite positions are in the bedroom and perhaps you can impress him later. Maybe he’s a fan of the classic missionary, or maybe he likes it a little naughtier. It’s a good question to see what he’s sexually into and if you are compatible. Plus, now you know his favorite position.

74. What’s the craziest thing you’ve done in bed?

See how wild he can be! Who knows, maybe this guy is a little wilder than you thought. Either way, it’s a flirty question to ask a guy that always gets a story started.

75. What’s your favorite part of sex?

Everyone has a favorite part of sex. Maybe it’s the makeout session or the part right before you have sex. See what part of sex he’s interested in the most, and of course, get his mind focused on a little fun in the sheets.

76. Where’s your favorite make-out spot?

Find out and suggest you go there pronto!

77. What do you value in a relationship?

See if you are compatible by finding out what’s important to him in a relationship.

78. What do you like about me?

Open the door for him to give you compliments. Then sit there and bask in the glory!

79. What’s your ultimate sexual fantasy?

Find out what he’s always wanted to do, and then make his dreams come true.

80. What excites you?

Find out what his passions are *not just sexually*. It leads to a bonding conversation and makes him feel more connected to you.

81. What are your dreams?

Find out if you dream about the same kind of future—hopefully one together!

82. Do you think you know what I want in a guy?

This is a way to get him all flustered. Then you tell him exactly what you want – Him!

83. What turns you on about me?

There’s something about you that he wants to have, and you need to figure out what it is. Maybe your smile turns him on or the way you laugh. Either way, now you know what features to emphasize around him.

84. Can you take care of me if we ever went out on a date?

Make him feel all manly and protective by playing the damsel in distress.

85. If we went on a date, where would you take me?

Getting him to imagine himself on a date with you increases the chances of it happening for real! Let’s see how romantic this guy really is. Ask him where he would take you out on a date. Is it somewhere special? Would he go out of his way for you?

So, next time you see your crush, and you feel ready to try some flirting, use the questions from this list. You’ll have a fun, flirty conversation going in no time at all!

Sometimes guys are slow on the uptake. If you aren’t someone inclined to make the first move, then these flirty questions to ask a guy might be the best way to covertly let him know that you have him in your mind. Depending on your comfortability, go the joking way or the “bring it on” way. It is all a matter of how far you want to take it and how interested you really are.

Use one of these flirty questions to ask a guy to get him to laugh, lighten his mood, or find out what he is thinking. If you want to know if there’s some chemistry between you two, these questions will get you the answers you crave.

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