Texting someone you’re into can be fun, but let’s be real—it can also be a little meh if the convo flatlines after a few “wyd” messages.
Been there. Scrolled past that.
If you’re trying to flirt and get to know him better, asking the right questions is your secret weapon. Not deep interrogation-level stuff. Just light, cheeky questions that make him open up, lean in, and maybe blush a little.
This list gives you 60 flirty questions that keep the vibe fun while letting you peek behind his cool-guy curtain. Whether you’re just getting started or already trading “good morning” texts, these questions will spark conversations worth staying up for.
Cute and Curious Icebreakers
Perfect when you’re starting to flirt but still testing the waters
- “What’s something random that always makes you smile?”
- “What was your first-ever crush like?”
- “What kind of texts secretly make you blush?”
- “Do you believe in love at first sight or slow burn?”
- “What’s your biggest weakness when it comes to someone you like?”
- “If I dared you to send a flirty selfie right now… would you?”
- “What’s one compliment you always remember?”
- “What kind of flirting actually works on you?”
- “What do you usually notice first about someone?”
- “Would you rather cuddle all day or kiss all night?”
Playful Teasing Questions
To add some spark without going full drama
- “Be honest—how good are your kissing skills on a scale from 1 to ‘trust me’?”
- “What’s something you think you’re good at… but might not actually be?”
- “If I showed up at your place right now, what would I catch you doing?”
- “Do you think I’d be a good or terrible influence on you?”
- “Have you ever flirted your way out of trouble?”
- “Who flirts better—you or me?”
- “What’s your ‘secret weapon’ when you’re trying to impress someone?”
- “How long could you go without texting me?”
- “If I dared you to tell me one juicy secret, could you handle it?”
- “How often do you check your phone hoping it’s me?”
Questions That Get a Little Deeper
Flirty and thoughtful—because cute convos deserve substance too
- “What kind of person completely draws you in?”
- “When do you feel the most confident?”
- “Have you ever had a connection that surprised you?”
- “What’s something romantic you’ve actually done—not just thought about?”
- “What makes you feel close to someone?”
- “Do you think you’re more of a heart-first or head-first kind of guy?”
- “What’s your love language—and what’s your flirting language?”
- “Have you ever told someone how you really feel and instantly regretted it?”
- “What’s something most people don’t know about how you flirt?”
- “Do you believe in soulmates, or do you think it’s about timing?”
Sneaky Bold Questions
Let the spice creep in—without making it awkward
- “What’s something totally innocent that still turns you on?”
- “If I was sitting next to you right now… what would you be thinking?”
- “What would you do if I whispered something in your ear right now?”
- “What’s your go-to move when you really like someone?”
- “What’s something you wish I’d ask you right now?”
- “Do you think you’d survive a staring contest with me in person?”
- “If I gave you a five-second window to kiss me… would you take it?”
- “What’s the most daring thing you’ve ever done for someone you liked?”
- “If I challenged you to charm me in 10 words, could you do it?”
- “Do you talk to other girls like this—or am I special?”
Sweet and Slightly Sappy (But Still Flirty)
The kind of questions that make him smile and think a little
- “What kind of compliments do you secretly love hearing?”
- “What’s something about yourself you’re secretly proud of?”
- “When did someone last surprise you in a good way?”
- “What do you wish more people noticed about you?”
- “What’s your softest side—and who gets to see it?”
- “If I asked you what makes me stand out, what would you say?”
- “What’s something romantic you’ve always wanted to try?”
- “Have you ever had a moment with someone that felt like a movie scene?”
- “What makes you feel really wanted?”
- “What do you notice when you really like someone?”
Fun Hypotheticals That Still Flirt
Because imagination is sexy too
- “If we were stuck on an island together, who would flirt first?”
- “If you had 24 hours with me—no rules, no distractions—what would we do?”
- “Would you rather kiss me under the stars or during a rainstorm?”
- “If I could teleport to your place right now, what’s the first thing you’d say?”
- “If we had a secret date night, where would we go?”
- “Truth: Have you imagined kissing me yet?”
- “Would I win you over more with a flirty text or a teasing voice note?”
- “What song would you put on if we were dancing alone together?”
- “If I challenged you to make me blush, what’s your first move?”
- “If this convo ended with us making plans… would you be into that?”
Why Flirty Questions Work So Well
Flirty questions don’t just keep the convo going—they make him want to keep texting.
They’re light enough to feel fun, but personal enough to build connection. When you ask questions that play with both curiosity and attraction, he opens up naturally—and probably flirts right back.
It’s not about saying the perfect thing. It’s about giving the moment some spark.
When to Send These
There’s no rulebook, but here are a few golden moments:
- Right before bed (so the convo lingers in his head)
- During a random break in the day (bonus points for surprise factor)
- After a fun date or voice call
- When the convo slows down but you don’t want it to end
Just match his vibe, keep it playful, and let the questions do the rest.
Final Thought
Flirty questions are like your texting superpower. They shift the energy, build attraction, and make boring small talk a thing of the past.
You don’t have to overthink it.
Pick one. Hit send. Smile at his reply.
He’ll open up. He’ll flirt back. And he’ll probably think, “Damn, she’s good at this.”