120 Flirty Questions You Can Ask a Guy to Get to Know Him Better

Flirty conversation is an art: you mix genuine curiosity with a sprinkle of tease so the talk feels exciting, not invasive. The right questions can uncover interests, values, and hidden talents—all while sending the message that you’re engaged and confident. These lists give you prompts for texting, first dates, late-night chats, or spontaneous voice notes. Pick a few, adapt the wording to match your style, and watch him open up while the chemistry builds.

Playful Icebreaker Questions

• What song instantly puts you in a flirty mood?
• If we were stuck in an elevator, what’s the first fun fact you’d share to pass the time?
• Which emoji describes you better than words ever could?
• What childhood crush taught you your best flirting skill?
• If you could rename yourself for one day, what smooth name would you pick?
• Which movie couple do you think we’d compete with for cutest chemistry?
• What’s your go-to “I’m interested” signal?
• If you had to impress me using only a snack, what would you serve?
• Which outfit do you secretly hope I notice first?
• What dare sounds fun but not too embarrassing for a first date?
• If your laugh were a flavor, what would it taste like?
• What’s the earliest memory you have of feeling butterflies?
• If we formed a duo name, what would it be?
• Which hobby of yours could you teach me in one hour?
• What’s one line you’ve wanted to use but never had the right moment?

Romantic Scenario Questions

• City rooftop picnic or hidden beach sunrise—where would you whisk me away?
• Which song would you slow-dance to in the living room lights-off?
• If we rewrote a famous love scene, which film would you pick?
• Candlelit dinner or stargazing road trip—what feels more “us”?
• How would you describe the perfect “just because” date?
• What small gesture makes you feel the most wanted?
• If you could freeze one moment of a relationship forever, which would it be?
• What quote sums up your idea of romance?
• How do you know when someone is worth chasing?
• Which season screams romance to you, and why?
• What scent reminds you of falling for someone?
• If we had a private getaway for 24 hours, what’s the first thing you’d plan?
• What’s the sweetest compliment you’ve ever received—and who gave it?
• How do you hint that you miss someone without saying it?
• What’s one bucket-list date you hope to experience this year?

Spicy “Would You Rather” Questions

• Would you rather share a secret playlist or your search history?
• Candle wax tease or ice cube chase—which challenge would you accept first?
• Whisper in the ear or cheeky text—what flirty move gets you quicker?
• Midnight swim or sunrise hike—where would sparks fly harder?
• Steal a kiss in public or write a love note in private?
• Slow tango or upbeat salsa—what’s your seductive dance style?
• Play truth or dare for an hour or never break eye contact for five minutes?
• Compliment my eyes or my mind first?
• Surprise weekend trip or surprise home-cooked dinner?
• Share dessert from one spoon or toast with two straws in one drink?
• Movie marathon under blankets or drive with the windows down singing loudly?
• First kiss on a ferris wheel or during a rainstorm?
• Exchange hoodies or swap playlists—what’s more intimate?
• Laugh until we cry or talk until sunrise?
• Leave flirty notes all week or one grand romantic gesture?

Deep Flirty Questions

• What quality in a partner makes you feel safest to be vulnerable?
• When did you last feel truly seen by someone?
• What fear would you face if I promised to hold your hand the whole time?
• Describe love in three words that aren’t “I love you.”
• How do you balance independence and closeness in a relationship?
• What personal goal feels easier when you imagine someone cheering you on?
• Which childhood belief about love do you still carry?
• How does someone earn your trust after a bad day?
• What song lyric hits harder when you think about falling for someone?
• If feelings were colors, what shade would you paint right now?
• What habit of yours becomes instantly softer around someone you like?
• Describe the moment you realized attraction goes deeper than looks.
• What part of your future feels brighter when you picture sharing it?
• How do you show affection when words fail?
• Which compliment would mean more from me than from anyone else?

Fun Teasing Questions

• On a scale from 1 to forgetting your phone passcode, how distracted do I make you?
• What pet name would you give me that’s sweet but slightly embarrassing in public?
• If confidence were a game, what’s your secret cheat code?
• Which flaw of yours do you secretly hope I find cute?
• When you think you’re being mysterious, what obvious clue do you leave behind?
• What’s your guilty-pleasure song you’d only sing if I promised not to tease—too much?
• Who wins in a pillow-fight: you or me? Defend your answer.
• What meme perfectly captures your flirting style?
• If I dared you to send me your most used selfie face, what would I see?
• Which emoji do you overuse when texting someone you’re into?
• What’s your go-to lie in Two Truths and a Lie?
• If I challenged you to one arcade game, which would you pick to impress me?
• What’s the most ridiculous thing you’ve done to get someone’s attention?
• When you try to play it cool, what tells on you first?
• If we both forgot our wallets on a date, what charming trick would you pull?

Text-Friendly Flirty Questions

• What’s your phone screen wallpaper—and does it need a co-star?
• Which GIF sums up your mood when my name pops up?
• Basic “hey” text or bold voice note—what do you prefer receiving?
• If I sent a late-night craving emoji, what snack would you deliver?
• What’s your secret to catching someone’s attention in three words?
• Describe today in one meme.
• Which streaming series would you binge with me and why?
• If your battery were at 5 %, whose text would you answer first?
• Sunrise selfie or midnight skyline pic—what should I send you?
• What’s your plan if autocorrect sells you out in a flirty text?
• Share the last song you added to your playlist—does it match our vibe?
• Typing indicators on or off: where do you stand?
• Which app reveals more about you—camera roll or notes?
• If you could DM any celebrity and guarantee a reply, who and what would you ask?
• Should our first inside joke be an emoji code? Which one starts it?

First-Date Flirty Questions

• If first dates had theme songs, what would ours be?
• Which moment of tonight will you replay before falling asleep?
• What part of your day did you save to tell me first?
• Do you judge a date by the appetizer or the goodbye?
• What’s one risk you’re glad you took that brought you here?
• Which seat—across from me or beside me—feels more exciting?
• If the check got lost, do we dine-and-dash or wash dishes together?
• What’s your secret test to decide if a second date is worth it?
• How often do you glance at the door vs. my eyes tonight?
• Which question are you hoping I’ll ask before dessert?
• If you could rate first-date jitters on a scale, where are you right now?
• What detail of mine did you notice first?
• Which part of the menu best describes your personality?
• If this night were a movie genre, what would it be?
• How would you tease me into scheduling the next adventure?

Adventurous Flirty Questions

• Which country would you whisk me to if we both called in “sick” tomorrow?
• What adrenaline sport secretly tempts you—and would you let me film it?
• Road trip playlist or silent staring at landscapes—which sounds sexier to you?
• Are you the “maps” guru or the “let’s get lost” type on a spontaneous drive?
• Which city’s food scene should witness our first brunch together?
• If we booked a mystery flight, what three items would you pack first?
• Would you skydive with me if I promised the view would be worth the scream?
• What’s one fear you’d crush just to impress me?
• Which weather makes you feel most alive—and most ready to kiss in the rain?
• Choose our joint bucket-list goal: northern lights or Bali sunrise?
• Which concert would you drop everything for if I scored front-row tickets?
• What’s the wildest place you’d dare to slow-dance under the stars?
• If I challenged you to a sunrise hike, what snack bribe would guarantee a “yes”?
• Sailboat or motorcycle—how would you rather escape for the weekend?
• Which adventure movie couple do we outdo with our chemistry?

How to Read His Answers (and Keep the Spark Going)

1. Listen for Tone, Not Just Words
   If he answers quickly with playful detail, excitement is high. Short, guarded replies may need gentler follow-ups.
2. Match Vulnerability Levels
   When he shares something personal, reciprocate. Balanced disclosure builds trust faster than one-sided probing.
3. Spot Opportunity Hooks
   If he mentions a shared interest—say, “I’d binge a sci-fi series”—suggest a watch party. Turning answers into plans keeps momentum rolling.
4. Mind the “Maybe Later” Topics
   Hesitation on a question about deep fears? Switch to lighter prompts and circle back when comfort grows.
5. Use Micro-Callbacks
   Reference an earlier answer (“still craving that beach sunrise?”) to show you’re listening and keep flirtation threaded through future chats.

Final Note

Flirty questions unlock stories, spark laughter, and lay the groundwork for meaningful connection. Use these prompts as conversation starting points, then let genuine curiosity guide the twists and turns. With the right blend of teasing and sincerity, you’ll move from light banter to shared adventures—one playful question at a time.