50 Flirty Questions to Ask a Guy You Like

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Flirting is such a fun way to spark connection, isn’t it? Whether you’re getting to know someone new or trying to keep the fire alive with someone you already adore, flirty conversations can make everything feel lighter and more exciting. I love how the right questions can tease, intrigue, and create those moments where you can’t help but smile; and maybe even blush a little.

This post is packed with flirty questions that are perfect for spicing up any conversation. Whether you’re texting late at night or hanging out in person, these questions add just the right mix of charm and playfulness. And the best part? They’re not awkward or forced; they flow naturally, making it easy to keep things fun and relaxed.

Each section brings a different vibe, so you can pick and choose what works best for the moment. Want to keep it sweet and romantic? There’s a section for that. Feeling bold and cheeky? You’ll find plenty of ideas to make him laugh or get him thinking about the two of you.

Flirty questions are such a simple way to create chemistry and show a little interest without going overboard.

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Fun and Cheeky Questions

A little playful banter can go a long way when you’re getting to know someone. These fun and cheeky questions add just the right amount of sass to keep him intrigued. You’ll have him laughing, blushing, and maybe even trying to out-flirt you.

1. If I dared you to make me laugh, what’s the first thing you’d say?
2. What’s one thing about me you think I don’t realize is totally irresistible?
3. If we were stranded on a deserted island, how long would it take before you started flirting with me?
4. What’s the most ridiculous pickup line you’d actually try on me?
5. If you had to describe me in one word, what would it be—and why?
6. Would you rather cuddle up with me during a storm or take me out dancing in the rain?
7. If we swapped phones for a day, what’s the first thing you’d text yourself from mine?
8. What’s one thing you’d want to teach me if we spent the whole day together?
9. If you could steal one thing from me, what would it be—besides my attention?
10. What do you think would happen if we were locked in a room together for 24 hours?

Romantic and Sweet Questions

Sometimes, flirting is all about setting a romantic mood. These sweet and flirty questions are perfect for turning up the charm while still keeping things light. It’s like adding a touch of romance to a playful conversation.

1. What’s one thing you’d plan for us if I gave you the perfect date challenge?
2. If we were slow dancing right now, what song would you want playing in the background?
3. What’s your favorite thing about the way I smile at you?
4. If I told you I’d cook dinner for you, what’s the one dish you’d hope I’d make?
5. What’s the most romantic thing you’d want us to do under the stars?
6. How would you describe the way I make you feel in three words?
7. If I told you I had a crush on you, how would you respond?
8. What’s one thing you’d never get tired of doing with me?
9. If we had our own secret hideaway, what would you want to keep there just for us?
10. What’s your idea of the perfect kiss—asking for research purposes, of course?

Playful “What If” Scenarios

Flirting gets even better when you throw in some creative “what if” questions. They’re a fun way to imagine scenarios that make him laugh, blush, and think about the two of you together.

1. What if I told you I could beat you at your favorite game, would you let me win or challenge me?
2. What if I accidentally fell asleep on your shoulder, would you move or just let it happen?
3. What if we had to act like a couple for a day, how convincing do you think we’d be?
4. What if you had to pick my outfit for a date, what would you choose?
5. What if I told you I had a surprise planned for us, how curious would you be?
6. What if I said I wanted to plan a spontaneous adventure, where would you want us to go?
7. What if we were playing Truth or Dare, would you choose truth, dare, or me?
8. What if I challenged you to a staring contest, who do you think would win?
9. What if we were caught in a power outage, what would you do to keep us entertained?
10. What if I asked you to teach me something, what would you choose and why?

Slightly Bold and Flirty

Sometimes, being a little bold can really amp up the excitement. These flirty questions walk that fine line between playful and daring, keeping the conversation thrilling and fun.

1. What’s the first thing you noticed about me that caught your eye?
2. How do you feel about taking the lead, on the dance floor or anywhere else?
3. If I told you I’m bad at being subtle, would you ask me what I’m really thinking?
4. What’s one thing you think you’d love doing with me that we haven’t done yet?
5. If I asked you to describe your idea of the perfect kiss, what would you say?
6. If I dared you to make the first move, what would it be?
7. How would you feel if I said you were my favorite part of today?
8. What’s one thing about me that makes you want to get to know me even more?
9. If I told you I’m terrible at keeping secrets, what’s the one thing you’d want me to spill?
10. How do you feel about letting me win at something—or do you love a good challenge?

Lighthearted and Fun Questions

Flirting doesn’t always have to be serious. Sometimes, keeping it lighthearted and goofy is the best way to make someone feel at ease and keep the energy fun and relaxed.

1. What’s your go-to guilty pleasure snack, and would you share it with me?
2. If I asked you to sing your favorite song, how confident would you be?
3. If we were playing charades, how competitive do you think I’d get?
4. If I dared you to pick the cheesiest romantic movie for us to watch, what would you choose?
5. If I stole your phone, what’s the first thing you’d worry I’d find?
6. If I told you I had a terrible joke to tell, would you want to hear it anyway?
7. What’s one silly thing you’d love to do with me that you’d never do alone?
8. If we were at an amusement park, which ride would you convince me to go on?
9. What’s one random fact about yourself that you think would impress me?
10. If I told you I’m terrible at picking movies, would you step up and choose for us?