250 Flirty Questions to Ask a Guy

Want to start fun talks with a guy you like? Not sure what to say?

Don’t worry – we’ve got your back! Here’s a list of 250 questions to help you get to know him better.

These aren’t boring old questions – they’re friendly, fun ways to start good talks and learn what he likes, thinks about, and hopes for.

You can use these whether you just met someone new or want to make your boyfriend or husband smile.

Some questions are light and fun. Others help you learn more about his heart and mind.

No need to feel shy or stuck – pick a question and let the talk flow naturally!

Flirty Questions for a Guy You Like

What’s something you’re passionate about that most people don’t know?
What’s the most daring thing you’ve ever done?
What’s a quality you really admire in someone?
If you could pick any place for a first date, where would it be?
What would you do if you had a whole day to yourself and no plans at all?
What’s the most romantic thing you’ve ever done for someone?
Do you believe in fate, or do you think we create our own destiny?
How do you like to spend your weekends when you’re not working?
What’s your idea of the perfect date night?
What’s the most spontaneous thing you’ve ever done?
What’s the first thing you notice about someone when you meet them?
If I gave you a challenge to make me smile right now, what would you do?
What’s one thing you’d love to try if you weren’t afraid to fail?
How do you feel about surprises, good or bad?
Do you prefer texting or talking in person when you’re getting to know someone?
What’s your guilty pleasure that no one else knows about?
What’s one thing you’ve never told anyone but would be willing to share with me?
What’s the most attractive quality in a woman to you?
If we went on a spontaneous road trip, where would you take me?
What’s the best compliment you’ve ever received from a woman?
How would you feel if I complimented you right now out of the blue?
If you could do anything for a day with no limits, what would it be?
How do you feel about public displays of affection?
Would you ever want to take a trip with someone you just started dating?
What’s something you look for in someone when you’re starting to get to know them?
How would you describe your ideal girl?
Do you like it when someone texts you out of the blue, or is that a bit too forward?
What’s your idea of the perfect lazy day?
If I invited you on a spontaneous weekend getaway, would you be up for it?
What’s your favorite way to show someone you care?
What would you do if you caught me looking at you from across the room?
How would you feel if I kissed you first?
What’s the first thing that comes to your mind when you think of a perfect relationship?
What’s your favorite way to be spoiled?
If you could describe your perfect woman in three words, what would they be?
What’s the most flirtatious thing you’ve ever done?
What’s something you find irresistible in a woman?
What’s your favorite type of date—casual and fun or formal and romantic?
How would you feel if I made the first move and kissed you?
Do you believe in love at first sight, or do you think it takes time?
What do you think about love and relationships in general?
If we were to go out right now, what would be your idea of a fun night?
What’s your biggest turn-on?
How would you feel if I invited you to a fancy dinner just for fun?
What’s something you’ve always wanted to do with a partner?
If I surprised you with tickets to an event, would you be thrilled or overwhelmed?
How do you feel about being in the spotlight during a date?
What’s your most romantic memory?
If you were to take me on a date, how would you make it special?
What would be your reaction if I showed up at your door with a surprise?

Flirty Questions to Impress a Guy

What’s the most charming thing a girl can do to get your attention?
If I asked you to dance right now, would you do it?
What’s one thing you find irresistible about me already?
Do you believe in love at first sight, or should I walk by again?
What’s the most romantic thing you’d do to impress a girl?
If I whispered something sweet in your ear, would you melt?
What’s one thing you would do to make a date unforgettable?
What’s your idea of a perfect flirty exchange?
How do you feel about spontaneous kissing?
What’s one thing you’d do to sweep me off my feet?
How would you feel if I gave you a compliment right now?
Would you rather go on a spontaneous adventure or a perfectly planned date?
Do you like it when a girl plays hard to get?
What’s your idea of a cute, flirty text message?
How would you react if I kissed you out of nowhere?
Would you like it if I surprised you with a cute date idea?
What’s one thing a girl could do to make you feel special without words?
What’s the best way to get you to smile on a bad day?
How would you feel if I told you I was thinking about you right now?
If I gave you a secret, would you keep it safe?
What’s the best kind of flirtation for you?
How would you react if I showed up at your door with a romantic dinner?
Would you be down for a spontaneous date night with no plans?
What would you do if I texted you something flirty and unexpected?
How would you feel if I gave you a slow, lingering kiss?
Would you ever serenade me with a song if I asked?
What’s something I could do to impress you on a date?
How do you feel about making the first move—would you do it?
What’s the most flirtatious thing you’ve ever said to someone?
How would you feel if I surprised you with something playful and unexpected?
Do you like a girl to be bold or more subtle in her approach?
What’s the most spontaneous date idea you’ve ever had?
How would you feel if I kissed you without warning?
What’s the sweetest thing you’ve ever done to impress someone?
If I called you up for no reason, would you be curious to know why?
What would you think if I told you I was interested in you after just meeting?
How do you feel about texting late at night just to chat?
What’s the most daring thing you’ve ever done on a date?
How would you feel if I gave you a playful compliment right now?
What’s something you like to do to show someone you’re thinking of them?
How would you feel if I invited you to a private, intimate dinner at home?
What would be your reaction if I made a bold move on our first date?
Would you like me to plan our next date, or would you prefer to take charge?
How do you feel about getting attention from someone you’re interested in?
What’s your favorite way to be surprised by a girl?
Would you like it if I made you laugh with a funny, flirty joke?
How do you feel about holding hands in public?
What’s one thing that would really impress you on a date?
How would you feel if I gave you a surprise kiss at the end of the night?
What’s your favorite way to have fun on a spontaneous date?

Flirty Questions for Your Partner or Husband

What’s your favorite way to flirt with me?
How would you feel if I gave you a surprise kiss right now?
What’s one thing you love about our relationship that makes you smile?
If you could take me on a romantic getaway, where would we go?
Do you ever get butterflies when you see me after a long day?
What’s the most romantic thing I’ve ever done for you?
How would you react if I sent you a flirty message during the day?
Do you think it’s cute when I flirt with you in front of others?
What’s one thing I could do to make you feel extra special today?
How would you feel if I gave you a playful surprise for no reason?
What’s your favorite memory of us together?
Would you want me to plan a special date just for the two of us?
How would you react if I gave you a spontaneous hug or kiss?
What’s the best compliment I’ve ever given you?
What’s one thing I could do to make our next date night unforgettable?
How would you feel if I told you I was thinking about you all day?
What’s the most playful thing you’d like me to do for you?
Do you think it’s sexy when I tease you?
What would you do if I told you I missed you while we were apart?
Would you be up for a spontaneous kiss right now?
What’s your favorite way for me to show affection towards you?
How would you feel if I whispered something sweet to you in public?
Do you like it when I surprise you with little romantic gestures?
What’s one thing you’ve always wanted to do with me but haven’t yet?
How do you feel when I compliment you unexpectedly?
What would you do if I planned a surprise date night just for us?
How would you feel if I bought you something special, just because?
What’s the most flirtatious thing I’ve ever done to you?
What’s one thing I could do to make you fall in love with me all over again?
How would you feel if I gave you a passionate kiss after a long day?
What’s one thing I do that always makes you smile?
How would you feel if I showed up at your work with lunch and a kiss?
What’s your favorite way for me to make you feel appreciated?
What’s something you’ve always wanted to try in our relationship that we haven’t done yet?
How would you feel if I sent you a text saying how much I missed you?
What’s the most spontaneous thing you want us to do together?
Would you want me to leave a sweet note for you to find unexpectedly?
How would you feel if I kissed you in a public place just because I wanted to?
What’s something playful I could do to make you laugh today?
How would you feel if I made the first move in a flirtatious way?
What’s your favorite thing for me to do when we’re alone together?
Would you want me to surprise you with a spontaneous romantic gesture?
How do you feel about spending a whole day together, just enjoying each other’s company?
Would you like me to send you a flirty text while we’re apart to make you smile?
What’s your idea of the most romantic evening we could spend together?
How would you feel if I planned a surprise weekend getaway for the two of us?
What’s the most affectionate thing I could do for you right now?
How would you feel if I sent you a sexy message during the day to keep things exciting?
What would you do if I gave you a spontaneous kiss just because I was thinking of you?
How do you feel when I give you a random compliment or surprise?

Flirty Questions to Keep the Conversation Going

What’s the craziest thing you’ve ever done on impulse?
How would you feel if I asked you to dance right here, right now?
If I asked you for a kiss, how would you react?
How do you like to be surprised?
What’s the best way to keep you entertained during a long conversation?
Would you ever let me surprise you with a spontaneous adventure?
What’s one thing that always makes you smile?
If you could steal a kiss right now, how would you do it?
What’s your idea of a fun, flirty challenge?
How do you feel about spontaneous dates with no plans?
Would you let me plan an exciting evening for us?
What’s something playful you’d love to try together?
How would you feel if I teased you in a playful way?
What’s your favorite way to flirt with someone?
If I gave you a random compliment, would you blush?
How would you feel if I kissed you in front of all your friends?
What’s one thing you find incredibly charming in someone?
If I could take you anywhere right now, where would it be?
Would you let me pick a fun, unexpected activity for our date?
How do you feel about spontaneous road trips?
What’s the most playful thing you’d like to try together?
How do you feel about flirty text messages throughout the day?
What’s your idea of a perfect night in with someone special?
Would you rather go on a flirty, casual date or something more romantic?
What’s the most daring thing you’d do to impress me?
How would you feel if I whispered something playful in your ear?
What’s the most exciting way you like to spend your time with someone?
Would you be down for a spontaneous night of fun?
What’s something romantic you’ve always wanted to try?
How would you feel if I gave you a playful, teasing compliment?
What’s one thing you’d like to do to impress someone on a date?
How do you feel about receiving unexpected, sweet texts?
What’s one question you’d ask to make someone blush?
Would you prefer a spontaneous kiss or a planned, romantic one?
How would you feel if I whispered something secretive in your ear?
Would you want me to plan a surprise, spontaneous date for us?
What’s one way I could really surprise you on a date?
How would you feel if I asked you to meet me for a spontaneous adventure?
What would you do if I gave you a playful kiss out of nowhere?
How do you feel about surprise getaways for the weekend?
What’s one thing I could do to make you laugh today?
How do you feel about long, flirtatious texts?
What would you do if I gave you a playful compliment right now?
How would you react if I invited you for an impromptu dinner?
Would you like it if I sent you a cute message just to make you smile?
How would you feel if I showed up with a surprise gift just because I was thinking of you?
Would you let me make the first move next time we hang out?
How do you feel about spontaneous moments of affection?
What’s one thing you’d like to try on a playful date?
What’s your idea of a perfect flirty conversation?

Flirty Questions for a Shy Guy

What’s the best way to get you to smile when you’re feeling shy?
What’s something you find really cute that most people don’t notice?
How would you feel if I gave you a compliment out of nowhere?
What’s one thing you’ve always wanted to say but never have?
Would you like it if I asked you to go somewhere quiet and just talk?
What’s one thing you find irresistible in someone you like?
How do you feel about holding hands in public?
What’s your idea of a fun, relaxed date?
Would you be comfortable if I gave you a soft, lingering kiss?
What’s one way I could make you feel more at ease around me?
How do you feel about sweet, simple compliments?
What’s something you secretly like doing but haven’t shared with many people?
Would you like it if I made you laugh with a funny joke?
How do you feel about quiet moments spent just being with someone special?
What’s something playful that always makes you feel happy?
Would you prefer a calm, intimate date or an exciting one with a lot of activities?
How do you feel when someone gives you a sincere compliment?
Would you like it if I gave you a quick kiss to make your day?
What’s one thing girls do that is really cute?
How would you feel if I texted you something sweet right now?
Would you be open to getting to know me more through small moments together?
How do you feel about giving and receiving small surprises?
What’s something I could do to make you feel more comfortable opening up?
How do you feel when someone shows interest in you?
Would you like it if I made you feel special by doing something simple yet thoughtful?
How would you react if I gave you a soft, sweet hug out of the blue?
What’s something that instantly makes you feel good about yourself?
How would you feel if I initiated a playful conversation to lighten things up?
Would you like it if I surprised you with something small and thoughtful?
How do you feel about receiving little affectionate gestures?
Would you prefer a quiet evening spent talking over dinner or a fun night out?
How do you feel when I compliment you on something you may not have noticed about yourself?
What’s the most romantic thing someone has ever done for you?
Would you like it if I told you how much I admire your shyness?
How do you feel when someone gives you space to be yourself?
Would you like me to text you just to make your day better?
How do you feel about sharing your feelings with someone you trust?
Would you like it if I whispered something sweet to you?
How would you feel if I asked you to spend a day with me, doing whatever feels right?
Would you like me to hold your hand in a crowd?
How do you feel when someone notices something special about you?
What’s something you love about yourself that you don’t often share with others?
How do you feel when someone is kind and thoughtful toward you?
Would you like me to send you a simple, sweet message just to let you know I’m thinking of you?
How would you feel if I kissed you on the cheek as a gentle surprise?
What’s one thing that makes you feel really confident?
Would you be open to spending more time together, just enjoying each other’s company?
How do you feel about sharing your dreams with someone you trust?
What’s one thing you’d love to do with me, even if it’s a little out of your comfort zone?
How would you feel if I made you laugh with a playful, flirty comment?