Flirty Questions to Ask a Guy

Playful and Romantic Flirty Questions to Ask a Guy Anytime

BySophia Nguyen

Flirting isn’t just about butterflies in your stomach—it’s about sparking laughter, building connection, and keeping things irresistibly fun. Whether you’re texting late at night, sitting across from him on a date, or just looking for a playful way to turn small talk into sparks, the right flirty question can do wonders. Think of them as little conversation boosters—cute enough to make him smile, clever enough to keep him hooked, and (when the timing’s right) spicy enough to turn up the heat.

In this article, you’ll find the best playful and romantic flirty questions to ask a guy anytime—from funny icebreakers to cheeky late-night texts. Get ready to make him laugh, blush, and maybe even fall a little harder for you.

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Flirty Questions to Ask a Guy You Like

  • What’s the first thing you noticed about me?
  • Do you ever think about me when we’re not together?
  • What’s your favorite memory of us so far?
  • If I asked you to plan our next date, what would you do?
  • Do you like it when I compliment you?
  • What’s the one thing you wish I’d say to you right now?
  • Do you prefer when I call you cute or handsome?
  • If I wrote you a love note, would you keep it?
  • What’s your favorite thing about my personality?
  • What’s your favorite thing about my looks?
  • Do you think we’d make a good couple?
  • Have you ever bragged about me to someone?
  • Do you smile when you get my texts?
  • What’s one thing I do that you find adorable?
  • Do you like holding hands in public?
  • If I hugged you right now, how long would you hold on?
  • What’s the sweetest thing you’d want me to say to you?
  • Do you believe in soulmates?
  • If I were a color, what would I be?
  • Do you like it when I tease you?
  • What’s something you’ve always wanted to ask me but haven’t?
  • What song reminds you of me?
  • Would you dance with me even if no music was playing?
  • Do you ever wonder what I think about you?
  • What’s one thing you wish we did more often together?
  • If we went on a road trip, where would you take me?
  • Do you like it when I text you first, or do you prefer to chase me?
  • What’s one thing you want me to know about you that I don’t yet?
  • Would you ever write me a cheesy love letter?
  • If I dared you to tell me something sweet, what would it be?
  • Do you like it when I play hard to get?
  • What’s the cutest couple activity you’d want us to try?
  • Have you ever replayed one of our conversations in your head?
  • What’s one thing you’d never get tired of hearing from me?
  • Would you ever surprise me with flowers—or food? 🌹🍕
  • If I gave you a nickname, would you like it?
  • Do you want me to text you goodnight every night?
  • What’s one thing you think we’d be amazing at doing together?
  • Do you like cuddling or kissing more?
  • If I showed up at your house randomly, how would you react?
  • Would you ever write me into one of your dreams?
  • Do you think I’m crush-worthy?
  • What’s one thing you wish you could tell me right now?
  • Would you kiss me if I asked you to?
  • Do you like me more when I’m being silly or serious?
  • What’s one thing you’d love to do with me that we haven’t yet?
  • Would you ever want us to match outfits?
  • If I told you I liked you, what would you say?

Dirty Flirty Questions to Ask a Guy

  • What’s the first thing you notice about me when I walk into a room?
  • Do you like when I whisper in your ear?
  • If I dared you to kiss me right now, would you?
  • What’s the most attractive thing a girl can do?
  • Do you like it when I get a little bossy? 😉
  • What’s your favorite spot to be kissed?
  • Would you rather slow dance with me… or make out with me?
  • Do you like when I get flirty in public or private?
  • If I sat on your lap, what would you do?
  • Do you prefer sweet kisses or passionate ones?
  • What’s your idea of a “perfect night in”?
  • If I wore your hoodie and nothing else, would you mind?
  • Do you like when I tease you until you blush?
  • What’s one secret fantasy you’d never tell anyone but me?
  • Do you like playful biting—or is that too much?
  • What’s hotter: eye contact or a surprise kiss?
  • Would you like it if I sent you a flirty late-night text?
  • What do you think about when I flirt with you?
  • If I leaned in close, would you pull away or kiss me?
  • What’s something you’d love for me to whisper to you?
  • Do you like cuddling that turns into kissing?
  • If I challenged you to a “kiss marathon,” would you win?
  • Do you secretly like it when I make you nervous?
  • What’s the boldest thing you’ve wanted to do with me?
  • If I played with your hair, how would you react?
  • Do you like when I hold your hand… or grab your shirt?
  • If I asked you to rate my kisses, what would you say?
  • Do you prefer romantic touches or wild ones?
  • Would you want me to steal your hoodie… or your bed space?
  • Do you like it when I get a little competitive and flirty?
  • What’s sexier: my smile or my eyes?
  • If I kissed you right now, would you kiss me back harder?
  • Do you think I’d be a good kisser?
  • Would you ever let me win a game just to kiss me?
  • What’s hotter: a flirty text or a surprise kiss in person?
  • Do you like it when I lean close just to make you blush?
  • What’s the one thing about me you can’t stop thinking about?
  • If I whispered something naughty, how would you react?
  • Do you like it when I leave you wanting more?
  • If I said “prove you like me,” how would you do it?
  • Do you think I’d be fun to kiss in the rain?
  • Would you rather kiss me goodnight or good morning?
  • Do you like when I bite my lip while looking at you?
  • What’s hotter: playful banter or total silence with chemistry?
  • Do you want me to flirt with you more or keep you guessing?
  • If I dared you to steal a kiss, would you?
  • Do you like it when I take charge, or when you do?
  • What’s one thing you secretly wish I’d do on our next date?
  • Would you kiss me if we were stuck in an elevator?
  • What’s the wildest thought you’ve had about us?

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Flirty Questions to Ask a Guy Over Text

  • What’s the first thing you’d do if I showed up at your door right now?
  • If I texted “come over,” how fast would you get here?
  • What’s one emoji you’d use to describe me?
  • Do you smile at your phone when I text you? Be honest.
  • If I kidnapped you for a day, what would we do?
  • What’s your favorite late-night snack—and can I join? 😉
  • What’s your idea of the perfect date… and does it include me?
  • If I sent you a flirty selfie right now, would you save it?
  • Do you prefer sweet or spicy… in food and in girls?
  • What’s something you want me to text you more often?
  • If I were a song stuck in your head, which one would it be?
  • What’s the most romantic text you’ve ever gotten?
  • If I sent you “guess what?” how would you reply?
  • Would you rather a good morning or good night text from me?
  • If I dared you to flirt with me over text, how would you start?
  • What do you imagine I’m wearing when I text you?
  • What’s the cheekiest text you’ve ever wanted to send me?
  • If I gave you three words to describe me, what would they be?
  • Which text from me has made you laugh the hardest?
  • If we were texting late at night, would you fall asleep smiling?
  • Who do you want a text from right now? (Careful 😏)
  • Would you rather I text you something sweet or something spicy?
  • If I double-text you, do you secretly love it?
  • What’s the most distracting text I could send during your workday?
  • If I sent you a pizza and a flirty note, would you share?
  • Do you think about me before you reply, or do you just type fast?
  • If I said “text me something risky,” what would you send?
  • Which emoji makes you think of me instantly?
  • If I said “describe our date in emojis only,” what would it look like?
  • What’s the most fun conversation we’ve had so far?
  • If I texted “I’m bored,” what’s the first thing you’d say?
  • Do you prefer long convos or short, teasing texts?
  • If I sent you “guess what?” would you play along?
  • What kind of text would make you drop everything just to reply?
  • If you had to choose: a flirty text or a flirty call from me?
  • Would you save my texts if they made you smile?
  • If I texted “let’s go on an adventure,” where would you take me?
  • What’s something you want me to text you right now?
  • If you got a flirty text from me at 2 AM, what would you think?
  • Would you rather I text you first or make you chase me?
  • If I texted you “come outside,” would you?
  • What’s your go-to flirty reply when I tease you?
  • Have I ever sent you a text that made you blush?
  • Do you reread my texts? (Tell the truth 👀)
  • Which of my texts has been your favorite so far?
  • Would you rather I send a cute selfie or a flirty question?
  • If I said “send me a picture of your smile,” would you?
  • Which is more fun: my serious texts or my silly ones?
  • What would you text me if you wanted me to think of you all day?
  • If we played “truth or dare” over text, what would you dare me?

Funny Flirty Questions to Ask a Guy

  • On a scale of 1 to 10, how dateable do you think you are?
  • If I challenged you to a staring contest, would you let me win?
  • Would you still like me if I stole your fries on the first date?
  • What’s more irresistible—my smile or my sass?
  • If I dared you to sing me a love song, which one would it be?
  • Do you believe in love at first sight, or should I walk by again? 😉
  • If I was ice cream, what flavor would I be?
  • Would you trust me to pick our Halloween couple’s costume?
  • If I was a pizza topping, what would I be?
  • Do you think I could beat you at Mario Kart? (Spoiler: I can.)
  • If we were stuck on a desert island, would you still try to flirt?
  • Would you rather kiss me in the rain or kiss me after tacos? 🌮
  • What’s more dangerous: my eyes or my sarcasm?
  • If I challenged you to arm wrestling, would you let me win?
  • If I said “I’m cold,” would you give me your hoodie… or keep me warm?
  • Would you ever write me a cheesy pickup line?
  • If I stole your hoodie, would you actually ask for it back?
  • Do you think we’d win “cutest couple” if we entered?
  • If I asked for dessert, would you buy me cake or just kiss me?
  • Would you ever let me change your phone wallpaper?
  • What’s funnier—my jokes or the way you laugh at them?
  • If I was a cat, would you pet me or ignore me? 🐱
  • Would you let me beat you at trivia just to see me smile?
  • If we had matching pajamas, would you wear them?
  • What’s scarier: horror movies or my playful side?
  • If I dared you to send me a flirty meme, would you?
  • Would you rather a surprise hug or a surprise kiss from me?
  • If we had a prank war, who’d win?
  • If I said “guess my favorite thing about you,” what would you say?
  • Do you secretly love it when I tease you?
  • If we played “truth or dare,” would you pick truth… or dare?
  • What’s the funniest way you’d try to impress me?
  • If I said “let’s play 20 questions,” would you try to win or flirt?
  • Would you let me win a pillow fight—or would you fight back?
  • If we were in a rom-com, what would our “meet-cute” look like?
  • Which would you rather: me cooking for you, or us ordering pizza?
  • What’s funnier: my bad dance moves or my good comebacks?
  • If I said “you’re in trouble,” what would your reply be?
  • Would you ever let me rename you in my phone with a silly nickname?
  • If I texted you a GIF war, would you join or surrender?
  • Do you secretly want me to roast you or compliment you?
  • If I stole your phone, what’s the first thing I’d find?
  • Which would you rather: a romantic dinner or a food truck date?
  • If I dared you to send me your best selfie, would you?
  • Do you think you could out-flirt me?
  • If I made you laugh too hard, would you hold it against me?
  • What’s funnier: me tripping in heels or you trying to catch me?
  • Would you let me pick our couple TikTok dance?
  • If I sent you a corny joke, would you laugh or groan?
  • Do you secretly like it when I make you blush?

Spicy Flirty Questions to Ask a Guy

  • If I sent you a “guess what I’m wearing” text, what would you hope the answer is?
  • What’s hotter—teasing texts all day or a surprise kiss at night?
  • Do you like it when I bite my lip while looking at you?
  • If I leaned in close and whispered something daring, how would you react?
  • Would you prefer me in heels or in your oversized hoodie?
  • What’s one thing I could say right now that would drive you crazy?
  • If we were alone with no one around, what would you do first?
  • Do you like when I play innocent or when I show my wild side?
  • What’s your favorite “spicy” thing for a girl to do?
  • If I texted you at midnight, what would you want it to say?
  • Do you think I’d make a good tease?
  • What’s hotter—eye contact across the room or a whispered secret?
  • If I dared you to kiss me for 10 seconds, would you stop at 10?
  • Do you like it when I make the first move?
  • What’s the most tempting thing about me?
  • If I showed up at your place right now, would you let me in?
  • Do you like playful challenges, like “catch me if you can”?
  • What’s one thing you’ve imagined me doing that made you smile?
  • Do you like it when I surprise you with bold questions like this?
  • If I asked you to send me a flirty emoji, which one would you pick?
  • Do you think I’d be trouble in the best way?
  • What’s spicier—me whispering your name or teasing you in public?
  • If I sent you a wink emoji, what would you send back?
  • Would you ever kiss me first just to shut me up?
  • Do you like when I “accidentally” brush against you?
  • What’s the boldest thing you’d want me to say to you?
  • Do you like being teased or doing the teasing?
  • If I dared you to send me a spicy text, would you?
  • What’s the most daring thing you’d do with me on a date?
  • Would you like me better if I played hard to get—or gave in easily?
  • What’s one thing I do that makes you think “damn”?
  • Do you like secret flirty touches or obvious ones?
  • If I leaned in like I was about to kiss you, would you wait or close the gap?
  • Do you like when I mess with your hair—or your self-control?
  • What’s spicier—me teasing you all night or surprising you once?
  • Do you think I’d look better in red lipstick or lip gloss?
  • Would you ever let me win a bet just so I’d owe you a kiss?
  • Do you like it when I challenge you in a flirty way?
  • What’s your favorite “dangerously flirty” thing to do?
  • If I played truth or dare with you, which would you pick?
  • Do you like me better sweet or spicy?
  • What’s the hottest thing someone’s ever said to you?
  • If I dared you to steal a kiss in public, would you?
  • Do you secretly like when I drive you a little crazy?
  • What’s one thing you want me to try just once?
  • Would you let me surprise you with something unexpected?
  • Do you like subtle flirting—or full-on fire?
  • What’s spicier—me making you laugh or making you blush?
  • Would you kiss me differently if nobody was watching?
  • What’s the one thing I could do right now that would leave you speechless?

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