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123 Flirty Questions to Ask a Guy You Like to Get Closer

Updated: Feb 24

Want to spice up your relationship with someone by bringing more fun and flirtation into conversations? Flirty questions help create lighthearted moments, reveal quirky personality traits and demonstrate your romantic or intimate interests. This article explores 123 enticing flirty questions ranging from charming to risqué that generate blushing, excitement and connection when talking with your crush, boyfriend, fiancé or husband. We'll also cover smooth ways to weave these questions into conversations depending on your flirting style and his responses. Let the fun begin!

girl asking flirty questions to a guy she likes, riding horses at carnival

123 flirty questions to Ask a Guy you Like to Get Closer and Make Him Blush:

Flirty Icebreaker Questions to Ask a Guy and Start a Conversation

Breaking the ice with flirty questions can feel nerve-wracking, so having some playful and charming flirty questions ready will get those butterflies fluttering in the right direction. These flirty icebreaker questions reveal his dreams, personality, and silly side in a lighthearted way.

Charming Flirty Questions

Start with gentle romantic flattery and appropriate playfulness. These sweet questions get him grinning and paint you as a thoughtful charmer:

  • If you could have any secret superpower, what would you choose?

  • Would you rather be able to read minds or stop time?

  • What embarrassing childhood habit have you never quite shaken?

  • Were you a troublemaker, teacher’s pet or shy kid in elementary school?

  • Do you have any hidden talents I don't know about yet?

  • What would your dream man cave or garage look like if money wasn't a factor?

Flirty "Would You Rather" Questions

These fun flirty questions to ask your crush provide amusing hypothetical dilemmas that reveal his preferences, wishes and personality:

  • Would you rather be forced to always tell the truth or always lie?

  • Would you rather get attention for your looks or your brain?

  • Would you rather be the funniest or smartest person you know?

  • Would you rather have super strength or super speed?

  • Would you rather fight one horse-sized duck or 100 duck-sized horses?

  • Would you rather give up your phone or give up your computer?

Playful Scenario-Based Flirty Questions

These flirty "what if" situations play with imagination in a charming way to uncover dating ideals, values and fantasies:

  • If you became famous overnight, who's the first person you would call and what would you say?

  • If you could learn to speak any language fluently tomorrow, which would you choose?

  • If you were a boxer, what song would you walk out to the ring to?

  • If you could join any band, what instrument would you play and what songs would you cover?

  • If they made a movie of your life, what actor would play you?

  • If you were stranded on a deserted island, what 3 things would you want to have?

Flirty Questions to Ask a Guy on a First Date and Get to Know Him Better

First dates are the perfect time for thoughtful flirty questions to ask your crush that provide glimpses into his essence. After you've got your fun date idea, disarm him with your genuine interest and don't be afraid to reveal your lovely flaws too. These flirty questions foster intimacy from the start.

Flirty Questions to Learn More About Him

Spark meaningful ideas on a first date by asking your crush:

  • What secret skills do you have hidden up your sleeve?

  • What's your biggest regret you've learned from?

  • What motivates you and drives your ambitions?

  • What accomplishment so far makes you proudest?

  • What's the most rebellious thing you did as a teen?

  • What habits or rituals from childhood have stuck with you into adulthood?

Flirty Questions About His Flaws

We all have lovely imperfections. Disarm him with vulnerability on a first date by asking:

  • What's your worst pet peeve?

  • Do you have any bad habits you want to fix?

  • What embarrassing thought have you never admitted out loud?

  • What's your worst quality?

  • What insecurity do you wrestle with? How can I help you overcome it?

  • What's your biggest weakness? How do you compensate?

Flirty Questions About His Past

Foster intimacy on your first date with him by better understanding who molded him:

  • Who has had the biggest positive impact on your life so far?

  • What's your most cherished childhood memory? Why does it stand out?

  • What title or superlative did you earn in high school? Class clown?

  • Were you more of a jock, nerd, artist, rebel or prep growing up?

  • What silly or reckless things did you do as a teen?

  • Who were your favorite celebrities or characters as a kid?

Flirty Questions to Ask Him to Keep the Conversation Going

Once you spark that initial chemistry and get to know your crush better, you’ll want to keep those sparks flying with more questions. Asking flirty questions to a guy you like about his interests, values, and desires demonstrates your eagerness to learn everything that makes him tick. These questions strengthen your bond and let him know your interested while keeping things fun.

Flirty Questions to Ask About His Uniqueness

Make him feel special with tailored questions highlighting his distinctive essence:

  • What secret skills or strengths give you an edge?

  • What's your most underrated or overlooked trait?

  • What sets you apart from other guys you know?

  • What talents or obscure knowledge do you possess?

  • What makes you wonderfully weird in the best way?

Playful Imaginative Flirty Questions

Spark fun daydreams and inject playful thoughts by asking him:

  • If you could visit any fictional world, where would you go? Hogwarts? Middle Earth?

  • What fictional hero or role model inspires you most?

  • What scene from a kids movie describes your ideal life? Flying house like Up?

  • If you could have any fantasy job, what would it be? Astronaut? Dragon trainer?

  • What fantasy adventure would you like to go on? Time travel? Atlantis exploration?

  • What fictional vehicle or gadget would be your dream toy? Batmobile? Iron Man suit?

Flirty Questions about His Passions

Tap into passions by asking fun flirty questions about his favorite music, movies, books, games, sports and hobbies:

  • Who's your favorite music artist and why?

  • What pumps you up song would you play to get motivated?

  • What guilty pleasure songs do you secretly love?

  • What book or movie scared you most? Why?

  • If you could star in any movie, what role would you play?

  • What hobby or skill have you always wanted to learn?

Imaginative "What If" Flirty Questions

Go on mind adventures together by wondering:

  • What if you woke up invisible tomorrow? What would you do?

  • What if you could become the president for a day? What laws would you pass?

  • What if you suddenly became a billionaire? How would you live differently?

  • What if gravity stopped working? Where would you float to first?

  • What if you could switch lives with someone for a day? Who would it be?

Don't forget to challenge him and respond with a little attitude every once in a while to keep things passionate!

Deep Flirty Questions to Ask a Guy You Like

At the right moment, don't be afraid to dive deeper emotionally with these deep flirty questions. Wondering about his passions, regrets and dreams creates bonds through vulnerability. Just remember to keep things balanced and follow up with funny flirty questions so you can bring out some humor.

Thought-Provoking Flirty Questions

To connect on a deeper level, ask flirty questions that demonstrate genuine interest in his inner self, passions and perspectives:

  • What cause or social issue inspires you to take action?

  • What are your top goals and ambitions in life?

  • What principles and virtues define your character?

  • What really matters to you more than money or fame?

  • How would you change the world if you had unlimited power?

  • Where do you look for wisdom and peace in life?

Flirty Questions About His Personality

Gain insights by asking:

  • Would you rather go on an introverted date or extroverted date and how does that look?

  • Are you a thinker who leads with logic or a feeler who follows emotions?

  • Would you say you're more passionate or practical?

  • What are your top strengths? Weaknesses?

  • Do you typically make decisions with your head or your heart?

  • Are you a highly sensitive person (HSP)?

Flirty Questions About His Dreams

Get him imagining by asking:

  • What would you do if you had unlimited money? Where would you live?

  • What would you spend your time doing if you could retire tomorrow?

  • If you could switch lives with someone for a day, who would it be?

  • How do you envision your life looking in 5 or 10 years ideally?

  • What topic could you give a 40 minute presentation on without any preparation?

  • What’s at the very top of your bucket list? How can I help you achieve it?

Flirty Questions that Show You Care

Demonstrate sincere interest in his inner life by asking:

  • What are you feeling most excited or happy about lately?

  • What worries or stresses you out these days? How can I help?

  • What always instantly cheers you up when you’re sad?

  • When do you most need extra motivation or encouragement?

  • What principles or virtues do you value most in life?

Flirty Questions to Light Him Up

Make him beam by asking:

  • When do you feel most like your authentic self?

  • What random things never fail to make you laugh or smile?

  • What activities bring you pure joy and excitement?

  • What makes you lose track of time because you enjoy it so much?

  • What was the last experience that filled you with inspiration?

If you can't seem to move past being friends, check out our post on breaking free from the friend-zone.

Funny Flirty Questions to Ask a Guy to Make Him Laugh

Laughter is needed in all relationships. Silly scenarios reveal his quirky side while absurd flirty questions catch him delightfully off guard. These random funny flirty questions will get you both smiling.

Goofy Flirty Questions

Make him laugh by asking silly absurdities like:

  • Would you rather have cheesy nacho fingers forever or sweat ketchup?

  • Would you rather be covered in fur or covered in scales?

  • Would you rather make everything you touch turn to Jell-O or cheese?

  • If you were a hot dog, what toppings would you want on yourself?

  • Would you rather have a dragon or a hippo as your eternal pet? Why?

  • Would you rather fight 1 horse-sized duck or 100 duck-sized horses?

Funny Questions to Catch Him Off Guard

Use these random funny questions to make him go "wait what..?":

  • How far into a watermelon can you stick your tongue?

  • What nasty smell can you not get enough of?

  • What's the naughtiest thing you've said to the mirror?

Flirty Questions to Ask a Guy Over Text

Texting opens up opportunities for playful flirting between in-person dates with flirty questions. Short, amusing questions tailored to texting builds excitement for the next time you’ll be together. These questions are perfect to ask your crush, boyfriend, fiancé or husband.

Questions to Send Him Over Text Message:

  • What is your perfect date night and describe it with emojis?

  • Do you want to facetime and see what I'm wearing?

  • Using an emoji, what do you want me to send you a picture of?

  • Which thumb did you use first to reply to this and don't think too hard?

  • Can you guess the first emoji that comes to mind when I think about you?

Check out these 93 flirty texts for him to make him want you if you need more ideas.

Hot and Steamy Flirty Questions to Ask Him

Once attraction is established, turn up the heat with racier flirty questions about desires and fantasies. Just make sure you have consent and avoid objectification. Naughty flirty questions can ignite new passion.

Forward Flirty Questions

Once rapport is built and you've seen his funny side, get bolder with direct flirtation:

  • On a scale of 1-10, how good of a kisser do you think you are?

  • Do you prefer kissing gently or passionately?

  • What’s the most public place you’ve gotten frisky in?

  • What’s the boldest thing you’ve ever done in public?

  • Have you ever flirted with a friend's girlfriend? Tell me about it.

  • What’s your best asset that you think makes girls flirt with you?

Flirty Questions that Hint at Sexual Chemistry

Turn up the heat by asking:

  • Do you like having your neck kissed or ears nibbled more?

  • Would you say you're dominant or submissive in intimate settings?

  • Have you ever gotten a sensual couples’ massage? Did you enjoy it?

  • Do you like having your hair played with or back scratched during intimacy?

  • What’s your top sexual fantasy we could role play together?

  • What’s your favorite intimate position?

Racy Flirty Questions

Once intimacy is established and you're ready to transition from funny to steamy, mix in some of these flirty erotic questions:

  • What’s the hottest dream you’ve ever had? Tell me details.

  • Have you ever gotten frisky in a public place? Where?

  • What clothing do you think I'd look sexiest in?

  • If I was your secretary, how would you want me to seduce you?

  • What's the most daring place you'd want to hook up?

  • What’s your favorite body part of mine?

Flirty Questions to Ask your Boyfriend or Husband

Even in long-term relationships, flirty questions help keep things exciting. Reveal new sides of each other through humor and thought-provoking discussions. For those who are in an established relationship, use these lively flirty questions to ask your boyfriend or husband:

Fun and Flirty Questions to ask your Boyfriend or Husband

  • If you could go on a romantic adventure with me back to any time period, where and when do you think you'd take me? And what would we do to make it unforgettable?

  • Imagine if we could talk to one type of animal.. which one would you want to have around so that we could add some humor into our lives and what do you think it would say?

  • If someone were to narrate our daily lives, what would they sound like and would it sound interesting? What do we do if it sounds like we need to solve relationship problems?

  • If we were to create our own unique romantic holiday tradition, what would it be and how would we keep the spark alive to make it special year after year?

  • If we were characters in a romance novel, what kind of thrilling adventures or passionate journey do you think we'd find ourselves in?

For more suggestions on communicating with your lover, check out our post on 7 creative ways to say I Love You.

How to Ask Flirty Questions Smoothly

Now you have endless flirty questions to ask your crush, boyfriend, fiancé or husband at your fingertips! Here are tips for integrating them into conversation charmingly:

  • Gauge his personality first. Is he outgoing or shy? Start slower if he blushes easily.

  • Weave questions in naturally by asking for clarification or stories related to topics he mentions.

  • Don't rapid fire questions. Let conversations flow and ask one intriguing question at a time.

  • If he seems uncomfortable with a flirty question, apologize and switch to small talk or humor.

  • Compliment him when he shares vulnerable stories and thoughts to build trust.

  • Monitor body language. Does he lean toward you or make extended eye contact while talking? If so, he's likely interested!

The most important thing is reading reactions to determine if your flirtatious curiosity is welcomed. Keep things light at first then gradually get bolder. If he comes back by asking you personal questions too, you're on the right flirty track!


With the right balance of charm, humor, intrigue and spiciness, the flirty questions to ask your boyfriend, husband, fiancé or crush will help you get to know him deeply while demonstrating a clear interest. Start with friendly questions then bring in racier ones to take it to the next level. Make sure you pay close attention to his comfort levels. Flirty questions can be a way to have a little fun and excitement, but they can also open the door to meaningful conversations.

You can learn more about him and gain his trust by showing you care about who he truly is. Learn the unique details that make him shine. Just be sure to avoid objectifying language or pressuring him. Your genuine interest and respect should be obvious.

So what are you waiting for? Keep these flirty questions around for inspiration at each stage of getting to know him. Then smile, take a deep breath and dive into playfulness that brings you both closer!

Make sure you check out our post on flirty questions to ask a girl you like to make her blush, which can also be used to ask a guy you like to make him blush!


Frequently Asked Questions

What are some good icebreaker flirty questions to ask your crush that are also funny?

Some funny and flirty icebreaker questions include asking things that catch him off-guard or make him feel embarrassed. Some examples would be asking about unwanted childhood habits he still has, silly "would you rather" hypotheticals, or off the wall things that don't make sense but makes him think.

How can I smoothly transition to deeper flirty questions to ask a guy?

Let conversations flow naturally and weave in deeper questions about his passions, values, dreams and personality when he seems engaged and open. Compliment him when he shares vulnerable thoughts to build trust and rapport.

What if he seems uncomfortable with a question?

Apologize if you notice him becoming uncomfortable and quickly change topics. Some people take longer to warm up to personal questions. Keep it light until you know him better. Monitor his reactions and body language for signals he welcomes your flirtatious curiosity.

How do I flirt with him over text?

Fun flirty text questions include asking him to describe a perfect date night in emojis or guessing what emoji he thinks of when he thinks of you. You can also ask him to facetime or see what you're wearing. Keep it playful but avoid sexting before establishing intimacy.

What are some sexy questions to ask a guy?

Once intimacy is established in person, you can mix in racier questions about turn-ons, fantasies and desires. For example, asking about favorite positions, public hookup spots, or what clothing he finds sexiest can ignite sparks. But avoid vulgarity or treating him like an object.

Should I ask these questions on a first date?

Save deeper and more intimate questions for when you know each other better, not a first date. Flirty questions help create connection, but move slowly enough for him to develop trust and feel respected, not objectified.

How do I know if he's interested in my flirty questions?

If he leans in, makes eye contact, asks you personal questions too or seems to enjoy revealing details about himself, these are signs your flirtatious curiosity is welcomed. Pull back if he gives short answers, gets distracted or acts disinterested.

What if he starts asking me flirty questions too?

If he reciprocates with personal flirty questions as well, it shows he feels the spark and wants to get closer too! Have fun bonding over playful answers and meaningful conversations that help you get to know one another on a deeper level.

Should I ask these flirty questions to my boyfriend if we're already in a relationship?

Absolutely! In established relationships, use flirty questions to spark escapist daydreams, laugh together about absurdities or learn new sides of each other. Keep the flame alive by asking about sexual desires, fantasies and romantic adventures.

How can flirty questions lead to meaningful conversations?

When you show genuine interest in his inner self, passions and perspectives, flirty questions can open the door to bonding over shared dreams, values and vulnerabilities. Make him feel special by highlighting his uniqueness too.

What are some romantic conversation starters with a man?

To ask about romance while starting a new conversation, think about what you perceive as romantic. For example, ask him where he would whisk you away to on a romantic getaway.

What are some sweet and seductive questions to ask a guy?

Try to ask a straight-forward one like what's your favorite way to be seduced. Or try to lead him in the right direction by asking what he thinks the best way to approach a romantic evening would be to get you in the mood. You can point him in the right direction if he gets it wrong.

How to initiate a flirty conversation with a guy?

Ask him what he finds cliché or boring when people start conversations with him. Get to know if he likes cheesy or stupid humor. You can use this information to know what to stay away from. Ask him what his go to icebreaker is when he's trying to start a conversation, or what is the best way to catch his attention when someone starts a conversation with him. These are all good ways to gauge what will grab his attention.


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