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When you first meet a new guy, asking him lots of interesting questions will help you get to know him better and find out whether he’s right for you.
But even if you’ve been with a guy for years, you can always learn new things about him by asking personal, romantic, and deep questions. It’s a great way to keep your relationship fresh and strengthen your emotional connection.
Whatever stage your relationship is at, asking these questions will give you a better understanding of your guy and what makes him tick.
Ice breaker questions to get to know your crush
These questions are perfect if you’re trying to get to know a guy on a date or at a party. They’ll help you break the ice and get him talking so you can learn more about him.
- Where were you born?
- Do you have any brothers or sisters?
- What do your parents do for work?
- Do you have a good relationship with your family?
- Do you enjoy your job right now?
- Where do you see yourself in 5 years?
- What do you do for fun?
- What’s your favorite musical genre?
- What’s your favorite movie and TV show?
- Do you play any sports?
- Do you have any pets?
- What kind of books do you like to read?
- What is your dream job if money was no object?
- How would your friends describe you?
- What goals do you most want to achieve in your life?
- Would you rather live in the city, the suburbs or out in the country?
- Are most of your friends still single or do they have partners?
- What’s the most important quality you look for in a girlfriend or wife?
- Would you rather go out and party or stay in on Saturday night?
- Would you rather a small group of close friends or a larger group?
- Are you looking for commitment or casual fun?
- Do you like to plan everything out or just go with the flow?
- What’s something about yourself that you’ve never told anyone?
Personal questions to ask a guy
To really get to know someone, you need to probe a little deeper, and these personal questions to ask a guy help you do just that. You can learn about his hopes, dreams, and passions while also getting a better understanding of the way he sees the world.
- What personal achievement makes you most proud?
- What are you most thankful for in your life?
- Do you want to have kids someday?
- What was your last relationship like and how did it end?
- Who do you most admire and why?
- What is the most important aspect of life for you?
- What do you think makes a successful relationship?
- What’s the biggest lesson you’ve learned from your past relationships?
- If you could change one thing about your life, what would it be?
- What are your deal breakers in a relationship?
- What decision do you regret most in your life?
- Who has influenced you the most?
- What’s the most terrifying thing you’ve ever done?
- What do you feel most insecure about?
- What family traditions are important to you?
- What’s the most important thing you’ve learned from your parents?
- When was the last time you cried?
- What’s the most daring thing you’ve ever done?
- What’s the most romantic thing you’ve ever done for someone?
- What do you think is the key to a happy and lasting relationship?
- What’s the most difficult decision you’ve ever had to make?
- Have you ever had your heart broken?
- When have you felt the most alone in your life?
- If you could reset your life and try it again, would you?
- Are you hopeful or pessimistic about the future?
- What aspects of your childhood would you most want your children to experience?
- What quality do you most love about yourself?
- Are there any causes you would die for?
- What are you most afraid of?
- Have you ever been in trouble with the law?
- What do you hate the most in life?
- Is there anything you’ve done that you can never forgive yourself for?
- What do you look forward to the most each year?
- What’s the best and worst advice you’ve ever received?
- If you could take back one thing you said, what would it be?
- What made you laugh harder than anything else this year?
- How long do you usually date a girl before you go exclusive?
- What career would you advise your children to pursue?
- Have you ever been in a fight and why did it start?
- Has anyone you know suffered from addiction?
- How would you describe your political views?
Deep questions to ask your boyfriend
If your guy seems like a more serious and reflective type, these thought provoking questions will really get him thinking. Use them to explore his views on everything from religion and ethics to the meaning of life.
- Do you believe in second chances?
- If you had 24 hours left to live, what would you do?
- Do you think people are truly capable of change?
- Do you believe in reincarnation?
- What do you think happens to us after we die?
- If you could ask one question to God, what would it be?
- Do you think humans are essentially good or evil?
- Do you think humanity has any hope of surviving?
- Do you think people should take more risks or play it safe?
- What do you think happens to us when we die?
- Do you think extraterrestrial life exists?
- What do you think is the most important thing we need to learn in this lifetime?
- Do you think people are truly capable of change?
- What do you think is the meaning and purpose of life?
- Do you think we control our own destiny or is it predetermined?
- Is it more important to be liked or respected?
- If you could choose immortality, would you?
- Have you ever felt like giving up on life?
- What’s the closest you’ve ever come to dying?
- What do you think is the most important thing to focus on in life?
- How long do you think people will remember you after you die?
- How many people do you think would attend your funeral?
- What message would you write on your own tombstone?
- Has anyone you were close to died?
- What would someone have to do to deserve the death penalty?
- Are you afraid of dying?
- What do you think is the most important lesson we can learn in life?
- How do you define happiness, and what are your tips for achieving it?
- How do you define success, and what are your tips for achieving it?
- What do you think is the key to a lasting and fulfilling relationship?
- Do you think humans will eventually live forever?
- Is there anything you’re afraid of dying before doing?
- What do you think is the most important thing to focus on in life?
- Do you think money can buy happiness?
- How much control does a person have over their life?
- Why are the dead respected more than the living?
- If you could make a perfect copy of yourself, would it be you?
- If humans have a soul, where is it located?
- Is it better to have deep knowledge of a few things or a little knowledge of a lot of things?
- If humans believe in different Gods, how can they all be true?
- Do you think humans have free will?
- Is it okay to do something wrong if no one ever knows you did it?
- Is it more valuable to be intelligent or wise?
- How do you think the human race will eventually go extinct?
- Do you think we are living in a computer simulation?
- Can a person be happy if they don’t have any goals in life?
- What do you think is the meaning of life?
- Do you believe in soulmates or true love?
Fun questions to ask a date
Try asking a guy these lighthearted and fun questions to get to know him a little better. Even though many of these questions will make him laugh, you can still learn a lot about his interests and values by reading between the lines.
- What’s the weirdest question you’ve ever asked Google?
- Who would you most like to be stranded on a desert island with?
- What’s the stupidest thing you’ve ever bought?
- What’s the first thing you would buy if you won the lottery?
- What celebrity would you most like to go on a date with?
- If you could have 3 wishes, what would they be?
- What animal would you most like to be?
- What’s the dumbest thing you believed as a child?
- If you could only watch one movie for the rest of your life, what would you choose?
- If someone has food on their face, do you tell them or ignore it?
- What name would you give your new boat?
- What actor should play you in the movie about your life?
- If you could have a superpower, what would you choose?
- What talent do you have that not many people know about?
- If you could only wear one outfit for the rest of your life, what would you pick?
- Would you rather be an angel or a devil?
- Do you prefer to get up late or stay up late?
- Would you rather be rich and famous, or rich and anonymous?
- Are you a cat person or a dog person?
- What would you choose for your last meal on earth?
- What’s something you do that makes you feel old?
- Who would you choose to narrate the audiobook of your life?
- If magic was real, what spell would you learn first?
- Would you rather be too hot or too cold?
- Do you eat food past the expiry date if it passes the smell test?
- What app needs to exist but doesn’t?
- What was the last lie you told?
- What’s the worst hairstyle you’ve ever had?
- What’s the worst name you could give a child?
- What’s the most awkward situation you’ve ever been in?
- Have you ever had a dream about a celebrity?
- What would be your dream vacation spot?
- If you could own any pet, what would it be?
- Do you like adventures or do you prefer to stay in your comfort zone?
- What’s the most daring thing you’ve ever done?
- Do you like challenges or do you prefer things to be easy?
- What’s the best prank you’ve ever pulled?
- Have you ever had a crush on a teacher or authority figure?
- What’s the most embarrassing thing that’s ever happened to you?
- What’s the funniest pick up line you’ve ever heard?
- What’s the worst pick up line you’ve ever heard?
- Have you ever been in a situation where you had to fake being sick?
- What’s the most daring thing you would do on a first date?
- What’s the worst first date you’ve ever been on?
- Do you like surprises or do you prefer to know what’s going on?
- What’s the funniest prank you’ve ever played on someone?
- What’s the best April Fool’s Day prank you’ve ever seen?
- Have you ever played a prank that backfired?
- What’s the most embarrassing thing that’s happened to you in public?
- Do you have any phobias?
- What’s the worst injury you’ve ever had?
- What’s the best/worst piece of advice you’ve ever been given?
- Who’s your celebrity crush?
- What’s the most interesting place you’ve ever visited?
- What’s the worst gift you’ve ever received?
- Do you have any quirky habits?
- What items are on your bucket list?
- What’s the worst fashion trend you’ve bought into?
- What is the worst movie you’ve ever seen?
- What’s the best catchphrase you’ve ever heard?
- What would you do if you could be invisible for a day?
- What’s the worst thing you’ve gotten away with?
- What was your favorite childhood candy?
- How would you describe yourself in three words?
- What’s the funniest meme you’ve seen?
- What’s your favorite TV show theme song?
- Who’s your favorite cartoon character?
- What was your favorite toy as a kid?
- Do you believe in ghosts and have you ever seen one?
- What’s the best Halloween costume you’ve ever seen?
- What’s the funniest joke you’ve ever heard?
- What’s the most interesting place you’ve ever visited?
- What’s the worst gift you’ve ever received?
- Do you have any quirky habits?
- What’s the weirdest thing you’ve ever eaten?
- If you met an alien, what is the first question you’d ask it?
- If you could live in any tv or movie universe, what would you choose?
- What’s the most difficult thing you know how to do?
- Have you ever seen a UFO?
- If you could travel to any time period, which one would you choose?
- Have you ever had a dream that came true?
- Would you go to space if you had the chance?
- Do you prefer summer or winter and why?
Flirty questions to ask a guy
Flirting is a great way to show a guy you like him without coming on too strong. Some women are naturally good at flirting and seem to have every guy eating out of the palm of their hand. But for most girls (and guys), it’s a skill that you need to practice. These romantic & flirty questions are perfect for getting a guy to take notice of you and start flirting back.
- Do you think I’m naughty or nice?
- What nickname would you give me?
- Would you get jealous if you saw me talking to another guy?
- Tell me something about yourself that no one else knows
- Would you prefer a girl to be good in the kitchen or the bedroom?
- What outfit do you think I’d look sexiest in?
- How would you describe me to your friends?
- Do you believe in love at first sight?
- What celebrity do I remind you of the most?
- How old were you when you first kissed a girl?
- What do you think is my most attractive feature?
- If we had kids, what physical feature would you like them to get from each of us?
- What was your first impression of me when you saw me?
- What’s the craziest thing you’ve ever done to impress a girl?
- Do you like it when girls make the first move?
- What turns you on the most about a girl you just met?
- What’s your perfect date?
- If you never saw me again, what would you miss the most?
- What was your first time like?
- Do you think I’m cuter or more sexy?
- What animal do I most remind you of?
- What type of lingerie would you like me to wear for you?
- Are you more into butts or boobs?
- Have you ever had a dream about me?
- What’s the sweetest thing I’ve ever done for you?
- How would you describe our relationship?
- Do you like it when I text you randomly or do you prefer that I wait for you to text me first?
- What do you think about public displays of affection?
- When was the first time you held a girls hand?
- Have you ever written a love letter to a girl?
- If you saw a shooting star, what would you wish for?
- How many dates do you usually wait before you try and sleep with a girl?
- What do you like most about our relationship?
- Do you have any weird fetishes?
- Do you think we have a future together?
- What do you like most about me?
Dirty questions to ask your crush
If you connect strongly with a guy, hopefully things get romantic before too long. These more hardcore dirty questions will get him to open up and share his sexy side.
- What’s your favorite sexual fantasy?
- Do you like it when a girl talks dirty to you?
- Have you ever had sex in a public place?
- Does watching porn with a girl turn you on?
- Do you prefer sex in the morning or at night?
- Do you prefer slow and sensual sex or hard and rough sex?
- Would you rather be dominant or submissive?
- What’s your favorite sex position?
- Have you ever sent a nude pic to a girl?
- What’s the filthiest thing you’ve ever tried in bed?
- What’s the hottest sex dream you’ve ever had?
- What’s your favorite part of the female body?
- What is the most amount of times you’ve ever had sex in one day?
- Have you ever bought a girl lingerie?
- What is the best thing a girl can do for you in bed?
- Have you ever had sex in a spa or swimming pool?
- Have you ever had a friend with benefits?
- Have you ever been to a strip club?
- How long do you think you could last without having sex?
- Where is your favorite place to kiss a girl?
