From Cleopatra’s legendary allure to Marilyn’s irresistible charm and Zendaya’s modern girl-next-door appeal, these icons have mastered the art of flirting with style and ease.
These fun and flirty questions to ask a guy are your secret weapons to bring him to his knees (or one knee) a la Tashi Donaldson.
Flirty Questions to Ask a Guy
Do you have any go-to flirting techniques or moves?When was the last time you felt butterflies?What delicious dinner would you prepare for me?Do you believe in love at first sight, or should I walk by again?What’s your idea of a perfect romantic getaway?How do you like to relax after a long day, and can I help?What is your most irresistible quality?How do you usually show someone you care?If I could prepare you breakfast in bed, what would you like to have?Have you ever fantasized about me?
Pay attention to how he responds to these questions. This is more valuable than the actual questions themself.
Gauge his response and you’ll be able to tell if he likes you.
As Robert Greene says in The Art of Seduction, “Seduction is a game of psychology, not beauty.”[1]
While I find half of Greene’s teachings outdated, I do agree with this: Seduction isn’t tied to looks or innate talent. It’s about your personal magnetism.
Look at those questions again. Which ones feel natural to you, and which could you never ask?
The key to flirting is being comfortable and genuine. Know your comfort zone and stick to it. If you’re not naturally playful, don’t force it — it’ll come off as fake and won’t last.
Rely on what feels right for you, don’t force anything, and let your natural charm shine through.
Flirty Questions to Ask a Guy to Make Him Laugh
In the very likely event of a zombie apocalypse, what’s your survival plan?Would you rather be a little bit thirsty until the end of your life or have to high-five everyone you meet?What’s the dumbest thing you believed about girls growing up?Which Disney princess is the sexiest?Sneakers with ankle socks or sandals with crew socks?How many memes per day do you think is the right amount to share with someone, and why is it 100?What’s the cringiest compliment you’ve ever given to someone, and what was their reaction?What's your most frequent shower thought?Who's your daddy: Indiana Jones, MacGyver, or Chuck Norris? Justify your answer.If I were a damsel in distress, how would you reach the tower to earn your kiss of true love without slaying the dragon?
Jeffrey Hall’s study in the journal Evolutionary Psychology found that men use humor to gauge women’s interest — if she laughs, she’s likely interested. However, an even better indicator of romantic connection is if the two are spotted laughing together.[2]
Hall says that shared laughter is a “pathway toward developing a more long-lasting relationship.”
These fun questions can show if his weird matches your weird. Whether you’re trying to charm a new guy or (re)ignite the spark in a long-term relationship, these lighthearted questions won’t leave him indifferent.
It’s simple: If he laughs, he’s your guy; if he suggests you need help . . . next!
Flirty Questions to Ask a Guy Over Text
How does this look on me? (Include a photo of yourself in a flattering dress.)Are you interested in anyone right now? Asking for a friend.What was your first impression of me when we met?What’s something nonphysical that you find attractive?Has anyone ever told you how nice your eyebrows are?You were in my dreams last night. Want to hear about it?Do you consider yourself a good kisser?Is it okay that I kind of want to kiss you right now?Why is it that I love talking to you this much? Any theories?When am I seeing you next?
That blush on your face when you get a flirty message from your crush. Absolutely priceless.
The bad thing about texting is that you’re not face-to-face.
The good thing about texting is that you’re not face-to-face, so you can ask him questions a tad more provocative than you would in person.
For example: “Is it okay that I kind of want to kiss you right now?” in person might come across as overly forward, but in a text it’s juicy and ignites a spark of anticipation.
I’m not suggesting you discuss serious things over text — too much can get lost in translation.
But if you’re shier than most and feel more comfortable asking certain things via text, this is your medium. That’s what texting was invented for! (Ok, it wasn’t, but it’s what we all used it for when it first came out.)
Flirty Icebreaker Questions
What’s your favorite color?
Just kidding, hardly anyone cares about that. But it’s magenta since you’ve already asked.
What were you most excited to buy this year?Do you have a “bucket list,” and have you completed anything from it?If you had to delete all but three apps, which ones would you keep?What would be your dream job if money didn’t matter?If you could live anywhere in the world, where would you live and why?What’s one thing that never fails to make you cringe?If you had an unexpected day off tomorrow, what would you do?If you hosted a podcast, what would it be about?What is your favorite season?What is something you love doing but feel guilty about?
I love messing with people on dating apps by asking the most mundane, open-ended questions I can think of to test their patience and dedication. It’s all for research, I swear!
But don’t be like me.
These random, open-ended starters are perfect for actually getting to know someone. Asking the right questions eases the initial awkwardness and helps you see if he’s even worth your time. I mean, if his favorite podcast is Tate Speech, why bother?
Throw in some thought-provoking, daring, and flirty questions to spice things up. It’s a fun way to connect, and who knows? You might even find someone worth deleting those godforsaken apps for!
Low-Key Flirty Questions to Ask a Guy
Do you like weather?Do you like music or are you a cyborg?What color is your toothbrush?If pets are the new children and plants are the new pets, how many plants do you want to have?Can you touch your nose to your tongue?Pineapple on pizza: yes or no?Do you believe in life after love?Do you like getting jiggy with it?Why so serious?Do you ever feel like a plastic bag, lifting through the wind, wanting to start again?
I guess my point is that overthinking can make you sound stiff and awkward, like Mr. Collins trying to impress the Bennet family or Jonah Hill’s character fumbling through awkward conversation with Ice Cube in 22 Jump Street.
It’s totally normal to feel tongue-tied around your crush and say things you might regret. But take a deep breath and repeat after me: “I got this.”
Flirting is a state of mind, and you can only tap into it when you’re relaxed and at ease.
Whatever questions you ask — aside from those cringe-worthy ones I just mentioned — will be fine.
It’s all about genuinely wanting to get to know someone, not showing up to a date with a pre-written script.
Think about what you actually want to ask the guy to get to know him better and go with that. And if you need some inspiration, with this article we’ve got you covered.
Remember, you’ve got this!
Flirty Truth Questions to Ask a Guy
What's your biggest insecurity?What’s your secret guilty pleasure?What's your worst habit?When was the last time you lied?When was the last time you cried?Who was the last person you kissed?What’s your biggest turn-off?What’s the weirdest thing that turns you on?Have you ever cheated on a partner?Why did your last relationship break down?
When you’ve met a guy and you’re looking to move beyond subtle flirty questions, truth questions are a great way to delve into the depths of his world.
Turning it into a truth or dare game can keep it fun and prevent things from getting too intense.
Mix in deep questions and intimate ones. This approach not only makes things more exciting but also helps you deepen your connection whether you are getting to know someone new or trying to keep the spark alive as a married couple.
Maintaining eye contact while asking can make the conversation more engaging and a bit uncomfortable in an exciting way. So, truth or dare?
Conclusion
Use these cheeky questions as conversation starters whether you’re breaking the ice with a new crush or trying to revive the spark.
Remember, subtle can be just as sexy as bold, but don’t be afraid of deeper questions.
These flirty questions will help you navigate romance Cleopatra-style, creating a fun, engaging, and romantic vibe that leaves a lasting impression.
So, go ahead and get flirty!
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FAQs
How do you ask a guy intimate questions?
To ask a guy intimate questions, focus on making him feel comfortable. Keep the tone casual and ensure the setting is relaxed to encourage openness and trust. Don’t hesitate to go with flirty questions, but keep the conversation respectful.
How do I know if I’m coming across as too aggressive?
You know you’re coming across as too aggressive if he shuts down after seeming interested at first. Aggressive flirtation can hinder a natural exchange. Observe how the person accepts your approach and tailor your questions accordingly. With someone you’ve just met, avoid daring questions initially and let the interaction unfold comfortably.
How do you know when you have a crush on someone?
You know you have a crush on someone when you think about them all the time and your heart races in their presence. Wanting to be near him and attempts at flirting are some early signs that you are into him. These actions naturally show your interest and excitement.
References
1. Greene, R. (2001). The art of seduction. Viking.
2. Hall, J. A. (2015). Sexual selection and humor in courtship: A case for warmth and extroversion. Evolutionary Psychology, 13(3).
https://doi.org/10.1177/1474704915598918