94 of the Smartest, Most Insightful & Effective Questions to Ask a Girl

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There are few feelings more nerve-racking than scouring your brain to think of the right questions to ask a girl.

Your mind starts racing, your heart starts pumping, your palms start sweating, but in that particular moment, all you really want is to make your mouth start moving.

Pretty girl laughing and flirting with young man at bar
Image via mego-studio / Freepik

In that moment, finding the best questions to spark a fun, interesting or (dare I say it) even flirtatious conversation can be a struggle.

But the good news is that it really doesn’t have to be.

Whether you’re on a first date or talking to a girl you just met at a party, there are a ton of questions to ask a girl that will get her talking—and help your heart return to its normal rhythm.

Scroll down to find dozens of interesting questions to ask a girl in (almost) any situation, or use the Table of Contents below to navigate to the best questions for various scenarios.

94 of the Best Questions to Ask a Girl

The Ultimate Guide to Getting Girls Talking

Qualifying Questions to Ask a Girl You Just Met

Young attractive couple talking in cafe

Finding the right questions to ask a girl you just met is tricky because… well, you just met her!

You don’t know her yet, so you don’t know what she’s interested in.

Of course, in a perfect world, you wouldn’t just ask her about topics she’s interested in, you’d ask her about topics that make her light up when she talks about them.

But since you barely have enough surface-level info to go on at this point, you definitely don’t have the deeper knowledge about her likes and dislikes that will really engage her in conversation.

While that kind of insight would certainly be helpful, the good news is that it’s actually not necessary.

The below questions will help you spark conversation topics that will get her talking, thinking and sharing…

…which is the best way to help you learn more about her, and make the conversation better.

How do you spend your time?

This is way better than asking “What do you do for work?”

Phrasing it this way allows her to talk not just about her job, but also about her hobbies, which she’s probably more passionate about.

Would you rather be famous, or rich?

This is a great question for understanding her motivations. Is she more interested in the attention of fame, or the luxury of money?

Is it wrong for girls to first make the move in a relationship?

Slightly polarizing questions like this one make for good conversation starters.

Plus, it’s a great way to start learning about her thoughts on relationships.

Do you have a celebrity crush? (And if so, what do you like about him?)

This is a fun question that gets her talking about something (or more accurately, someone) she’s passionate about, and gives you some valuable intel on her type.

What do you prefer: dinner out a nice restaurant, or a good home-cooked meal?

This one gives you a sense of whether she’s more of a nightlife kind of person or a homebody.

What’s your idea of fun?

This question has two advantages:

First, it puts her into a fun mindset as she starts thinking through what to say.

Second, it reveals something about how she likes to spend her free time, which you can store for later.

How do you know the host/(our mutual friend)?

This one is great for when you meet a girl at a party and social gathering.

Where do you fall on the introversion/extroversion spectrum?

This is a great question for getting her to talk about herself and her personality, allowing you to find out if you think it matches with yours.

If you could live anywhere in the world, where would you choose?

Spark a fun fantasy as she daydreams about another life, and learn about what she considers “ideal.”

Who are your heroes? Who do you admire most?

This one is really revealing because the people she chooses will tell you a lot about her. It’s also great for sparking follow up questions:

  • Why did you choose (that person)?
  • What personality traits do they have that you admire?
  • What makes you admire (those traits) so highly?
Other than English, what do you think is the most useful language for a person to speak?

This is a great question if you’re interested in current events, because it sparks all sorts of interesting conversations about what makes a language “useful,” which countries/languages are on the rise, etc.

What does your ideal weekend look like?

This is another way to find out about the hobbies and activities she does in her downtime (and is likely most passionate about).

Plus, it also gives you some ideas you can store away for potential future dates.

What was your favorite movie of the past decade?

Movies are a great topic when you’ve just met someone because almost everyone has a favorite.

And since her favorite is almost certainly different from yours, it can lead to lots of great opportunities for discussion and debate.

Questions to Ask a Girl You Like

Smitten man looking at cute girl on bench

With due apologies to firefighters, for my money, talking to a girl you like is damn near the bravest thing a thoughtful and introspective guy can do.

When you really like a girl it can be hard to think straight and easy to get flustered, all of which makes it harder to come up with questions that will get her talking.

You basically get all of the usual pressures of talking to a girl that I described above: beating heart, sweaty palms, all the nerves.

PLUS the added pressure of feeling like your heart is on the line and there’s a lot to lose if you ask the wrong questions.

Fortunately, you don’t have to worry about that.

(I know my saying that probably won’t make you believe it, but I swear, it’s true!)

Jot down a few of your favorites from the list of questions below and keep them in your phone so you can easily reference them before you interact with the girl of your dreams.

Each of them will help relieve you of the pressure you feel to say the perfect thing, and make it easier to have a natural (and naturally engaging) conversation with her.

What’s one thing that you just couldn’t live without?

As she narrows down her list in her head, this question gets her thinking about all the important and interesting things she values most in the world.

And since you’re the one who asked her about them, she’ll subconsciously associate you with them.

If you could have any super power, what would it be?

Now that superheroes are a mainstay in movies and pop culture, this one will seem a lot less nerdy than it would have 20 years ago.

Plus, it’s a light, playful question that can open up all sorts of avenues for fun conversation.

What’s the most memorable dream you’ve ever had?

Asking her to recount her most memorable dream means inviting her to tell you a story that she’s probably told to very few people before, which creates a bond between you.

Whether it was a scary nightmare, a crazy adventure or (if she doesn’t mind revealing it) a sexy encounter, it’s a great way to spark some fun conversation.

What’s the most embarrassing thing you’ve ever done?

We can often be very intimidated by the girls we like.

So asking her to tell you about the worst thing she’s ever done or the most embarrassed she’s ever been is a great way to remind yourself that she’s human too, and has probably stuck her foot in her mouth just as often as you have.

But be warned:

Once you ask her to tell hers, she’ll probably ask you to reciprocate, so only ask this question if you have an embarrassing story of your own that you’re willing to share.

What do you find the most intimidating?

This is another take on the “most embarrassing” question above that lets her save face:

Instead of telling you about a time she felt embarrassed, she can talk about something that intimidates her.

For you, the effect will be the same: it will help you see her as less perfect and more like any other person.

Do you remember your first kiss?

Pretty much everyone remembers the first time they kissed, but most people don’t feel too sentimental about it.

That makes this is a good question for tip-toeing into more romantic territory without making it too obvious that that’s what you’re doing.

What was your New Year’s resolution this year?

This question does double duty:

On the one hand, it gives you a sense of her goals, priorities and aspirations for herself.

On the other hand, it again helps you see her as a human being with flaws, because almost everyone gives up on their resolution by February.

What’s your happy place? Where do you feel most comfortable or happy?

This is a great question for getting to know her better, and another opportunity for her to think about something she cares about, and subconsciously associate it with you.

If you were a character on Friends, who would you be?

The best thing about this question is that it’s a sneaky way to learn a lot not just about her, but potentially about whether or not you have a good chance with her.

Both Monica and Rachel ended up with guys from their friend group.

So if you’re trying to move from the friend zone into a more romantic relationship with her, then either of those answers will indicate that she’s at least open to the possibility, in theory.

And if she says Phoebe, it’s…

…well, it’s yet another indication of how advantageous it is to be as damn handsome as Paul Rudd.

What do most people consider the weirdest thing about you?

This question is also kind of sneaky, because by asking her to choose what she thinks people consider weird about her, you’ll learn a little about her own insecurities.

What do you usually notice first when you meet someone new?

With this one, the key is to not let her get away with saying “Their personality.”

Ask her to be more specific: is it their sense of humor, how extroverted they are, how confident they seem?

What would you do if you won the lottery?

The answer to this one can be really revealing.

Would she quit her job and start a nonprofit to support her favorite cause?

Or blow it all on big mansions, fast cars and crazy parties?

The wide spectrum of answers means there’s a lot to learn here.

If you could give your younger self one piece of advice, what would it be?

This is an important question because it’s both insightful and revealing:

She gets to think about things she might have done differently, and you get to learn about what she considers important.

Stop Doubting, Start Dating
The Shy Guy’s Guide To Building Confidence, Meeting Women, and (Finally!) Getting the Girl

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Questions to Ask a Girl Over Text

Cute girl reading text in bed

Texting can be super fun, but it can also be kind of awkward because texting is less personal than an over-the-phone or face-to-face conversation.

And because of that disconnect, there’s a higher likelihood that your questions, tone or intention will be misinterpreted, turning what you think is fun banter into something she finds insulting or even off-putting.

Use the questions below to avoid falling into that trap, and spark some conversations that are fun, playful and engaging, but not controversial or likely to be misinterpreted.

What kind of music do you listen to?

This is a great question to ask over text because you not only learn about her tastes, but swap links to songs or playlists you like.

This is a great question to ask over text because you not only learn about her tastes, but swap links to songs or playlists you like.

What kind of trouble are you getting into (today/tonight/this weekend)?

Flirty questions like this will help you stand out, and help you strike up an ongoing conversation.

Most guys just text “What are you up to?” or – the even more inane – “Sup?”

Phrasing it around the “trouble she’s getting into” makes it more playful, which encourages her to be playful back when responding.

What three words best describe you?

This would be a weird question to ask in person because it would put her on the spot.

But over text she can take the time to think about her answers, and respond with a list that will give you all sorts of fodder for follow-up questions.

(e.g. “That’s interesting. In what ways are you impulsive…?”)

Have you ever been caught red-handed doing something?

If she’s shy or otherwise modest, this question might make her blush if you ask it in person.

But over text, she’ll likely feel more comfortable answering, and revealing something she otherwise might not.

If you could body-swap with anyone on earth, who would you choose?

This one’s fun because she’ll probably pick a famous celebrity, which can spark conversations about celeb gossip, the nature of fame, sci fi concepts like body-swapping, etc.

What’s the dirtiest joke you’ve ever heard?

This is another question she might feel more comfortable answering over text than in person.

It’s also one that you could potentially use to segue into some of the more flirty/dirty questions listed below.

What are your three favorite things in your house/apartment, and why?

This question is fun because it’s random. It breaks up the monotony of small-talk questions, which will catch her attention and likely prompt a response.

What is the most irrational fear you have?

Asking about her fears might bring up a topic she doesn’t want to think about.

But asking about an irrational prompts her to think about the nature of her fears, which can lead to some really fascinating discussions.

Be honest: how many selfies do you have on your phone?

Everyone has a few selfies, and some people have way more than a few.

Asking about how many she has will probably prompt her to go look in her phone and start counting them up, which creates a level of engagement that you don’t get from other small-talk type questions.

I’m bored. Any ideas?

Asking her to give you a suggestion for what to do is great because it gets her thinking both about you, and about fun activities.

If she gives you a good suggestion, it perfectly sets the stage for you to ask if she’d like to come join you in her suggested activity.

What’s the funniest video/meme you’ve seen online?

Another good opportunity for you and her to not only share some media, but a good laugh.

Even if you’re not the most naturally funny person, asking funny questions (or questions about funny things) will help her associate you with humor.

This gives you an easy way to score some points without having to deliver any jokes of your own.

Do yo believe in karma?

This is a good question because it seems “deep” without actually being very profound.

It’s a good way to dive a little bit deeper than just surface-level conversation, without getting into controversial territory like religion.

What’s the biggest challenge you’ve ever faced, and how did you overcome it?

Another question that moves you past small talk and into more substantive convos, this is also another question that she might be more comfortable asking over text than in person.

If she’s modest, she might not like to brag about her accomplishment, but over text she may be more willing to discuss it, and share something personal in the process.

Questions to Ask a Girl When Getting to Know Her

Couple having coffee and talking

After you’ve had a few initial conversations, or maybe even gone on a couple of early dates, it can be tricky to transition into that next phase.

You’ll probably want to get past the (fun, if superficial) small talk and into personal questions that are a little more intimate, and allow you to start getting to know her on a deeper level.

Making this shift requires using the questions below, which are revealing and a little more intimate, without feeling too prying or personally invasive.

What’s something that’s happened in your life that has made you a stronger person?

This question starts moving into the personal because it asks her about a challenge or trial she’s faced.

But framing it around the challenges that have made her stronger will make her feel good about telling the story—and sharing a lot about herself in the process.

Where do you feel most like yourself?

This is a simple question that actually reveals a lot.

If she feels most like herself while at home alone, then she’s like an introvert who needs alone time to recharge.

If she feels most like herself at a party with a big crowd, then she’s clearly an extrovert who loves to be around people.

Whether she feels most like herself at work, on the tennis court, on the back of her Harley (hey, ya never know), or anywhere else, you’ll learn a lot about her from her answer.

What’s one trait that you don’t have, but wish you did?

Reframe the typical (and at this point kind of boring) “What would you change about yourself?” question by asking her about the traits she wishes she had.

The answer will tell you just as much about her, but the question will feel less common to her, which will make you look even more insightful.

Which member of your family are you closest with?

Another great spin on a common question.

Most guys ask “So, are you close with your family?” But asking yes-or-no questions lead to yes-or-no answers, which don’t spark much conversation.

Asking which member she’s closest with opens up lots of possibilities for follow up “why” questions that will reveal a lot more about her:

  • Oh, you’re close with one sister but not the other? Why do you think that is?
  • Why do you think you’re closer with your dad than your mom?
  • You’re not very close with your family at all? Why is that?
Who’s the best friend you’ve ever had?

Like the family question above, this is one of those deep questions that allows her to speak about the nature of her relationship with that person.

This will reveal a lot about what qualities she values in a friend, and what friendship means to her.

Did you have a dream job as a kid? What did you think you’d be when you grow up?

This is a fun way to start talking about your respective careers, without having to resort to the boring “What do you do for work?” question.

Most people have childhood fantasies that go unrealized in adulthood.

In talking about why she veered off the path of an astronaut/lawyer/gymnast-turned-diplomat, you can get a sense of her educational and career path without having to ask about them.

Who’s your favorite fictional character of all time?

This question can lead to great discussions about her favorite book, movies or TV shows.

But it’s also revealing because it will give you a sense of what kind of media she consumes. Is she a deep reader? A TV addict? A film buff?

What’s your take on soul mates?

Another example of how rephrasing a common question can lead to better results.

Instead of asking the yes-or-no “Do you believe in soul mates?”, asking “What’s your take…” lets her expound on why she holds certain beliefs.

This makes her answer more revealing, and opens up lots of avenues for conversation about the nature of love, romance and relationships.

Be honest: what do you tell people is your favorite TV show/movie, and what’s your real favorite show/movie?

Ever wonder how shows like The Big Bang Theory can last for a decade and run for hundreds of episodes, while shows like The Leftovers can make critics’ lists of “the best shows of all time” but have less than a quarter of the audience?

It’s because everyone wants other people to think that their favorite shows are arthouse masterpieces, when in truth we all love some good ol’ fashioned cheesiness.

Showing her that you recognize this pretense and asking her to drop it for you will help bring you closer together (as long as you’re willing to reciprocate, of course).

What’s something you feel like your life is missing?

This question definitely moves into deeper territory and requires that you already have a pretty strong rapport.

But it’s one that can be really illuminating for both of you because it asks to think about her life in a big-picture sense, which she may or may not be used to doing.

Questions to Ask a Girlfriend

Couple holding hands and smiling

Once you’re in a relationship, the focus of your questions tends to shift from “sparking conversation” or even “getting to know you” and into “learning everything about you.”

The trouble is, at this stage you may feel like you’ve already covered all the ground you can think of – or feel comfortable asking about – and you don’t want to ask questions that might disrupt the good thing you have going.

The questions below will help you keep the lines of communication with your girlfriend open, without veering into territory that neither of you is comfortable revealing at this stage.

How do you feel about marriage?

Whether or not she perceives as a serious question depends on how you approach it.

Asking “Do you want to get married?” is a little too close to the question “Will you marry me?”, which makes guys understandably hesitant to ask it.

Rephrasing it to ask how she feels about the concept of marriage in general will get at the same topic, but without the (potentially heavy) implications.

What’s your favorite charity?

This one helps you better understand what social causes she values, which will also give you a good sense of her overall value structure and beliefs.

When you’re gone, what do you most want to be remembered for?

This question is admittedly a little dark, but it’s also helpful for getting a better understanding of how she sees the big picture, and finding out what she considers to be the most important thing in her life.

Can you think of a time when you faced discrimination?

Unfortunately, for most women the answer to this question is “yes.”

And while it can sometimes be uncomfortable to talk about, understanding the challenges she’s faced will give you a better perspective on what she’s been through, while making you more empathetic in the process.

What’s your greatest fear?

Another one that’s a bit dark, this one is also incredibly revealing.

Her greatest fear could be as minor as “spiders” or as heady as “not living up to my full potential.”

Understanding which end of the spectrum she falls on will tell you a lot about her.

What does relaxation mean to you?

When you first start dating, so much of your time is spent doing fun activities.

But as your relationship matures, a lot of the time you spend together is actually down time.

So learning how she likes to relax – and making sure it matches your own preferred methods for relaxation – is actually pretty essential to a healthy relationship.

How do you feel about guys giving girls flowers?

This is yet another example of asking a non-standard question to learn something important.

If you just ask her “What’s your favorite type of flower?” then she will 100% expect that the next time Valentine’s Day, her birthday or your anniversary rolls around, that’s what she’ll get.

But by asking her about the very concept of giving her flowers, you can spark a conversation in which you can find out what flowers she likes, without over-playing your hand.

(e.g. “I agree, it is corny when they hand out roses on The Bachelor. Do you think it would be less lame if they used a more unique flower? What would you want to be handed if you were on that show?”)

What’s one trait you have that most people don’t see?

Everyone knows something about themselves that others either don’t or can’t see.

Asking your girlfriend about hers will bring you two closer together, and allow you to know her in a way that no one else does.

Are you more of an urban person, a suburbs person or a country person?

This is another one that helps you learn valuable information, without any unwanted implications.

Asking something like “Where do yo see yourself living in five years?” implies that you’re already doing some long-term planning for the two of you, which may or may not be well received.

But asking what kind of person she is will allow you to find out whether her preferred living situation matches yours.

What was the best job you ever had?

When you first meet someone new, so much of your conversation focuses on the present:

What do they do for work, what do they do for fun, how long have they lived in town, etc.

But as your relationship progresses, asking questions about her past allows her to reminisce, and you to paint a fuller picture of how she became the person she is today.

 What was the best wedding you ever went to?

Most of us go through a period where we find our summers booking up quickly as our friends and relatives start getting married.

Asking your girlfriend to share some of her favorite wedding stories can be a fun way to learn more about what kind of shenanigans she and her friends have gotten up to in the past.

And much more importantly, it’s a good way for you to learn about the elements that she thinks lead to a great wedding (information that could come in handy down the road…).

How many boyfriends have you said “I love you” to?

Talking about a past relationship is fairly common in the early stages of dating, but it’s usually more quantitative than qualitative.

You might talk about how many people you’ve each dated, but you’re not likely to describe the nature of each relationship in great detail.

But as your relationship grows, you can begin asking more substantive questions to get a better sense of what her love life has been in the past, which will likely inform what she wants it to be in the future.

Have you ever been to a surprise party?

Much like some of the other questions above, this is really a question about her preferences disguised as a question about her experiences.

In answering, she’ll likely let it slip whether or not she likes surprise parties, which is more info you can file away for later.

Flirty & Dirty Questions to Ask a Girl

Topless couple kissing on floor

One of the (many) advantages of getting to know a girl well is that, at a certain point, you transition from small talk into questions that are flirtier, sexier, and – assuming you’re both into it – even dirtier.

The trouble is that transitioning from small talk to sexy talk is hard to pull off, even if you’re doing it over text.

Guys are often not sure what kind of dirty questions to ask a girl, how vulgar to be, how far to go, or how to even get the ball rolling.

Below are some hot questions to ask a girl that you can use to spark some sexy conversations. Then, use her answers to gauge whether or not she’s as interested in pursuing this kind of conversation as you are.

If she is, then ask a few more.

But if you get even the slightest hint that she’s not, it’s best to pump the breaks and refer to some of the earlier questions on this list, which will help you build more rapport, trust and comfort with each other.

What celebs would you put on your “hall pass” or freebie list?

Ever since an episode of Friends popularized the idea back in the ’90s, people (and especially women) have loved fantasizing about the celebrities they’d be “allowed” to cheat on their partners with, if they ever met them in real life.

This can be a fun way to segue into talking about sexual desire and fantasies without getting too graphic right upfront.

What do you think is your sexiest physical feature?

Talking about her body is a high-risk maneuver, but when you ask a question about what she finds sexy about herself, you create space for her to feel comfortable talking about her physicality, while making her feel sexy in the process.

Would you ever go skinny dipping?

Skinny dipping isn’t necessarily sexual, but the act of stripping down at night to jump in the water can often be sexually charged.

So this question can start tilting the conversation toward sexuality by first introducing the topic of nudity, and gauging whether or not the topic is in her comfort zone.

Where’s the funniest or strangest place you’ve ever had sex?

Asking about some of her past sexual experiences is a good way to start a more sexually charged line of conversation.

And starting with something novel like the funniest place she’s done it will let you both ease your way into it.

How long do you think you could go without having sex?

As you begin moving into more obviously sexual topics, this is a great question for gauging both the level of her sex drive, and her interest in answering more sexually focused questions.

What’s the sexiest quality a man can have?

For guys, sexiness is often (and in some cases, almost exclusively) about the physical. For women, it’s often about the mental and emotional as much  as the physical.

Asking about sexy traits or qualities will show her that you understand the distinction, while encouraging her to talk about her turn ons.

What’s your favorite place to be touched?

This question starts to move into the realm of the physical, but keeps the emphasis on her and what she likes.

This gives you valuable information, while signalling that you’re generous with your touch and focused on her pleasure.

Have you ever had a one-night stand?

Another question about her past, this one allows her to recall a time when she might have done something impulsive, which, though obviously potentially dangerous, can also be sexy and fun to recount.

What’s the sexiest outfit or piece of clothing you own?

Talking about sexy clothes can lead to both thoughts and discussions about where and when to wear them, which open up all sorts of scintillating possibilities.

What was the naughtiest text you ever sent?

A lot of people find it easier to talk about sexy or dirty things over text.

If you’re not sure whether or not she’s comfortable talking about sex in-person, you can get a sense of her comfort level by asking about whether or not she’s had naughty conversations via text.

Do you have any sexy guilty pleasures?

If she trusts you enough to reveal her answer to this question, it’s a sign of strong (and potentially sexy) intimacy.

Whether it’s a penchant for romance novels that she tries to keep on the down low or a kink she only shares with trusted partners, just be sure to remain nonjudgmental.

And be willing to reciprocate with honesty of your own.

What are your three biggest turn-ons?

As you get more comfortable with each other you can move into more explicitly sexual questions.

Asking about her turn-ons is as direct as it gets, and can be a fun way for you both to get turned on just by talking.

How often do you pleasure yourself?

Getting even more explicit, asking her about her self-pleasuring habits obviously requires a ton of comfort between you two.

But if you get the sense that she’s open to answering, it can supercharge the conversation.

How to Level Up Your Dating Game

You know some questions to ask a girl. Next up? Feeling confident enough to ask them.
Stop Doubting, Start Dating

For thoughtful guys who want to strike up fun, memorable and maybe even meaningful conversations with women, knowing the best questions to ask a girl is an excellent first step.

But as any guy who’s felt nervous talking to women knows, knowing the questions is really only piece of a (much) larger puzzle.

While knowing the right questions to ask definitely helps, the real key to improving your conversations with women is improving your confidence with women.

In my book Stop Doubting, Start Dating I’ve laid out the exact process I used to do just that. The book outlines a proven formula that shy, quiet and thoughtful guys (which is to say, guys very much like myself) can use to build more confidence, meet more women, and get more dates.

Pick up a copy of Stop Doubting, Start Dating to learn the secrets of romantic success.

Buy Stop Doubting, Start Dating

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About Dave Bowden

Dave Bowden

Founder, Irreverent Gent
Author, Man in Command and Stop Doubting, Start Dating
Writer, Really Wordy Author Bios

Dave Bowden is a style blogger, menswear expert and best-selling author (in Canada—but still!) whose advice on how to look good and live well has been featured in New York Magazine, The Wall Street Journal, Men's Health and more.

When not obsessing over style and self-improvement, he can usually be found spending time with his wonderful wife and two amazing sons, indulging in a hoppy craft beer, or sobbing over the woeful state of Toronto's sports teams.

Check out Dave's Style Story to find out how a chance encounter with his friend's step-dad taught him the value of looking good and living well (don't worry—it's less creepy than it sounds!), or email him at [email protected] if you want to get in touch.

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