150+ Flirty Questions To Ask A Guy…If You Dare!

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Dare to try these Flirty Questions To Ask A Guy?

So you’ve got your eye on a guy! He’s cute, he’s funny, he’s charming – how do you make him notice you? You’ve gotta up the flirt and get him to know you’re into him!

These flirty questions can help you figure out if he’s into you or not, with how he responds or acts when answering some of these questions.

text reads "flirty questions to ask a guy" and shows a man kissing a woman's cheek as she laughs.

But telling a guy that you’re into him outright and upfront isn’t always the best move. Sometimes being too upfront can scare him off. So our suggestion? Flirt it up! 

You can drop your crush some hints that you are interested by asking them some flirty questions for your crush. Not only will this drop a hint, but it can also give you an inclination as to whether or not they are interested in you back.

If they seem flirtatious back, that’s a great sign! If the conversation is a dud, you know it’s time to move on.

If you’re already in a relationship, try these flirty questions to ask your boyfriend.

Flirty Questions To Ask A Guy

Here are 150 flirty questions that you can ask a guy to find out if he’s interested:

  1. What physical features are you most attracted to in a girl? (This opens up the floodgates to allow him to compliment you and your attributes).
  1. What do you look for in a potential girlfriend? (This allows you to see if you’re a good fit for what he’s looking for)
  1. What do you like to do in your spare time? (Maybe he’d like to do something with you sometime?)
  1. What does your dream date look like? (Maybe you can dream together)
  1. What would you take a girl to do on a first date? (This opens up the opportunity for him to ask you on a date).
  1. What’s your favorite ice cream flavor? (This opens up the opportunity for him to ask you to go for ice cream)
  1. What do you think about Public Displays of Affection? (This will help you determine if you’re compatible).
  1. Do you believe in love at first sight? (Hopefully he’ll say “I do now that I met you”)
  1. What’s your sign? (If you believe in astrology, you can then compare your astrological compatibility).
  1. Who’s your celebrity crush? (Maybe they’ll say someone who resembles you!)

  1. Do you believe in soulmates? (This can help to determine whether you think similarly)
  1. If you were stranded on an island, what 3 things would you take? (Hopefully they say you!)
  2. Do you have any deal breakers in a relationship? (This will help you learn what they are looking for in a partner – and what they’re not).
  1. What’s your favorite movie? (A chance to bond over similar interests).
  1. Are there any movies in the theaters that you want to see right now? (This opens up the opportunity to ask you on a date).
  1. What does your perfect day look like? (Hopefully it involves seeing you at some point!)
  1. What’s the quickest way to your heart? (Make sure you take notes for future references).
  1. What’s your worst dating story? (This might not seem “flirty” but it will give the two of you a chance to bond over horror stories – we all have one)
  1. Do you have any couples that you aspire to be like? (This question can allow your communication to move to a deeper and more personal level).
  1. Do you believe in fate? (This can let you more into their head to learn how they feel about love and romantic relationships).

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  1. What’s your love language? (Again, take notes!)
  1. What are you most passionate about? (A question to learn more about who they are).
  1. What are you up to right now? (A super simple question that allows them to say something like, “wish you were here”)
  1. Are you a boxer or briefs kind of guy? (Starting to turn up the heat a little bit).
  1. Do you sleep in pajamas? Underwear? Or in your birthday suit? (Again, turning up the spice). 
  1. What are you wearing right now? (A classic) 
  1. What was your first thought about me? (Paving the way for some flattering compliments).
  1. Is there anyone you’re crushing on right now? (Hopefully they say you!)
  1. What do you think about marriage? (This question will help you determine if you’re on the same page, so that you can back out early if you’re not). 
  1. What are your thoughts on having kids? (Again, this helps you to see if you’re on the same page with what you want in the future. If you’re not on the same page, you might want to consider a friendship option). 

  1. Where do you see yourself in 10 years from now? (Another question to see if your goals are aligning).
  1. Are you close with your family? (A good chance to learn about their family values and to go a little deeper with your conversations). 
  1. Do you kiss on the first date? (Hint, hint!) 
  1. Do you like to text? (Offering him to ask for your number).
  1. Do you like to cuddle? (With any luck, the two of you will be cuddling soon!)
  1. Do you enjoy massages? (Maybe they’d like one from you)
  1. Describe the perfect kiss? (You might need this information in the future)
  1. How long into a relationship should you wait for “Netflix and Chill”? (Are you on the same page?)
  1. What’s your biggest turn-off? (Hopefully it’s not a habit that you have!) 
  1. What’s your biggest turn-on? (Note taken…)

  1. Tell me a secret? (Hopefully it’s saucy).
  1. I’m trying to decide what to wear tomorrow. What color do you think looks best on me? (Asking a man for their opinion will make him feel validated).
  1. Do you go for girls based on their looks or their minds? (Make sure he knows you have both).
  1. Are you a big spoon or a little spoon? (It’s important to know!) 
  1. What are you thinking about right now? (Hopefully he says you)
  1. How are you still single? (Let’s you know that you think he’s awesome and don’t understand why he’s not taken).
  1. How often do you like to be intimate in a relationship? (This can get his mind racing!)
  1. Truth or dare? (Now he can ask you some racy questions too!)
  1. Are you looking for a relationship? (Obviously, this is a must know. If you’re looking for commitment and he’s not, time to move on!) 
  2. What’s a great way for a girl to get your attention?

  1. What’s your favorite way to let a girl know you’re interested in her?
  2. What’s the first thing you notice about a girl?
  3. Do you have any fun questions you’d like to ask me?
  4. Do you consider yourself a romantic person?
  5. What’s the most romantic thing you’ve ever done for a girl?
  6. Describe what you would consider as “the most romantic date ever”
  7. What would you do if a girl was the one to make the first move?
  8. What tools do you think a couple needs to carry a relationship long term?
  9. What fictional character do you think I look like/remind you of?
  10. Now’s your free chance to ask me juicy questions. Any juicy questions you would like to ask me?

  1. What’s the most embarrassing thing that’s ever happened to you on a date?
  2. Do you think body language speaks more than words?
  3. Do you think we have fun conversation?
  4. What are your thoughts on a long-distance relationship?
  5. What’s the most important thing a girl can do to keep your attention?
  6. What’s your favorite memory from high school?
  7. Have you ever had a one-night stand?
  8. Are first impressions everything? What was your first impression of me?
  9. What’s the craziest thing you’ve ever done for a girl?
  10. What’s your dream job?

  1. Do you like receiving flirty texts? Or are they annoying?
  2. How do you think the two of us can build an even deeper connection?
  3. What’s the next level for us?
  4. What’s your favorite place to go when you need to reflect?
  5. If I was a flower, what kind of flower would I be and why?
  6. Describe the best kiss you’ve ever had
  7. What’s a fun way to make up after an argument?
  8. What’s the weirdest thing a girl has ever done in front of you?
  9. When was the last time you thought of me?
  10. How many text messages is too many text messages?

  1. If you could have a date night anywhere in the world, where would you go?
  2. What’s your favourite childhood memory?
  3. What’s the best compliment someone could possibly give you?
  4. What’s the best compliment you could possibly give someone else?
  5. Would you define yourself as a good kisser?
  6. What’s the weirdest place you have ever kissed a girl?
  7. Do you believe people can just be in the right place at the right time?
  8. In your opinion, what makes for great conversation?
  9. What’s the nicest thing someone has ever done for you?
  10. What’s at the top of your bucketlist?

  1. What’s the perfect way to ask someone on a date?
  2. Are the best things in life really free?
  3. What’s your favorite food?
  4. Are there any foods that if a girl ate in front of you, they would gross you out?
  5. What’s the easiest way to a man’s heart?
  6. What is it that you love most about your best friend?
  7. Do you think it’s important for your partner to be your best friend?
  8. Describe your best bedroom experience?
  9. What’s a playful way you let girls know you’re interested?
  10. Do you have a favorite  book?

  1. Do you think fairy tale endings happen in real life?
  2. What’s your secret weapon to attracting girls?
  3. Are you more than just good looks? Show me.
  4. Do you have an open mind when it comes to open relationships?
  5. Do you think you’ve mastered the art of flirting?
  6. Will you kiss a girl you like anywhere at any time, or does it need to be the right moment?
  7. What tv show best reminds you of us?
  8. What’s your best body part?
  9. What’s your favorite body part on a girl?
  10. Any chance you have a new crush in your life?

  1. How would you let someone know if you had a crush on them?
  2. From your past experience, what’s a quality you would never want in a partner?
  3. What’s the hottest thing a girl can do?
  4. What’s your favourite type of date? Adventurous? Staying in? Simple? Outdoors?
  5. How do you know if you really like someone?
  6. How do you know if it’s turned from like to love?
  7. What would girls classify as your sexiest personality trait?
  8. What would your ex say about you?
  9. What’s your favorite song to blast in the car?
  10. Do you sing in the shower?

  1. What’s a good wedding song?
  2. What’s your guilty pleasure?
  3. Would you change anything about your life right now?
  4. Would you prefer a double date? Or solo date?
  5. Do you prefer to hang out alone or in groups?
  6. When you’re in a serious relationship, what are your boundaries?
  7. Are you the type to give a girl your jacket if they’re cold?
  8. Are you a camping guy? Or do you prefer living in luxury?
  9. Have you ever stalked someone on social media?
  10. Dirty talk – do you wash your feet when you shower?

  1. What would be your go to topic for meaningful conversations?
  2. If the day were 5 hours longer, what would you do more of?
  3. Are you a morning person or a night hawk?
  4. Have you ever taken the day off just to snuggle in bed?
  5. What’s something you couldn’t go a full day without?
  6. What should a girl do for you everyday to keep you interested?
  7. Are you a giver or a receiver?
  8. Do you believe in parallel universes?
  9. If parallel universes are real, what would your ideal universe look like?
  10. If you could design a girl, what traits and qualities would she have?

  1. What’s something that you could work on in relationships?
  2. What’s the strangest fact that you know?
  3. It’s a zombie apocalypse. What’s your strategy?
  4. What job do you think I would best be suited for?
  5. If you had to get a full body tattoo, what would it be of?
  6. If you could erase any one thing from existence, what would it be?
  7. If you could clone anyone in the world, who would you clone and why?
  8. Do you believe in forever, lasting love?
  9. Do you believe in cryogenics?
  10. Do you think love exceeds time?

Of course, guys aren’t always good at taking a hint. So sometimes we just need to be a little straightforward:

  1. Would you like to take me on a date? 

Asking questions like these can lead to flirty banter and  be an excellent way to deepen a connection and spark a romantic interest with a guy. By engaging in playful and intimate questions and conversations, you not only get to know him on a deeper level but also create a fun and flirtatious atmosphere. 

It’s important to remember to be confident, respectful, and attentive to his responses. Whether you’re looking to start a new relationship or spice up an existing one, flirty questions can serve as a powerful tool to ignite chemistry and create lasting connections.

So go ahead and embrace your playful side, ask those intriguing questions, and let the sparks fly!

Sara, a seasoned expert in wedding planning and date ideas, brings a wealth of experience to our couples blog. With a background in the television industry and hands-on involvement in a dozen weddings, including working as a wedding assistant on "My Fair Wedding with David Tutera," Sara has an innate understanding of the magic that makes weddings truly special. Growing up with four sisters has given her unique insights into the dating world, making her a go-to source for practical and heartfelt dating advice. Her knowledge and enthusiasm make her the perfect guide for couples seeking to infuse their relationships with creativity and love.

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