100 Engaging Questions To Ask A Girl You Like


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Having an repertoire of fun, interesting and personal questions to ask a girl you like will give you more confidence to talk to her.

When you meet someone special you might want a relationship with, you should strive to know her on a deep and personal level. This makes communication an essential relationship skill to master.

However, while most men could use some help with the ladies, few are willing to put in the work.

If you are tired of the same old small talk or just never had the confidence to strike up a conversation, you did good coming to Too Manly. We have put together a comprehensive list of over 100 engaging questions to ask a girl (the girl!) you want to know better.

Best Questions To Ask A Girl

Although most of the questions can be great as standalone questions, holding an effective conversation necessitates asking follow up questions. So go through our list and load up your arsenal with as many as you can.

Take what you need for situation, and come back for the rest later. Let this collection be your number one source of great questions to ask a any girl you might be interested in.

Get To Know Her: 10 Personal Questions to Ask A Girl

Inquiring about her favorite color and food can only take you so far, and that’s because such questions are too basic. To truly get to know a person better, you have to dive deeper.

Asking personal questions can do the trick, but timing is key. The last thing you want is for her to misconstrued your questions as intrusive, if not creepy.

Here are 10 of our favorite personal questions to ask a girl you really want to know.

1. What is the best and worst part of your personality?

This question is surprisingly difficult to answer because people don’t make the time to reflect on who they are and how they are perceived.

She might be astounded by how little she knows about herself, so give her time to think about it. Help jolt her mind by asking other personal questions.

2. What do you hope you grow out of?

Renowned German philosopher Nietzsche once said “In every real man and woman a child is hidden that wants to play.” It’s difficult to argue with that, but although our inner child can be a source of great happiness, there are some “childish” tendencies people wish they can outgrow.

Be it getting on the back of a shopping cart and riding it like a scooter, getting tucked into bed at night, or laughing when the ketchup bottle makes fart noises, there is probably something she should have grown out of a long time ago. What is it?

3. What is the healthiest and unhealthiest thing you do on a regular basis?

In a world obsessed with everything being “bad” for you, we often fail to notice and acknowledge the good and healthy things we do.

It’s almost a sure bet that not getting enough sleep or exercise, eating too much unhealthy food, and spending too much time in front of a screen are among the unhealthiest things she does, but what are her healthiest?

4. How much do you judge a person by their appearance?

This is one of the best personal questions to ask a girl to gauge if she finds you attractive.

Conventional wisdom would have you believe that judging someone on appearance is not OK, and while that is a principle we should all strive to live by, there is something to be said about why nature designed humans to judge. This is a thought-provoking a topic worthy of discussion.

5. What are some things you would you like to achieve before you die?

Life is short, so what are the things she wants to achieve in the little time she has on earth?

Whether it’s adrenaline based adventures, traveling the world, buying a house, or sampling a unique local delicacy for the first time, expect her to share some of her life goals. See if you share any commonalities with them.

6. How would your perfect partner treat you?

There is no such thing as the perfect partner, but there is such a thing as an ideal partner.

Such individuals have developed themselves in ways that go beyond looks, charm and success, ways that are compatible and complementary to the significant other’s life and personality. This is one of the best personal questions to ask a girl to gauge her interest in you.

7. What dumb thing did you believe for a really long time?

Bread crust is more nutritious than the rest of the bread, babies come out of the bum, the earth is flat — these are examples of the crazy things many people use to believe or still believe.

Most of us learn the truth at some point and are better off for it, so what dumb thing did she once believe that she now laughs about? Also share yours.

8. What was the worst date that you’ve ever been on?

One way to find people to have a relationship with is to “date.” Sometimes these dates turn out well, often times they turn out boring, creepy, hilarious, or all of the above.

Chances are if she’s been on least one date, she’s also been on a bad date. Get ready to laugh or cringe.

9. What kind of parent would you like to be?

If you end up having children, they will be your legacy. How you raise them affects their performance academically and professionally; their habits, good or bad; their mental and physical health; and their contribution to society.

According to psychologists, there are four main parenting styles (autocratic, authoritative, permissive, and unengaged), each differing in the level of your involvement in your child’s life and how much control you try to exert over his / her behavior. What’s her style? What’s yours?

10. Who’s been the biggest influence on your life and decisions?

We are shaped by the people we interact with, and some individuals in particular can transform our lives in ways we don’t expect.

Granted that, unlike a hero, an influential person isn’t always a positive example, who is the person that impacted her life the most?

12 Interesting Questions To Ask A Girl

According to science, fluid conversations create feelings of social validation and belonging, and boost self-esteem. Do you know what helps create fluid conversations? Intriguing and interesting questions.

Asking the right ones will allow both you and the girl to deeply share your experiences and perspectives on life and learn more about each other. Here are our favorite interesting questions to ask a girl.

1. What is something that most people learn only after it’s too late?

Most people don’t reflect on their life journey, let alone the life lessons they will learn when they’re old. Sometimes, it’s very painful to think about such things.

Not only is this a good question to get her to reveal her biggest regrets in life and the changes she wants to make moving forward, but it will also allow both of you to reflect on your miscalculations through discussion.

2. How do you feel about cars becoming fully autonomous and having no steering wheel, breaks, or accelerators?

If you’re like most men, you have a strong appreciation for cars, at least more so than the average woman.

Chances are she knows little to nothing about cars, but this question will give her the opportunity to ask you questions about something you care about.


3. If could choose only one long-term goal, either to own a house or to travel the world, which would you choose?

This is one of the most binary and interesting questions to ask a girl because there are only two options.

Her answer will say a lot about how adventurous she is, not that there’s anything wrong with being a homebody.

4. Besides food, water, medicine, or money, what would be the most helpful thing to airdrop to refugees of a war torn country?

Yes, this is one of those Miss Universe beauty pageants kinda questions, but it can speak volumes about her worldly knowledge and about her character.

Will be it be weapons and ammunition so that they have the power to fight back? Perhaps a genie in a bottle to wish away all their suffering? It is certainly a thought-provoking conversation-starter.

5. If you didn’t have to worry about money, what would you do all day?

For most people, success equates to earning as much money as possible, and this often leads some to resort to despicable means to earn just a few bucks. Is this healthy?

What would she do differently with her life if money wasn’t an issue? Bask in the sun all day? Donate her time to a humanitarian cause? Perhaps build or create something?

This question can help you assess what she wants in life.

6. When does time pass fastest for you, and when does it pass the slowest?

This is one of the best questions to ask a girl to get to know what she enjoys and what bores her. We all have something we love so much that we could spend every waking second doing if possible.

If she can’t come with any, list out some activities to see which ones bore her to death and which ones make time fly.

7. What do you wish people would stop asking you?

We all have someone who asks us the same questions over and over again. Whether it’s about your future, life circumstances, or personal things, these questions can become annoying, if not infuriating.

She might get a bit emotional when answering this one, so brace yourself.

8. Where is the last place you would ever go?

This seemingly simple question requires a lot more thought than you would think, and there is no telling how she will answer with it.

Her response can be creative or it can be very literal; it can be funny or serious.

9. If you could slow down time, what would you do with it?

This is definitely one of the most interesting questions to ask a girl because, while not everyone wants to live forever, no one wants to feel constrained by time.

Ask this question to a girl if you want to know the people, things and activities she cherishes the most.

10. What’s the craziest or most out-of-character thing you’ve ever done?

You would be surprised at the crazy things some people will do for an extra suck, let alone a million dollars. But it’s not always about money.

Sometimes it’s due to peer pleasure, while in many instances it’s feeling compelled to do unpleasant things you detest, such as wasting valuable time and energy on a job you hate.

While she probably won’t tell you the crazy things she did in Cancun during spring break, her answer will likely be interesting.

11. If you could relive one day from the past, which would it be and why?

This question brings to mind Groundhog Day, the 1993 movie where Bill Murray is forced to relive the same day over and over.

If either of you could choose to relive one day of your life, what would it be? Would it be a fun vacation, a memorable experience with a loved one who passed away, or perhaps doing something over and getting it right this time? The possibilities seem endless.

12. If you were stranded on a desert island, and could only have one book, one piece of clothing, one food item, what would they be?

We’ve all heard the question in one form or another. It’s a fitting addition to our list of interesting questions to ask a girl because it is an excellent icebreaker that can reveal a lot about a person’s deeper character traits.

Her answers can range from the practical (e.g. a canteen of water, a non perishable food item) to the creative but slightly ridiculous (e.g. an endless supply of chocolate).

13. If you could invite ANY three people from history over for a dinner party, who would you invite and why?

It’s an interesting question you may have heard before, possibly at a job interview.

Not only will it give you a sense of who she really is, but can also help you assess her level of self-awareness.

14. At what age do you think a person needs to “grow up”, and why?

Here at Too Manly, we are a firm believer that age is just a number and that you are as old as you feel. Despite this, an interesting survey out of the United Kingdom found that young people don’t believe they have become a “grown-up” until they reach the age of 29.

Does she agree with this? If not, why? Better yet, what does it mean to “grow up”, and does she consider herself to be grown-up? This topic can make for a very engaging conversation.

Need help being an all-around interesting guy? Watch this video:

11 Deep Questions To Ask A Girl

These are the type of questions you ask a girl who you know quite well, or is at the very least into ethics, philosophy, and doesn’t shy away from critical thinking.

Although far from light and fluffy icebreakers, they can be very personal and help build trust. Here are our favorites.

1. What’s the biggest lesson life has taught you?

This is one of the most serious questions to ask a girl, but an excellent conversation-starter nonetheless.

We have all learned many great lessons throughout life, lessons that have shaped who we are. This is your chance to learn more about how she became the person she is.

2. How important is family to you?

The concept of “family” goes beyond bloodlines, last names or obligations, and it can mean different things to different people.

Use this question to gauge what she values in a relationship and how well she gets along with her family, if she has one. It can also segway into questions about specific family members.

3. If you could be a fly on any wall, where would it be and why?

Omnipresence is a power most people wish they had. What is something throughout history or in her own life that see badly wants to see, and why?

Her answer might reveal an internal conflict and possibly her inner geekness.


4. How often do you see your good friends?

Friendships take time to develop. The more time you spend with someone, the more likely he or she is to become your friend.

Moreover, people are the company they keep, and our friendship habits can say a lot about our personalities, likes and dislikes, and more. How many friends does she have, and how close is she with them?

5. Would you like to have kids at some point in your life?

One of the most common questions to ask a girl. There are those women who can’t imagine a life without kids, and then there are those who see children as too much of a financial, physical and emotional sacrifice.

”What’s the point of having kids if your life ends when theirs begins?” some would argue.

See which camp she falls into and what you can learn about her perspective on life as a woman.

6. What are the three principles you would want to pass along to your children?

As Franklin D. Roosevelt once said, “We may not be able to prepare the future for our children, but we can prepare our children for the future.”

This one can serve as a follow-up to the previous question. If she wants to have children, the values and principles that she wants to impart are hopefully those she shares.

Don’t forget to chime in with your viewpoints to keep the conversation flowing.

7. What is one thing you think about a lot when you’re alone?

Every single question on our list of questions to ask a girl will give you a peek into her mind, but this one takes aim at the deepest recesses of her psyche.

Is the thing she thinks about profound? Is it mundane?… Is it weird?

8. If you could change one thing about your personality, what would it be?

This question is a variation of the weakness question people often get asked in job interviews. It will help you evaluate her self-awareness and ability to admit to aspects of her life that she would like to improve.

No one is perfect, after all. If she presents herself as someone who has no flaws, it’s probably best to cut short your interaction with her

9. When you were little, what did you want to do when you “grow up”?

“What do you want to be when you grow up?” is a question she may have heard a lot as she was growing up. Now that she’s older, she can look back and reminisce.

Naturally, you’re going to want to know if she became what she wanted to be as a kid, and this should lead to a deep conversation about her personal and professional life.

10. Who’s been the biggest influence on your life and decisions?

This is one of the simplest questions to ask a girl yet one of the hardest to answer considering all the fascinating people we encounter.

Thinking back to the people, events, and ideals that inspired her can be introspective and surprisingly motivating, likely resulting in a great conversation.

11. What’s been your biggest mistake and what did you learn?

Yes, this one sounds too much like a job interview question, but aren’t all the questions on this list basically interview questions? I digress.

We all make mistakes, and that’s not a bad thing. Success involves making mistakes and rapidly fixing those mistakes.

10 Weird Questions To Ask A Girl

Having some weird questions to ask a girl can certainly spice up your interactions and also give her inner weirdo a chance to shine.

Here is a collection of very unusual questions that should keep her on her toes. Just don’t be surprised if you get some strange looks.

1. When was the last time you screamed at the top of your lungs?

People don’t usually scream for no reason, so this question is sure to lead to an interesting story.

There is a good chance it has something to do with what a sibling did, but what if it was someone else that got her so angry, someone like an ex?

2. What would your dream bathroom look like?

What are the odds she’s even been asked this question? Slim to none, if you ask me.

She’s probably never even thought about, so give her some time to see what creative things she can come up with.

3. What was the weirdest conversation you have overheard?

There are some many conversations going on at any given time that it’s virtually impossible to go through life without overhearing several. These conversations are even weirder when there is no context.

So ask away and have a good laugh at the weirdness that surrounds us.

4. What was the most magnificent fountain you’ve seen?

One of the most random and weirdest questions to ask a girl for sure. How often do people think about fountains, let alone the ones they’ve seen?

Assuming she hasn’t been to a place sprawling with fountains (e.g. Las Vegas), expect a long pause after asking this questions.

5. What food would be the best to make a house out of?

It doesn’t get any weirder than this, folks. Your lady friend will definitely get a Hansel and Gretel vibe from this question, assuming she knows what Hansel and Gretel is.

Like the queen in the classic fairy tale, she’ll get to choose what foods to construct her house out of. See if she goes practical or delicious.

6. What is the ugliest thing you own?

People are used to getting asked about the nice things they own, so why not subvert her expectations?

7. What view would you most like to have out of your window?

One of the least weird questions to ask a girl, but still unusual.

She will definitely conjure up beautiful images of nice sceneries and possibly even recall some wonderful experiences.

8. What’s the most uncomfortable thing you’ve had to do out of politeness?

We have all done something we didn’t want to do out of politeness, so this question lets you find out what cringe worthy thing(s) her polite self has done.

9. Where’s the weirdest place you’ve found something that you lost?

We’ve all done it. You know, such as putting something like our keys somewhere they shouldn’t be because we were dead tired or in a rush.

You might get a chuckle out of the weird and embarrassing places she has placed stuff.


10. What’s the worst thing a person can do that isn’t illegal?

Now, this odd question is interesting in that her answer can be lighthearted and funny or outright serious.

Society is full of grey areas and moral ambiguities, so much so that she might inadvertently reveal a darker side of her personality.

16 Fun Questions to Ask a Girl

Asking a girl fun questions can lead to all sorts of interesting activities, such as arm wrestling each other.

You can’t blame girls for wanting to be with a ‘fun’ guy. Afterall, fun people energize others, while boring or negative ones drain them.

So why not give the ladies in your life more of what they want? Here are some fun questions that will help you show your lighter side so that they show theirs.

1. What is the silliest recent fashion trend?

Fashion and style is important to your success, but fashion and style trends can sometimes be silly.

This question will not only get her creative juices flowing, but it also allows you to get her perspective on what constitutes good fashion and style. Make the conversation even more interesting by asking her what she thinks about how you’re dressed.

2. What science fiction technology do you wish existed?

Why do men love science fiction so much? The answer is simple: Guys like to create on a grand scale, be it with their hands or with their mind.

Finding a girl who likes science fiction as much as you do is difficult, but not impossible. Asking this question and seeing how far she goes with it can be a litmus test of her appreciation for robots, spaceships, aliens, and lightsabers.

3. If you could replace the handshake as a greeting, what interesting new greeting would you replace it with?

A silly question if ever there was one, but a potentially fun one. Just imagine the two of you humorously trying out different greetings.

High fives with elbows? Something even more intricate? Let your imaginations run wild.

4. What is the most unusual fear you have?

This is one of my favorite questions to ask a girl because people generally like answering it and their answers can be really funny or really weird.

You might even find that you share her unusual fear

5. What would be your strategy for surviving an apocalyptic epidemic?

Yes, it’s a post-apocalyptic question, but considering the popularity of post apocalyptic shows, movies, and books, can you blame us?

Discussing the merits of each strategy compared with each scenario can make for a fun conversation, especially if you’re both into the post apocalyptic genre.

6. If your life had a mascot, what would it be?

Does this mascot reflect who she is? Her specific interests, talents or skills? Her ideal self? Or perhaps her hopes and dreams?

Her answer to this question will certainly give you an idea of who she is as a person.

If she chooses Baby Yoda as a mascot only because he’s so damn cute, give your dark side free rein to force choke her.

7. If you suddenly found out that your internal monologue for the last week was audible, how screwed would you be?

The nicest seeming girls can sometimes have the foulest, most deranged or , hopefully, most beautiful minds, so never judge a book by its cover.

She probably won’t tell you want exactly goes on in her head, but this question could spark a fun conversation and might give you a little peek into her soul.

8. How much would you pay to stop a hacker who threatens to release your browsing history to everyone you know?

If you had access to her browsing history, you wouldn’t come to Too Manly for questions to ask a girl. You will know more about her than you need to.

The amount she’s willing to pay the hacker might say a lot about the tantalizing things she’s into.

9. What always sounds like a good idea at the time but rarely is?

I can almost guarantee that this fun mental exercise will result in some rather humorous examples, with the two of you sharing good stories about your bad decisions.

Let loose. See who has the craziest tales.

10. What are some of the telltale signs that a guy is creepy?

We all know people who appear a bit creepy, but not many of us stop to think about the mannerisms that constitute creepy. Are they genuinely creepy or just a little socially awkward?

This is a topic girls often talk about with each other, so you can bet she has a lot to say about it.

11. What’s the best comeback you’ve ever heard?

A really fun, often funny question to ask any girl. She likely has a good story about an amazing comeback to share, and you probably do as well.

I mean, is there a person alive who doesn’t like hearing about a savage comeback?

12. What is the silliest reason someone you’ve known has completely lost it?

People can be unpredictable. Just when you think you know someone, they do or say something that makes you scratch your head or question why he or she is in your life.

This question is sure to pull out a good story out of her, and I’m sure you also have a funny story about someone losing it for no good reason

13. Who is your favorite actor or actress?

This is one of the most generic questions to ask a girl, but it’s perfect for learning what types of movies she likes.

Not only can it lead to an engaging conversation if you also like one of the actors or actresses she mentions, but it can also be spun into a discussion about movies.

14. What doesn’t exist but you desperately want or need ?

Perfect for blue sky brainstorming and some creative answers.

Imagining solutions to problems and the form they will take is always fun. Plus, you and her get to discuss problems that currently don’t have a solution.

15. What is your very first memory?

Few people can remember anything that happened to them before the age of 3, but that’s just a fraction of their life.

As far questions to ask a girl go, you get to listen to her talk about herself in the sincerest manner possible.

16. What is quite possibly the most annoying thing ever?

We all have something that annoys us, so what’s hers? If you really like her, it’s a good idea to try and avoid doing the things she finds annoying.


You might even find that there is something you both find annoying.

17 Funny Questions To Ask A Girl

Everyone likes to laugh, so it helps to have some questions to ask a girl you want to endear.

It’s true, laughter is the best medicine. Studies have found that a good laugh actually improves your health by triggering healthy physical and emotional changes in the body.

Victor Borge put it best: “Laughter is the closest distance between two people.”

Here is a collection of funny questions to ask a girl. Used them to get some good laughs.

1. What would be the first thing you would do if you woke up tomorrow as a guy?

Men and women can be so different that they might as well be different species. Although girls often joke around with stereotypes about men, she will never truly understand the way we act 100 percent of the time.

So, indulge her. You are bound to get a laugh out of it.

2. Who’s the worst guest you’ve had in your house and what did they do?

We have all been there. You invite someone over thinking they are a perfectly normal human being only to find out that they are Lucifer incarnated.

Asking this question will give her a chance to break out one of her funny stories. Encourage her with follow-up questions that seek more details.

3. What’s the most ridiculous argument you’ve had?

Stupid arguments are impossible to avoid sometimes, but they can feel so good! You can bet this question will lead to a funny story and conversation, one you will both enjoy.

Don’t let it be one-sided — I’m sure you also have several ridiculous argument stories to share.

4. Have you ever been walked in on naked?

This is one of the most random funny questions to ask a girl. Most people have been walked in on while naked, so she’s likely has a story to tell.

What you’re really fishing for are the circumstances that lead to the incident and her reaction when it happened.

5. What was the weirdest punishment your parents gave you when you were growing up?

Anyone who had even REMOTELY strict parents can remember an assortment of “rules” their parents forced them to follow. Sometimes, the punishment for breaking a rule is so bizarre that you can’t help but to scratch your head or even laugh.


If her family is on the light-hearted side of the family dynamics spectrum, she’s sure to have a funny story to tell.

6. What makes you feel the most awkward?

Awkwardness can strike anyone in the wrong circumstances, but not everyone gets awkward over the same thing.

What are the chances that some of the things that make her feel awkward are funny or weird? Find out.

7. Are you ticklish?

This one can get you into trouble if she answers yes and you tickle her, but that’s probably what you want, right?

Ask her what her random tickle spots might be, gain her trust by promising her that you won’t tickle her at the moment, and then warn her that you might sometime in the future.

8. Can you do anything weird with a body part?

Many people can do some rather weird and strange things with their tongues, while others are able to do weird things with their legs or arms. If she’s one of those people, you would probably want to know so that you’re not freaked out when she does her “thing”..

You would be surprised at how many people find it hilarious when people do weird things with their tongues. See if you can impress her with some of the weird things you can also do.

9. If dolphins are so much like humans, do you think they get thirsty?

Yet another one of those random funny questions to ask a girl, but a very appropriate conversation starter if she happens to love animals.

Not only might it lead to some chuckles, but it might even cause her to search up the answer on her phone.

10. Have you ever kissed someone accidentally?

Who wouldn’t want to know if the person they like has ever kissed someone by accident? What are the circumstances that led to the accidental kiss? Does she regret the kiss?

She will almost certainly ask you the same question in response, so be prepared to answer. Some good laughs can come out of this.

11. What joke went way too far?

As a heads up, this one can get dark real quick depending on the story she decides to share.


Either way, you are likely in for an interesting story that could speak to her character.

12. What are your funniest or weirdest quirks?

All of us have quirks, and they could be as random as having a habit of bursting out in laughter at random things most people don’t find funny or wearing sunglasses all the time.

In fact, neither of you might think your habits are quirks until you ask each other. Get ready to laugh over how weird you both might be.

13. Do you sing in the shower?

One of the most common questions to ask a girl, and for good reason. Girls sure do love their music, and singing in the shower is a very common behavior.

Get an idea of her music taste by asking her what songs she likes and what she sings in the shower. Perhaps you sing in the shower too?

14. When in the shower, do you tend to use soap or shampoo first?

A completely random funny question that will catch her off guard, so much so that she might take a few seconds to think about the answer before wondering why the hell you asked it.

Keep at it! Keep her on her toes.

15. Have you ever tasted electricity before?

This random but funny question can be taken in two ways. First, you can use it as a clutch to kiss her and then ask if she felt the electricity; second, you can ask it just to be funny.

With the former, you might get slapped if you don’t know her too well. If the latter, you might want to know that people usually experience a metallic taste in their mouth for a few seconds after being hit by electricity.

16. What’s your funniest childhood memory?

An easy way to break the ice with a girl you like is to have her share her funniest childhood memories. If the two of you happen to go to school together, modify the question by asking what her funniest school or college memory might be.

Be ready to also share some of your funniest memories, and don’t feel ashamed to pull out some funny pictures of yourself as a kid or at school. It will encourage her to do the same.

17. What’s the most embarrassing thing you’ve said or done around someone you had a crush on?

There’s a very fine line between super romantic and super cringe-worthy. This might not be the best question to ask a girl you just met, but it can bring out a good story.


Just make sure to be ready for some cringe.

Being funny is a valuable skill that doesn’t come natural to most guys. If you weren’t blessed with a witty mind, here is a video that breaks down how you can develop a great sense of humor and make women laugh in 3 steps:

10 Flirty Questions to Ask a Girl

You don’t need me to tell you that girls love confidence. Do you know how confidence guys express their romantic interest in a girl? By filtering with her.

Flirting has received a bad rep over the past few decades, but it’s a completely natural human behaviour. It also has several health benefits, including boosting your immune system, reducing symptoms of loneliness, and relieving stress.

Provided that you can read her clues and know when to stop, feel free to flirt. Here are some of our go-to flirty questions to ask a girl.

1. What do you like to do the most when you’re alone?

This question has s**ual undertones, so you might want to know the girl for a while before asking it.

Then again, she might like reading when she’s alone. Try not to let your excited mind jump to conclusions.

2. Do you prefer boxers or briefs on a guy?

Boxer, briefs, or boxer briefs? While I’m sure you have a preference, you’ve probably wondered which one the ladies like best.

I can see this starting a passionate conversation that can lead to some rather “interesting” places.

3. What’s your opinion on kissing in public?

Everyone has varying opinions on how much PDA is OK, and this can lead to an engaging discussion..

However, the real purpose of this question is to gauge her openness to kissing you.


4. Have you ever skinny dipped?

Skinny dipping is not a big deal in Europe, the home of public nakedness, but the very mention of it in North America is enough to make a girl blush.

Fortunately, more and more people are warming up to nude swimming. Is she one?

5. Have you ever been caught doing something you shouldn’t have been doing?

Even though kissing is one of the simplest expressions of affection or arousal, it can be difficult to tell if you’re actually good at it.

Not only will this question give you an idea of how good of a kisser he is, but it will also let her entertain the idea of kissing you.

6. What do you think would happen if we were stuck in a room for 24 hours together?

This is one of the most daringly flirtatious questions to ask a girl. It requires so much confidence that the sheer audacity of it will either make her feel more attracted to you or turn her off entirely.

Either way, she will respect you for having the balls to even ask.

7. What are you most attracted to in a guy?

To trim or not to trim, that is the question many men often ask themselves, whether or not they admit it.

Men’s body hair is a touchy subject, and considering women have been dealing with it for ages, it’s bound to spark an engaging conversation that possibly prompts her to visually undress you.

8. What’s your guilty pleasure?

You’re hoping it would be something exciting and possibly even s**ual, but it could end up being something as mundane as having an extra scoop of ice cream or slice of cake.

Either way, you won’t know if you don’t ask.

9. Have you ever had a one night stand?

The one-night stand is so common in today’s hookup culture that you would be hard-pressed to find a girl who hasn’t had one. But that doesn’t mean unicorns don’t exist.

Heck, you might be dealing with one. Just don’t expect her to be completely honest with you.


10. Are you a shower or bath kind of girl?

Although showering is the main way most people get clean, almost everyone loves a good bubble bath once in a while, women seemingly more so than men.

What do women get up to when they’re in the bath, anyways? See if she can quench your curiosity.

Remember, guys, there’s a difference between flirting and being creepy. If you don’t know what that difference, watch this well-explained video by Charisma on Command:

11 Random Questions To Ask A Girl

Random questions can help you break awkward silences and throw your audience off balance so that they are more honest and genuine with their responses.

Here are some random questions to ask a girl to shock and jostle her so as to spice up your conversations.

1. What world famous monument do you have no interest in visiting?

A pretty random question that can lead to some interesting answers and give you an idea of her predilection for traveling.

If she happens to like traveling, she can share her most memorable experiences.

2. Who was the most power mad person you’ve met?

Kind of an odd question to ask anyone, let alone a girl, but it might lead to an interesting story.

There are a lot of strange people walking around these days, and we’re all likely to bump into one.

3. Would you rather have a lot of money or find true love?

Can money really buy happiness like many people believe, or is the saying utter nonsense? Interestingly, studies show that women associate money with love, while men link it to freedom.

She will almost certainly contest with the scientific findings, so brace yourself for a possible argument.

4. What’s your favorite day of the week?

Is she fun and outgoing, or more productive and mellow? Perhaps everyday is a Saturday for her.

Finding out her favorite day of the week can tell you a lot about her personality.

5. What’s the most you’ve ever had to drink in a single night?

There are unwritten rules governing the use of alcohol, and drinking in general is seen as a masculine activity.

Although the discussion may veer in that direction, this question is really meant to gauge how much of a lightweight or heavyweight drinker she is. An embarrassing but funny story might ensue.

6. Would you rather be trapped in a dark small box or at a Justin Bieber concert with no doors or windows?

One of the most random questions to ask a girl, but one that must be asked.

The pop star has insane fans, and even more insane enemies. Granted it’s mostly guys who detest him for his effeminate and cheesy ways, a surprisingly large number of girls do as well. What does she think about Justin Beiber?

7. What do you think of girls proposing to guys?

“The way proposals work is too messed up. Why must only one person deal with the pressure? Why is the guy usually the one deemed wise enough to know the right time to propose?”

Just a few things she might wonder. Marriage is a very touchy subject for both men and women, but one worthy of discussion.

8. Are you a snorer?

This is one of the most embarrassing questions to ask a girl. Snoring is not just a guy thing like conventional wisdom would have you believe. Girls snore, too, but this is hardly something they like to advertise.

She might blush out of discomfort, but ask anyway. It will spice things up.

9. What’s the last lie you told?

People are dirty liars. Did you know that the average person tells upwards of 200 lies every day? It’s true!

In other words, she would be the biggest liar on earth if she tells you she doesn’t lie. In fact, it would be such an egregious and audacious lie that you would be better off not being involved with her.


10. Do you have a “phone voice”?

Many girls sound s**ier on the phone than they look in real life. There, I said it, so shoot me!

Care to find out if she’s one of those girls? Does she even have a phone voice? Heck, take out your cells and start a phone conversation on the spot if you’re both so inclined.

11. Have you ever dropped money, noticed, and just kept on walking?

It’s one thing for you to find someone else’s dropped money then wrestle with the ethics of keeping it, but it’s an entirely different thing for you to realize that you’ve dropped your own money and then ignore it.

If she answers “No”, she’s ‘normal; if she answers “Yes”, there might be something “unique” about the way she thinks and her relationship with money that you need to know

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