Flirty Questions To Ask Your Crush

Flirting is an art—and sometimes, all it takes to spark a real connection is asking the right question. Whether you’re trying to break the ice, keep the conversation fun, or simply show your crush you’re interested, a flirty question can go a long way. From sweet and playful to bold and cheeky, the right words can make them laugh, blush, or think of you a little differently.

In this article, we’ve rounded up the best flirty questions to ask your crush—whether it’s a boy, a girl, or even over text—to help you turn casual chats into exciting, memorable moments.

RELATED:

Deep Questions to ask your Boyfriend

Table of Contents

Cute Flirty Questions to Ask Your Crush

What’s your idea of the perfect date?
Do you like it when someone makes you blush?
Who usually texts first—you or me? 😉
What’s the sweetest thing someone could do for you?
Do you think I’d make a good cuddle buddy?
What’s your favorite way to be spoiled?
Have you ever had a crush on someone like me?
What’s one thing that always makes you smile?
Do you think we’d look cute in matching outfits?
Who would win a staring contest—me or you?
Do you secretly like cheesy compliments?
Would you rather have me cook for you or surprise you with dessert?
How would you feel if I called you “mine”?
Do you like hugs that last a little longer?
Would you dance with me, even if there’s no music?
What’s the most romantic thing you’ve ever imagined?
Do you believe in love at first sight—or should I walk by again?
Would you share your fries with me, or am I too special for that?
Do you like hand-holding in public?
Who would fall asleep first on a movie night—me or you?
What’s your secret way of showing someone you like them?
Do you think I’d look good in your hoodie?
What’s the cutest nickname you’d give me?
If we got caught in the rain, would you kiss me?
Do you like it when someone teases you?
What’s the most adorable thing about you (besides your smile)?

Who would be more competitive at games—me or you?
Do you like forehead kisses?
Would you take me on a surprise adventure?
What’s your idea of a perfect cuddle session?
Do you like spontaneous compliments?
Who do you think would get shy first—you or me?
What’s your guilty pleasure when flirting?
Would you let me win just to see me smile?
Do you think about me when you’re bored?
What’s one thing you’d love to do together that we haven’t yet?

Do you like late-night deep talks?
Would you save me the last bite of dessert?
Do you like being called cute—or should I pick another word?
Who would take more selfies—you or me?
Do you like slow walks or fast adventures?
Would you let me mess up your hair just for fun?
Do you like surprises, or should I just tell you my plans?
What’s your favorite way someone could show they like you?
Who would fall asleep first on FaceTime—you or me?
Do you like it when someone steals your hoodie?
What’s the cutest compliment you’ve ever gotten?
Do you think we’d be the “cute couple” people talk about?

Flirty Questions to Ask Your Boy Crush

Do you think I’d look cute wearing your hoodie?
If I dared you to kiss me, would you?
Who’s luckier—me for crushing on you, or you for having me crush on you?
Do you like it when a girl makes the first move?
What’s one thing about me that you can’t ignore?
Do you secretly enjoy when I tease you?
If I called you handsome out of nowhere, would you smile?
Do you think we’d win “cutest couple” if we dated?
Who would fall in love faster—me or you?
Do you like it when a girl plays with your hair?
Would you let me win an arm wrestle just to impress me?
What’s your favorite thing about flirting?
Do you like forehead kisses, or should I try something else? 😉
If I stole your hat, would you chase me for it?
Who do you think would text first—me or you?
Would you rather watch a scary movie with me or a rom-com?
Do you get nervous when I look at you?
Do you like it when someone compliments your smile?
Would you let me be your player two in video games?
What’s one flirty thing you’ve always wanted to try?
Do you like it when someone notices small details about you?
Who do you think would win in a tickle fight?
Do you think I’d make a good girlfriend?
If I texted you at midnight, would you reply?
Do you like spontaneous adventures—or cozy nights in?
Who would cave first in a staring contest—me or you?
Do you like it when someone saves you a seat next to them?
If I dared you to hold my hand, would you?
Do you like compliments whispered or said out loud?
What’s one thing you’d love for me to say to you?
Do you secretly practice flirting in the mirror?
Who do you think would blush first—you or me?
Do you like it when a girl plays hard to get?
If I asked you to teach me something, would you?
Do you like random good morning texts?
Who would win at karaoke—you or me?
Do you like being teased, or do you prefer compliments?
Would you share your fries with me or keep them all?
Do you like late-night walks or morning coffee dates?
Who would laugh harder at a bad joke—you or me?
Do you think I could make you blush on purpose?
If I dared you to take me out, would you say yes?
Do you like surprises or planning everything ahead?
Who’s the bigger flirt—you or me?
Do you like when someone steals your hoodie just to keep it?
If I said I’m cold, would you share your jacket?
What’s one thing you think I’d never guess about you?
Would you be brave enough to kiss me in public?

RELATED:

Flirty Questions to Ask Your Girl Crush

What’s your idea of a perfect date night?
Do you like it when someone calls you gorgeous?
Would you share your favorite playlist with me?
Do you secretly like when I compliment you?
Who would blush first if we flirted face-to-face—you or me?
Do you think I’d look good holding your hand?
What’s one thing that instantly makes you smile?
If I wrote you a love note, would you keep it?
Do you like forehead kisses, or should I aim lower? 😉
Would you rather a coffee date or a late-night walk with me?
Do you like surprises, or do you prefer hints?
If I called you “cute,” would you deny it or agree?
Do you enjoy playful teasing or sweet compliments more?
Would you ever let me win just to make me happy?
Who would fall asleep first on a call—you or me?
Do you secretly love cheesy pickup lines?
If I gave you flowers, which ones would you want?
Do you think we’d be the kind of couple people envy?
Would you rather go stargazing or dancing with me?
Do you like holding hands in public?
What’s your go-to flirty emoji?
Would you let me borrow your hoodie?
Do you like being called pretty, beautiful, or both?
Would you dance with me in the middle of the street?
Do you think I could make you laugh no matter what?
If I made you blush, would you admit it?
What’s the most romantic gesture you’ve ever imagined?
Do you like slow cuddles or spontaneous adventures?
If I texted you at midnight, would you answer?
Would you share your dessert with me?
Do you like compliments whispered in your ear?
Would you rather I send you memes or sweet messages?
What’s your favorite way to be flirted with?
Do you think I’d look good in your selfies?
Would you get jealous if someone else flirted with me?
Do you like when someone pays attention to small details about you?
Who would cave first in a staring contest—you or me?
Do you like being spoiled with attention?
Would you let me mess up your hair just to tease you?
Do you like romantic gestures in public or private?
Would you be okay if I called you mine?
What’s the cutest thing a crush could do for you?
Do you think I’d be a good date planner?
Would you let me take a hundred pictures of you?
Do you like cozy nights in or adventurous nights out?
Would you blush if I wrote you a poem?
Do you like flirty nicknames, or should I create one for you?
Who would laugh harder at bad jokes—you or me?
Do you secretly love long hugs?
Would you say yes if I asked you out right now?

Flirty Questions to Ask Your Crush Over Text

What’s the first thing you think about when you wake up?
If I sent you a wink emoji, how would you reply? 😉
Do you smile when you see my name pop up?
What’s your go-to flirty text?
Do you think I text too much—or not enough?
If I dared you to text me something bold, would you?
What’s your favorite late-night text vibe—funny or flirty?
Do you get butterflies when I text you first?
Would you rather I send you a cute selfie or a funny meme?
If I asked you to FaceTime right now, would you?
Do you ever reread my messages?
What’s your favorite emoji to flirt with?
Who would text back faster—you or me?
Do you get excited when I text you out of the blue?
What’s one thing you wish I’d text you more often?
Would you let me send you a good morning text every day?
Do you ever wait to see if I’ll text you first?
If I sent you a heart emoji, how would you respond? ❤️
Do you like when texts are short and sweet—or long and deep?
Would you send me a late-night “I miss you” text?
Do you smile at your phone when I text you?
What’s the flirtiest text you’ve ever sent?
Do you like when I double-text, or is once enough?
If I asked for a picture of you, would you send it?
Do you secretly screenshot my texts?
Who would text first after a date—you or me?
Do you like voice notes or just texts?
Would you stay up late texting me even if you’re tired?
What’s your favorite kind of goodnight text?
If I sent “guess what?” would you reply fast?
Do you like when I tease you over text?
Would you rather a random joke or a flirty compliment?
Do you think about me before replying to my texts?
Would you text me back if I just sent “👀”?
What’s your go-to goodnight emoji? 🌙
Do you like getting surprise flirty texts?
Would you text me if you missed me?
Do you think texting can be more romantic than talking sometimes?
Would you let me spam you with gifs?
Do you secretly wait for my messages before bed?
If I texted “I’m bored,” would you entertain me?
Do you like when texts are playful or deep?
Would you rather I call you or text you all night?
Who would fall asleep first during a late-night texting session—you or me?
Do you like unexpected compliments in the middle of the day?
Would you text me first tomorrow just to surprise me?
What’s one emoji you’d use to describe me?
If I asked you to send me your smile, would you?
Do you like when texts feel like mini love notes?
Would you answer “yes” if I texted, “Wanna go out?”

Deep Flirty Questions to Ask Your Crush

What’s the most romantic thing someone could ever do for you?
Do you believe in love at first sight—or should I walk by again? 😉
What’s your love language—words, actions, or touch?
When was the last time someone made your heart race?
Do you think I’d make a good date?
If you had to describe your dream partner in 3 words, what would they be?
Do you think timing matters in love, or is it all about connection?
Have you ever thought about what your perfect kiss would feel like?
Do you believe soulmates exist—or do we create them?
What’s one thing you’ve always wanted in a relationship?
Do you think emotional attraction is more powerful than physical?
What’s the sweetest thing a crush has ever done for you?
Would you rather fall in love slowly or all at once?
What’s your biggest turn-on that isn’t physical?
Do you think people meet for a reason—or just by chance?
If I asked you on a spontaneous trip, would you say yes?
What’s the one question you wish someone asked you in a relationship?
Do you think late-night talks make people fall for each other faster?
What’s the most thoughtful compliment you’ve ever received?
Do you believe in destiny when it comes to love?
What’s the biggest risk you’d take for someone you like?
Have you ever felt an instant spark with someone?
Do you think true love feels calm or exciting?
What’s one thing you secretly find attractive about me?
Do you think good chemistry can be built—or is it instant?
What’s your idea of the perfect first kiss?
Would you rather someone write you a love letter or plan you a surprise date?
What makes you feel instantly connected to someone?
What’s your most unforgettable romantic memory?
Do you think best friends make the best couples?
If you could only choose passion or stability in love, which would you pick?
What’s the deepest way someone has ever flirted with you?
Do you think falling in love should feel effortless?
What scares you most about opening up to someone?
Would you rather someone love you for who you are now or who you could become?
Do you think attraction grows stronger over time or fades?
Have you ever had a crush you couldn’t stop thinking about?
What’s one secret you’d only share with someone you really trust?
Do you think I’d make a good partner in the long run?
What’s the kindest gesture someone could do during a date?
Do you think you fall in love with people’s eyes or their soul first?
Would you rather someone listen to your heart or read your mind?
What’s one thing that makes you instantly think of romance?
Do you believe true love is rare or everywhere?
What makes you feel most cared for in a relationship?
Would you rather spend a night under the stars or by candlelight?
Do you think flirting can reveal how much someone cares?
What’s one dream you’d want to share with your future partner?
Do you think about the future when you like someone—or just the moment?
Would you let yourself fall in love if it felt right—even if it scared you?

Biju Debnath

Meet Biju Debnath, the founder and editor of Swag Captions. He started the blog in 2019 and continues to manage it to this day. With over 5 years of experience writing social media captions, he has been successful in making this blog the largest free Instagram Caption provider site in the industry.