Sparking a fun, lighthearted connection often starts with the right question. Whether you’re looking to break the ice on a first date, tease out someone’s playful side, or add a fresh twist to your existing relationship, a little flirtation can go a long way.
Below, you’ll find a variety of flirty questions you can ask a guy in different scenarios—ranging from casual laughter to deeper conversations—to help you both smile, bond, and maybe even feel a few butterflies along the way.
Things to Know Before You Ask:
- Be Yourself
Authenticity is attractive. Pick questions that reflect your personality and keep the conversation comfortable. - Know Your Comfort Zone
Respect each other’s boundaries. If a question feels too personal, save it for later. - Aim for Balance
Good conversations flow both ways. Share your own thoughts and answer similar questions to build mutual trust. - Use the Right Tone
Adjust your approach based on how well you know him and the setting. What’s fun on a casual date might be too bold for a first meeting. - Have Fun
Flirting should be lighthearted. Don’t overthink it—enjoy the process of getting to know each other.
Flirty Icebreaker Questions
What’s your go-to move when you’re trying to impress someone?
If you could pick one song to describe your vibe, what would it be?
Which fictional character best matches your personality?
What’s your most spontaneous guilty pleasure?
Would you rather be the world’s best kisser or the world’s best dancer?
What’s the most adventurous thing you’ve done this year?
If confidence were a superpower, how would you use it?
What’s your favorite “getting to know you” question to ask someone new?
On a scale from 1 to 10, how big is your sweet tooth?
Do you believe in love at first sight, or do you need a second glance?
If you could learn a skill instantly, what would it be?
Beach day or city skyline at night—which suits your mood better?
If you were to start a band, what would you name it?
What’s something random that always makes you smile?
Do you prefer playing it safe or taking chances in life?
If you could bottle one scent forever, what would it smell like?
What’s the strangest compliment you’ve ever received?
Do you have any hidden talents people would be surprised by?
What’s your idea of the perfect first date?
If you had to choose one word to describe yourself, what would it be?
Flirty Questions to Ask a Guy to Make Him Laugh
If you were a dessert, what would you be and why?
What’s the funniest thing you’ve done just to impress someone?
If your life had a theme song, which cartoon would sing it?
Have you ever pretended to like a terrible movie just to sound cool?
If you could swap lives with a celebrity for a day, who would it be?
What’s your most embarrassing childhood nickname?
If a genie granted you one ridiculous wish, what would you ask for?
Which dance move can you totally nail—or at least think you can?
Do you have a secret karaoke anthem you rock out to?
What’s the weirdest joke you still find hilarious?
If you hosted your own reality TV show, what would the premise be?
What’s your favorite cheesy pickup line (that actually works sometimes)?
If you were a pizza topping, which one would capture your essence?
Would you rather have the hiccups nonstop or laugh uncontrollably at serious moments?
What’s your go-to goofy face when taking selfies?
Have you ever practiced a wink in the mirror just to get it right?
Which movie scene cracks you up no matter how many times you watch it?
If you were a meme, what caption would go with your photo?
Do you have any offbeat fears that make people laugh when you explain them?
What’s the lamest excuse you’ve ever made to skip something?
Fun Flirty Questions to Ask a Guy
If you could plan the ultimate day off, what would it look like?
Which fictional world would you love to live in for a week?
Do you have a go-to trick for turning a boring day into a fun one?
What’s the coolest thing on your bucket list right now?
Ever had a moment that felt like it came straight out of a romantic comedy?
If you could master any board game instantly, what would it be?
When you think of “fun,” what’s the first image that pops into your head?
What’s the best compliment you’ve ever received from a stranger?
If you could have any exotic pet for a day, which one would you choose?
What’s your craziest wish if money or rules weren’t an issue?
Do you ever plan random road trips just for the thrill of it?
Do you have a signature drink that captures your personality?
If you could relive any day, which day would you choose?
What random talent would you love to learn for no particular reason?
Are you more of a prankster or the victim of pranks?
If you could design a theme park ride, what would it be like?
Have you ever tried an unusual hobby that surprised you?
What’s your favorite part of the day—morning, afternoon, or night?
Do you believe in dressing up for no reason, just to have fun?
What’s something quirky about you that most people don’t know?
Deep Flirty Questions to Ask a Guy
What do you think makes a real connection between two people?
What’s one thing you’ve learned about yourself from past relationships?
Do you believe people are drawn together by fate or by choice?
If you could change one thing about how people perceive you, what would it be?
What do you think is your most attractive quality beyond looks?
How do you handle vulnerability in a relationship?
Do you think soulmates exist, or is that just a romantic notion?
What’s a life lesson you wish you’d learned sooner?
Which personal goal are you most passionate about right now?
How do you recognize when someone truly cares about you?
What’s your favorite way to show someone they matter to you?
Do you have a personal mantra that keeps you grounded?
What’s one thing you wish more people understood about you?
If you could have one conversation with your younger self, what would you say?
What does emotional intimacy mean to you?
How important is it for you to maintain independence in a relationship?
Which experiences have shaped your views on love the most?
Do you believe in second chances, or do first impressions last forever?
How do you define “forever” when it comes to relationships?
What do you want most out of a deep, meaningful connection?
Flirty Truth Questions to Ask a Guy
Have you ever made a bold first move that you’re proud of?
What’s the most romantic thing you’ve ever done spontaneously?
Have you ever had a “love at first sight” moment?
What’s your biggest turn-on that surprises people?
Do you prefer to do the chasing, or do you like being pursued?
What’s a silly fear you’ve told no one about?
Do you ever get butterflies when you think about someone special?
Which personal habit do you think is irresistible?
Have you ever kept a secret crush for way too long?
What’s a fantasy date you’ve imagined but never tried?
What’s the boldest text you’ve ever sent to someone you like?
Have you ever written a love letter (or email) you were too scared to send?
Which compliment gets you every time?
If you were asked to share one guilty pleasure, what would it be?
Have you ever caught yourself daydreaming about someone at the worst possible time?
What’s your favorite way to feel close to someone, even if you’re far apart?
Have you ever regretted not shooting your shot with someone?
What do you do when you really want someone to notice you?
Do you have a memory that makes you blush whenever you recall it?
If your crush challenged you to a dare, how far would you go?
Low Key Flirty Questions to Ask a Guy
What’s one way you like to show someone you’re thinking of them?
Do you have a signature “smirk” that appears when you’re flirting?
What’s the simplest thing that instantly brightens your mood?
Have you ever sent someone a random meme just to start a conversation?
How do you usually let someone know you find them attractive?
What’s your favorite subtle way of flirting—eye contact, smiling, or playful teasing?
Is there a small act of kindness that always melts your heart?
Do you prefer a bold expression of interest, or something more understated?
Have you ever changed your outfit at the last minute because you thought you might see someone special?
What’s the tiniest detail you notice about someone you like?
Do you have a go-to compliment that never fails to win a smile?
How much do you rely on body language when flirting?
If you only had five words to flirt with someone, what would you say?
Do you think digital flirting can be as exciting as in-person flirting?
Has anyone ever won you over with just a simple phrase?
What’s something small and sweet that never fails to make you feel appreciated?
Do you prefer spontaneous compliments or planned gestures?
If you secretly had a crush on someone, how would you hint at it?
How do you balance being friendly and being flirty without crossing a line?
Do you think subtle gestures can be more powerful than grand declarations?
Flirty Questions to Ask a Guy Over Text
What’s the first thing you thought of when you woke up today?
If you could teleport me to your side right now, would you?
What’s your go-to emoji when you’re in a flirty mood?
Which song would you dedicate to me if you could?
If I were there with you, what would we be doing?
How would you describe your perfect evening in three words?
Have you ever texted someone all night until sunrise?
What’s the most random thought you had about me today?
On a scale of 1 to 10, how excited are you to see me next time?
Ever caught yourself smiling at your phone screen because of a text?
Would you rather send a funny GIF or a sweet text to cheer someone up?
If I popped into your dreams tonight, what do you think would happen?
What’s one thing you wish you could tell me in person right now?
If you could plan a spontaneous adventure, where would we go?
What’s the cutest text you’ve ever received from someone you liked?
When you can’t sleep, what’s the first thing that crosses your mind?
If you had to guess, what’s my favorite time of day to text you?
Ever found yourself reading old messages just to smile again?
What’s your secret to sending the perfect late-night text?
If you had to describe our vibe in one sentence, what would it be?
FAQs: Flirty Conversation Tips
- How do I know if he’s comfortable with these questions?
Pay attention to his reactions. If he seems distant or uncomfortable, shift to lighter topics or ask if he wants to talk about something else. - What if I’m nervous about being too forward?
Start with playful, low-key questions and gauge his response. If he engages happily, gradually move into deeper or more direct topics. - How can I keep the conversation going after asking a flirty question?
Share a bit about yourself in response to his answer. Show genuine interest by asking follow-up questions that let him expand on his thoughts. - Is it okay to ask these questions over text rather than in person?
Absolutely. Texting can sometimes make people more comfortable. Just be aware that tone can be misunderstood, so keep it clear and lighthearted. - Should I reciprocate by answering the same question?
Often, yes. It shows you’re genuinely interested in mutual sharing, and it keeps the flow balanced and fun.
Flirting is as much about listening and responding as it is about asking great questions. Whether you’re aiming for a playful laugh or deeper emotional connection, these prompts offer a gentle way to explore someone’s personality and spark meaningful exchanges. Enjoy the process, stay authentic, and let the conversation naturally unfold—who knows what exciting discoveries lie ahead.