Flirty Questions to Ask a Guy

FLIRTY QUESTIONS TO ASK A GUYSo, let’s say you really like someone.  Maybe this is a Tinder someone.  Maybe this is a “friend of a friend” someone.  Regardless of how you found this guy, you’ve found yourself in the terrible position where you know you need to start getting your game on, but you don’t know how to start. It’s totally ok to feel a bit flustered right now.  What you really need is to have a proverbial “ace up your sleeve” when it comes to breaking the ice.  You could always wait for him to make the first move, sure, but why not do whatever you can to keep the conversation heading in a promising direction?

Do you want to ask something sexy, but not too naughty? Well, you can opt for good flirty questions to ask a guy you like. They are hot enough to get him thinking, but not so dirty that he might freak out.  We know there are guys who are into that, of course, but if you’re looking for advice on how to make a conversation take a turn for the hotter, you’re probably both a little on the shy side, right?  We’re not judging- everyone goes at their own pace!

Your goal here is to get to know your crush better, so you can a) decide if he’s worth your time, and b) exactly how awesome he is. You can’t get to know someone without asking a few questions, right?

Are you planning to make eyes at some handsome guy you really like? You will be the queen of all coquettes with a few funny daring questions to ask a guy. Read on for a little inspiration in fine-tuning your flirting techniques, perfect for a quick copy-paste into a chat or messaging service of your choice!  But remember:  Always be you.  Feel free to make these your own, and get that sultry “hey boy” voice just right for YOU!

Flirty Questions to Ask A Boy:  The Cutest

Flirty communication with a boy may be a real challenge for some. The problem is that all girls want to flirt, but coming up with the right questions and timing is often hard. If you feel frustrated because of the difficulties in choosing the words, check out these cute-yet-flirty questions:

  • If we could spend one day together, where would you want to go? You can choose any place in the entire world.
  • Do you think about me when I’m away?
  • What’s the most exotic dream you’ve ever had?
  • Would you ever go to a nude beach?
  • Let’s say you’re at work, and I can bring you one thing to make your day.  What is it?
  • What are your thoughts about “true love”?
  • If you could hook up with any celebrity, who would it be?
  • Do you like being called sexy?
  • What is the best part about being in a relationship?
  • Do you prefer cuddling up or having a make-out session?
  • What do you think is the most romantic song on the planet?
  • Is it hot in here, or is it just you?
  • What are your favorite nicknames/pet-names?

Really Good Flirty Questions to Ask a Guy You Like

When you like a guy, it can be difficult to communicate with him. Why? Well, you’re probably afraid of saying or doing something wrong. Here’s a little secret:  we’re ALL a little awkward, so forget your fears! Go in with some really good flirty questions, and if he’s totally freaked out, then it just wasn’t meant to be.

  • When you return home after a long day at work, how would you want to relax?
  • How would you react if I told you that I like you?
  • How would you describe me, in just three words?
  • Do you find tattoos sexy?
  • If you had no choice, how many days do you think you could abstain from sex?
  • What makes you feel sexy?
  • Would you ever send me a naughty picture?
  • Do you like to give massages or receive massages?
  • If you had a pair of x-ray glasses, what would you look at first?
  • What turns you on or off most about dating?
  • Tell me about your parents. Are they good looking like you?
  • What is something you would really like to do with a girl but are shy to admit?
  • Did you know that you make me smile?

Hot Flirty Questions to Ask a Boy You’d Like to Hit on

The beginning of new relationships will never be easy! As a rule, when you decide to hit on somebody, you face a whole minefield of anxiety and nervousness. What if I say the wrong thing?  What if I use the wrong words?  What if he’s just not that interested?  Here’s the thing, ladies:  you won’t know unless you ask.  You can either suffer through weeks and months of avoiding the issue, or you can go ahead and ask some hot flirty questions and get things going.  Besides… if he thinks you’re being weird, you can always just reply “Oops… that was for someone else.”

  • Where do you like to be kissed the most?
  • How would you react if I kissed you, right here and right now?
  • If we had only 24 hours to live, what would you want to do first?
  • Have you ever tried to picture me naked?
  • Have you ever wanted to role play?
  • So… are you more of an ice guy, or a wax guy?
  • What are your thoughts on lingerie?
  • Do you want to do it in a public place?
  • How would you like to spend an entire evening with me?
  • What is the most amazing place you’ve ever had sex?
  • Does the thought of recording a video turn you on?
  • What attracts you to a woman?
  • Do you like dirty talk?
  • How do you not spend all day looking in the mirror?

Samples of Personal Questions to Ask a Guy You Like Over a Text

Sure, talking to someone either in person or over the phone is MUCH more intimate than texting them.  But hey, this is the 21st century, and practically the only way to reach someone is via some sort of chat, text, or messaging system.  Besides, there’s something inherently sexy about building up the tension over text, and it keeps you from getting too nervous when you finally meet in person!

  • Is there something crazy that you’ve ever dreamt of doing, but never got the chance to do it?
  • What type of flirting do you prefer – via texts or face to face?
  • What is one thing that gives you butterflies?
  • Do you see me in your future?
  • Have you ever had sex on the beach? No. I don’t mean the drink.
  • Have you played with any toys recently *wink*?
  • Personally, do you think size matters in reality?
  • What do you like to wear to bed?
  • Do girls who make the first move intimidate you?
  • What is your perfect idea of a date?
  • Have you ever had a dream about me?

Best Random Questions to Ask a Guy You’re Crazy About

Do you know what is the best way to know something about a guy you like and make him get interested in you at the same time? A little game of “Random Truths” should get things going.  Basically, it’s like Truth or Dare, only there’s no dare option… the questions are daring enough! The idea is to start out with something really benign, like “what’s your favorite breakfast?” and then work your way up to one of these thought-provoking topics!

  • What’s your opinion of love at first sight?
  • Which 3 things are the most important in a relationship for you?
  • What do you think is your best physical feature, and why?
  • What do you think is my best physical feature, and why?
  • How do you feel about kissing in public?
  • Who should make the first move in a relationship?
  • If you could change one thing about your life right now, what would it be?
  • Have you ever been caught naked by someone?
  • Have you ever had a secret crush on any of your teachers or friends, and have they ever got to know about it?
  • Ever been in love with 2 people at the same time?
  • What’s your most embarrassing moment?
  • What are you looking for in a girl?
  • What was your reaction when you first saw me?
  • What’s the worst text that you accidentally sent?

Get His Attention with These Funny Daring Questions to Ask a Guy

Sometimes, a conversation can hit a brick wall.  Maybe this lull has gotten super frustrating.  In that case, it’s time to spice things up with some daring questions.  These may seem brazen at first, but there will be a time when pulling out one of these questions will head the conversation into the next dimension!

  • What was the first thing that came to your mind when you saw me? Why?
  • Are you always this interested, or is this level of interest just with cute girls like me?
  • Hot showers or bubble baths?
  • Glass of wine or 6 pack of brews?
  • Which is the first region your eyes would wander to if you were to ever see me naked?
  • If I’m feeling horny when you’re around, do you think you’d realize it? And how do you think you’d recognize the signs?
  • If you had to have a sex change, what part of your body would you want enhanced more than anything else?
  • What gets you more excited, faster, phone sex or sexting?
  • While having sex, would you prefer getting on top or staying down in bed?
  • What’s the farthest you’ve gone on a first date?
  • What does your ideal girl look like?
  • What’s your idea of a perfect kiss?
  • How can someone like you be single?
  • Are you a boob man or a butt guy?

Interesting Flirty Questions to Ask Your Crush Over a Text

Are you sure that you are not good at flirting over text messages? You’re probably much better than you think, and besides- it’s quality over quantity. Take a look at some of these text-worthy questions to help inspire you to be your flirtatious best when talking to the man of your current dreams.

  • Do you like to be the dominant or submissive partner in a romantic relationship?
  • Have you ever flirted with a stranger online?
  • Tell me about the most embarrassing or awkward experience you’ve had around me *even if it’s silly* that you’ve never told me about yet?
  • If you had to pick an animal, which animal do you find the sexiest of all?
  • If the world froze for an afternoon and only you could move and no one could see you or remember what you did, what would you do?
  • If I fell into a pool of chocolate, would you lick me clean?
  • What’s more romantic, or sexy: cooking for someone or dancing with someone?
  • What do you think is one thing all men should do when dating?
  • What is your biggest fantasy when it comes to me?
  • What would you do if we were home alone naked together?
  • Guess what I’m wearing right now?
  • Do you think about me a lot?
  • What is the most interesting thing you have on you or near you right now? Send me a pic of it.

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