760 Questions to Ask a Guy

Want to get to know a guy better but not sure where to start? Don’t worry, you’re not alone!

Asking questions is like unlocking a treasure chest of someone’s personality. From dreams and hobbies to those quirky little details, the right questions can help you discover the real him.

Over Text

What’s your all-time favorite movie?
Do you prefer the beach or the mountains?
What’s the last book you read that you really liked?
Are you a morning person or a night owl?
What’s your dream job?
Do you like to cook? If so, what’s your go-to dish?
How do you usually unwind after a long day?
What’s your favorite type of music?
Are you into sports? Which ones?
What’s a place you’ve always wanted to visit?
Do you have any hidden talents?
What’s something you’re really passionate about?
How do you like to spend your weekends?
Are you a coffee person or a tea person?
What’s the most interesting thing that happened to you this week?
What’s your favorite childhood memory?
Do you like pets? Do you have any?
What’s your favorite kind of food?
If you could meet any famous person, dead or alive, who would it be?
What’s a hobby you’ve always wanted to pick up but never did?
Do you believe in ghosts or the supernatural?
What’s your favorite way to exercise?
Are you a fan of rollercoasters?
What’s something you’re really good at?
Do you have any favorite TV shows right now?
What was the last concert or live event you went to?
Do you like to dance?
What’s your go-to joke or funny story?
What’s something you wish you were better at?
If you could go back in time for one day, when and where would you go?

To Ask a Guy You Like

What’s the most adventurous thing you’ve ever done?
What are your top 3 favorite foods?
What’s a movie that made you cry?
Do you have any siblings? Are you close with them?
What’s the best piece of advice you’ve ever received?
What’s the first thing you’d do if you won the lottery?
What’s your idea of a perfect date?
Are you a romantic person?
What’s your zodiac sign? Do you believe in astrology?
What’s the most important quality you look for in a partner?
What’s your favorite season and why?
If you could only eat one thing for the rest of your life, what would it be?
Do you like spicy food?
What’s your favorite way to celebrate your birthday?
Do you enjoy going to parties?
What’s the most recent show you binge-watched and loved?
What’s your opinion on pineapple on pizza?
Are you an indoor or outdoor person?
Do you play any instruments?
What’s your favorite type of candy?
What’s a skill you wish you had?
Do you like going to the movies or prefer watching at home?
What’s your favorite animal?
Do you have a favorite quote or saying?
Do you believe in love at first sight?
What’s a place you feel most at peace at?
What’s your favorite board game or card game?
Are you competitive?
What’s your favorite way to spend a rainy day?
What’s something you’re afraid of?
Do you like to travel alone or with people?
What’s your favorite type of flower?
Are you a good swimmer?
What’s a language you’d love to learn?
What’s your favorite type of cake?
What kind of music makes you want to dance?
Do you like watching sports live or on TV?
Do you have any cool scars with stories behind them?
What’s your spirit animal?
Do you believe in karma?
What’s your favorite thing about yourself?
What’s your go-to comfort food?
What’s a job you would never want to do?
Do you like tattoos? Do you have any?
What’s the most valuable lesson you’ve learned so far?
What’s a cause you feel strongly about?
What’s your favorite kind of ice cream?
Are you a planner or more spontaneous?
What’s your favorite thing to do on a Sunday morning?
What’s a tradition you have with your friends or family that you love?

To Ask a Guy Friend

What’s the weirdest food you’ve ever tried?
What’s the best vacation you’ve ever been on?
How do you feel about roller skating?
If you had a time machine, would you go to the past or the future?
What’s your favorite thing about our friendship?
Do you have a favorite video game?
What’s the most challenging thing you’ve ever done?
Are you good at keeping secrets?
Have you ever pulled a prank on someone?
What’s your dream car?
Do you believe in aliens?
What’s your favorite kind of soda?
How many countries have you been to?
What’s your go-to karaoke song?
Do you collect anything?
What’s your favorite subject in school (or what was it)?
What’s a skill you’d like to master?
Do you enjoy hiking?
Are you a clean or messy person?
What’s your favorite social media platform?
Do you like camping?
What’s the best concert you’ve ever been to?
Do you believe in soulmates?
What’s the first thing you’d do in a zombie apocalypse?
Do you like solving puzzles?
What’s the best gift you’ve ever received?
What’s your favorite childhood toy?
What’s a food you absolutely hate?
What’s the funniest thing you’ve ever witnessed?
Have you ever met anyone famous?
What’s a movie or show that you think is overrated?
What’s your favorite type of weather?
What’s your favorite sport to watch?
Do you enjoy going to museums?
What’s your favorite holiday?
Do you like to sing in the shower?
What’s a childhood game you loved?
Do you have a favorite comedian?
What’s your go-to snack at a movie theater?
Have you ever won anything? What was it?
Do you like DIY projects?
Are you a good dancer?
What’s the last photo you took on your phone?
Do you like to people-watch?
What’s your favorite way to exercise?
What’s your least favorite chore?
Do you like horror movies?
What’s the most beautiful place you’ve ever seen?
What’s your favorite type of sandwich?
What’s a talent you have that not many people know about?

To Ask a Guy Before Dating

What are you looking for in a relationship?
Do you want to have kids in the future?
What are your views on marriage?
How do you handle stress or disagreements?
What are your career goals?
Do you have any deal-breakers in a relationship?
How important is religion or spirituality to you?
What’s your love language? (Words of affirmation, physical touch, etc.)
How do you feel about long-distance relationships?
What’s your view on finances in a relationship?
How often do you like to communicate with your partner?
What are your thoughts on gender roles?
How important is family to you?
Are you open to counseling or therapy if needed?
What’s your attitude towards health and fitness?
How do you spend your free time?
How do you feel about pets?
Do you smoke or drink? Are you okay with a partner who does?
What’s your social life like?
What’s your favorite way to show affection?
What’s the best relationship you’ve ever been in, and why did it end?
Do you have any food allergies or dietary restrictions?
What’s your opinion on moving in together before marriage?
How do you feel about public displays of affection?
Do you have any relationship deal-makers?
What are your political views?
How do you feel about monogamy?
How do you handle conflict in a relationship?
Do you have a close relationship with your family?
What do you think is the key to a successful relationship?
How do you feel about sharing chores?
What’s your ideal date night?
How would you describe your sense of humor?
Do you have any goals for the next five years?
What are your thoughts on social media and relationships?
How do you like to celebrate anniversaries?
What are your favorite and least favorite things about dating?
Do you have any travel goals or places you want to visit?
How do you feel about jealousy in a relationship?
What’s your take on friendships with the opposite sex while in a relationship?
How do you feel about celebrating holidays?
What’s your stance on open relationships?
What qualities do you admire in a partner?
How do you feel about discussing past relationships?
What’s the one thing you’d like to accomplish in the next year?
Do you consider yourself an introvert or an extrovert?
How do you handle work-life balance?
What are your views on mental health?
What’s your attitude toward cheating in relationships?
Are there any topics you consider “off-limits” for discussion?

To Ask a Guy You Just Met

What do you do for work?
Where are you from originally?
How do you usually spend your weekends?
What kind of music are you into?
Are you more of a city or country person?
Do you have any favorite restaurants around here?
What’s your favorite thing to do in this town?
Are you into any TV shows right now?
What’s the last movie you watched?
Do you have a go-to coffee shop?
What’s your favorite type of cuisine?
Do you like to read? What’s your favorite book?
What kind of sports are you into?
Are you a fan of podcasts? Any favorites?
What’s your favorite way to stay active?
What’s your go-to drink when you’re out?
Are you a fan of art? Do you like to visit galleries?
Do you like to travel? What’s your dream destination?
Are you a student? What are you studying?
What’s your favorite type of comedy?
Are you good at trivia?
Do you enjoy cooking or baking?
Are you a summer or winter person?
Do you have a favorite type of dessert?
Do you have any cool plans for the rest of the week?
What’s the most fun event you’ve been to recently?
Do you like doing things outdoors?
Are you into technology and gadgets?
How do you get your news?
What’s your favorite kind of breakfast?
Do you enjoy board games or card games?
Do you like to go fishing or camping?
What’s a talent you wish you had?
What’s the craziest thing you’ve done on a dare?
Do you like going to music festivals?
Are you into photography?
Do you like going to the gym?
What’s your favorite way to relax after a busy day?
Are you an early bird or a night owl?
Do you like mystery or suspense movies?
Are you into any kinds of crafts or DIY?
Do you like going to the theater or watching plays?
What’s a skill you’re really proud of?
Do you have any favorite YouTube channels?
What’s a place nearby that you’ve always wanted to visit but haven’t yet?
Do you like rollercoasters and theme parks?
Are you a thrill-seeker?
What’s your favorite comfort food?
Do you have any funny habits?
What’s something you’ve always wanted to try but haven’t yet?

To Ask a Guy Before Marriage

How do you envision our life together in 10 years?
What are your expectations for married life?
How important is it for you to have a religious or spiritual wedding?
What’s your approach to handling money and finances as a couple?
What are your thoughts on prenuptial agreements?
How would we handle disagreements or conflicts in our marriage?
How often do you think married couples should be intimate?
What’s your view on spending time with in-laws?
How involved would you want to be in planning our wedding?
Do you see yourself as the primary breadwinner?
How would we decide where to live?
How do you feel about adopting children if we can’t have our own?
Would you be open to marriage counseling if we hit a rough patch?
What’s your opinion on couples having separate bank accounts?
How would we handle it if one of us got a job opportunity in a different city or country?
What are your thoughts on parental roles and responsibilities?
How would we handle childcare? Would one of us be a stay-at-home parent?
How do you feel about taking joint family vacations?
What are your expectations for holidays and traditions?
What’s your stance on privacy within a marriage?
How would you like to handle chores and household duties?
What are your thoughts on family planning and contraception?
Do you believe in setting relationship goals?
How would we deal with interference from extended family members?
How important are anniversaries to you?
How do you feel about each other’s friends?
What’s your approach to maintaining our individual identities in marriage?
How would we navigate issues around religion or spirituality?
How do you feel about supporting each other’s careers and ambitions?
How would you handle it if one of us faces a serious health issue?
How would we manage a long-term separation due to work or family commitments?
What are your thoughts on taking time off to travel or live abroad?
What are your opinions on gender equality within a marriage?
How do you handle stress, and what would you expect from me during stressful times?
How do you feel about giving each other personal space?
How would we make decisions about major life events or changes?
What’s your take on managing relationships with ex-partners?
How do you feel about supporting each other in hobbies and interests?
What are your thoughts on gift-giving in a marriage?
Would you be open to attending couples’ workshops or relationship courses?
How do you envision our day-to-day life after getting married?
How would you handle it if we face fertility issues?
What’s your philosophy on lending or borrowing money within the family?
How would we set priorities as a married couple?
How would you handle disagreements about political or social issues?
What are your expectations about name changes after marriage?
How would you feel about getting a pet?
How do you feel about surprise gestures or actions in a marriage?
What are your views on setting up a family budget?
What’s the most important value you’d want to uphold in our marriage?

Flirty Questions

What’s the first thing you noticed about me?
What do you think is my best feature?
How would you describe me in three words?
What’s your idea of a perfect date night?
What’s the most romantic thing you’ve ever done?
How do you feel about holding hands in public?
What’s your love language?
What’s your go-to pickup line?
Are you a hugger or a kisser?
What’s the best compliment you’ve ever received?
What’s the most adventurous date you can think of?
What do you wear when you want to impress someone?
Do you believe in love at first sight?
How would you make our first date unforgettable?
How would you describe your flirting style?
If you could plan a dream date, what would it be?
What’s a song that you think describes us?
Do you get jealous easily?
How do you know you’re really into someone?
What do you think is your most attractive quality?
Do you like it when the girl makes the first move?
What’s the most romantic movie you’ve ever seen?
What’s a secret talent you have that not many people know about?
What would you do if I kissed you right now?
Do you like to dance? Would you dance with me?
How would you react if I told you that you’re cute?
Do you like playful or serious conversations more?
What’s the most daring thing you’ve done in love?
Do you prefer to text or call?
What’s a deal-breaker for you in a relationship?
What’s the best way to win you over?
How do you feel about pet names like “honey” and “babe“?
What’s a romantic gesture that you think is underrated?
Do you have a “type“?
How do you feel about public displays of affection?
What’s the best way to get your attention?
Do you have any romantic fantasies?
How would you charm someone you’re really into?
What’s a place you think is super romantic?
What’s the most flirty emoji, in your opinion?
How would you sweep me off my feet?
What’s the sweetest thing you’ve done for someone you liked?
What’s your favorite love quote or lyric?
What’s the most romantic place you’ve ever been to?
How do you like to spoil someone you’re into?
Do you like to cuddle?
How would you react if I said I find you attractive?
What’s a good excuse for us to get closer?
What do you find irresistible in a person?
How would you feel if I asked you out?

Random Questions

What’s the last book you read?
If you could travel back in time, what era would you visit?
What’s your favorite meal of the day: breakfast, lunch, or dinner?
If you could have dinner with any three people (dead or alive), who would they be?
What’s your go-to karaoke song?
Do you believe in aliens?
What’s your spirit animal?
What’s a skill you’ve always wanted to learn?
If you were a superhero, what would your powers be?
What’s the best concert you’ve ever been to?
Do you have any hidden talents?
What’s your favorite type of weather?
If you could be famous for one thing, what would it be?
What’s a movie you can watch over and over again?
What’s the most daring thing you’ve ever done?
Are you a morning person or a night owl?
What’s your favorite board game?
What’s your dream job?
If you could live in any fictional world, where would it be?
What’s the best gift you’ve ever received?
What’s your biggest pet peeve?
What’s your favorite kind of exercise?
Do you like to cook? If so, what’s your best dish?
What’s your favorite way to relax after a long day?
What’s something that always makes you laugh?
What’s your favorite family tradition?
If you could have any car in the world, what would it be?
Do you have a favorite quote or saying?
What’s the most beautiful place you’ve ever been to?
What’s your idea of a perfect weekend?

Weird Questions

If you could have any mythical creature as a pet, what would you choose?
What’s the strangest food you’ve ever tried and liked?
Would you rather fight one horse-sized duck or a hundred duck-sized horses?
What’s the weirdest dream you’ve ever had?
If you could be invisible for a day, what would you do?
What’s a weird habit you have that not many people know about?
If you could switch lives with a cartoon character, who would it be?
What’s the weirdest smell you actually like?
If you had to eat only one color of food for a week, what color would it be?
What’s the most useless talent you have?
If you could only speak in movie quotes, what movie would you choose?
What’s the weirdest thing you’ve ever Googled?
If your life was a movie, what would the title be?
What’s the strangest place you’ve ever visited?
If you could have dinner with any fictional character, who would it be?
What’s the most bizarre thing you’ve ever found attractive in someone?
Would you rather have fingers as long as your legs or legs as long as your fingers?
What’s the weirdest thing you’ve ever done on a dare?
If you could be any vegetable, what would you be?
What’s the strangest song you’ve ever heard but enjoyed?
Would you rather never have to sneeze again or never have to hiccup again?
What’s the weirdest thing you’ve ever found on the street?
If you could smell like one food for the rest of your life, what would it be?
What’s the most bizarre thing you’ve ever done to impress someone?
If you could have a useless superpower, what would it be?
What’s the weirdest thing you’ve ever seen in someone else’s home?
What’s the oddest thing you’re afraid of?
What’s the weirdest way you’ve ever made a friend?
If you could instantly learn one dance move, what would it be?
What’s the strangest thing you’ve ever found appealing?

Funny Questions

If you were a vegetable, what would you be and why?
What’s the weirdest nickname you’ve ever had?
If animals could talk, which one do you think would be the most annoying?
What’s the most ridiculous fact you know?
If you were a wrestler, what would your entrance theme song be?
What’s the silliest reason you’ve ever gotten into trouble?
If you had to replace your hands with something else, what would you choose?
What’s your go-to dance move?
What would be the title of your autobiography?
What’s the most useless piece of knowledge you have?
If you could have an endless supply of food, what would you pick?
What’s the worst haircut you’ve ever had?
What’s your most embarrassing childhood memory?
What’s the weirdest talent you have?
What’s the worst joke, you know?
What’s the most absurd thing you’ve ever heard someone say?
What would your supervillain name be?
If you could only speak in rhymes, how would you introduce yourself?
What’s the most ridiculous outfit you’ve ever worn?
What would you do if you were the last person on Earth?
If you were a kitchen appliance, what would you be?
What’s the funniest word you can think of?
If you could be any character in a comedy movie, who would you be?
What’s the funniest prank you’ve ever played on someone?
If you had to eat a crayon, what color would you choose?
What’s the most embarrassing song you know all the lyrics to?
If you could instantly become an expert in something, what would it be?
What’s the funniest thing you’ve ever heard a child say?
What’s the worst piece of advice you’ve ever received?
What’s the most hilarious animal video you’ve ever seen?

Romantic Questions

How did you know you were falling for me?
What makes you feel most loved?
What’s your idea of a perfect kiss?
How do you imagine our future together?
What was your first impression of me?
What’s the most romantic date you can think of?
What’s your favorite thing about our relationship?
What’s your favorite way to show affection?
How do you feel about long-term commitments?
What’s the most meaningful gift you’ve ever received from a partner?
How do you handle disagreements in a relationship?
What qualities are most important to you in a partner?
How do you like to celebrate anniversaries?
What’s the most romantic book you’ve ever read?
Do you believe in soulmates?
What’s a love story that inspires you?
What’s the most romantic gesture you’ve ever received?
How would you describe your ideal home with your future partner?
What’s a moment you knew you were in love?
How do you want to be proposed to, or how would you propose?
How do you like to make up after an argument?
What’s the most romantic vacation you can plan?
What’s your favorite memory with me?
What does romance mean to you?
How do you like to be comforted when you’re sad?
What’s your favorite romantic quote?
What’s your go-to love song?
What’s the most romantic thing you want to do someday?
How would you spend a romantic weekend indoors?
Do you like sentimental gifts or practical gifts?
What’s the first thing that caught your eye about me?
How do you define love?
How would you feel about writing love letters to each other?
What’s a romantic movie you’d like to watch together?
Do you like sunrise or sunset dates?
How do you know when you’re deeply connected with someone?
How would you make a long-distance relationship work?
What’s the most important lesson you’ve learned from past relationships?
Do you enjoy stargazing?
What’s the most romantic restaurant you know?
What’s the best way to express love besides saying “I love you“?
How do you handle stress in a relationship?
What’s your favorite couple’s activity?
How would you spend your ideal Valentine’s Day?
How do you feel about relationship milestones like moving in together?
What’s a romantic tradition you’d like to start?
What’s the most romantic thing you’ve ever done for someone?
What’s the most romantic scene from a movie or show that you love?
How do you keep the spark alive in a relationship?
What’s something romantic that you’ve always wanted to do?

About Relationships

How long was your longest relationship?
What do you think is the most romantic thing you can do for someone?
Do you think it’s okay to keep secrets in a relationship?
How do you feel about public proposals?
What’s your idea of the perfect honeymoon?
How do you know when you’re in love?
Do you think it’s possible to stay friends with an ex?
What’s the biggest relationship mistake you think people make?
What’s more important: physical attraction or emotional connection?
Do you believe in “the one“?
How do you feel about couples sharing passwords?
What’s your opinion on work-life balance when in a relationship?
Do you think couples should have a joint bank account?
How important is it to meet your partner’s family?
How would you handle disagreements in a relationship?
Do you think a relationship can recover from cheating?
What are your thoughts on age differences in a relationship?
How do you feel about dating someone from a different cultural background?
Do you think it’s important for a couple to share hobbies?
How would you feel about relocating for love?
What’s your opinion on long-term relationships without marriage?
How do you feel about couples counseling?
Do you think it’s important to celebrate monthly anniversaries?
What’s your stance on dating apps and websites?
How important is your partner’s career to you?
What’s your opinion on couple’s vacations?
How soon do you think it’s okay to say “I love you“?
What are your views on “taking a break” in a relationship?
How do you feel about lending money to your partner?
Do you think opposites attract?
What’s your view on dating someone with kids?
How important is it for you to get your family’s approval of your partner?
How do you feel about spending holidays with a partner’s family?
Do you believe that every relationship should have a “leader“?
What’s your opinion on pet names for partners?
How do you feel about sharing household responsibilities?
What’s the most important holiday for couples to celebrate together?
What are your thoughts on giving and receiving expensive gifts?
Do you think it’s important for both partners to cook?
How do you feel about your partner having close friends of the opposite sex?
What’s your view on having a “date night” regularly?
What are your thoughts on social media PDA (Public Display of Affection)?
What’s the most romantic destination you can think of?
How do you feel about couples who work together?
What are your thoughts on having separate bedrooms?
Do you believe in relationship “rules“?
What’s your opinion on celebrating “half-anniversaries“?
How do you feel about going on double dates with other couples?
What are your thoughts on renewing wedding vows?
How do you feel about couples having a song, movie, or place that’s “theirs“?

About His Hobbies and Interests

What’s your favorite way to unwind after a busy week?
Do you play any musical instruments?
What’s a hobby you’ve always wanted to pick up but never did?
What kind of movies do you like to watch?
Are you into sports? If so, which ones?
Do you like to go fishing or camping?
What’s the most challenging thing you’ve ever built or made by hand?
Are you into video games? What’s your favorite?
Do you have a go-to workout or exercise routine?
What’s your favorite type of music?
Have you ever been in a band or performed on stage?
Do you enjoy cooking? What’s your signature dish?
Do you like to draw or paint?
What’s your favorite podcast?
Are you a fan of any TV series right now?
What was the last event or concert you went to?
Do you enjoy hiking or outdoor adventures?
Do you have a favorite author or book genre?
Are you into photography?
What’s a movie or show you could watch over and over?
Do you have any favorite YouTubers or streamers?
Do you enjoy gardening?
Do you like to dance?
What’s a sport you’ve always wanted to try?
Do you have a favorite board game or card game?
Are you into any extreme sports like skydiving or surfing?
What’s the coolest craft you’ve ever done?
Are you a fan of any specific sports teams?
What’s your favorite way to stay active?
Do you like traveling? Where’s the last place you visited?
Do you enjoy doing puzzles or brain teasers?
What’s your favorite museum or art gallery?
Are you into astronomy?
Do you collect anything?
What’s your favorite type of food to cook or bake?
Do you enjoy DIY projects?
Are you a fan of any specific video game series?
Do you like to write, maybe stories or a journal?
What’s your go-to social activity?
Do you have any favorite magazines or blogs you read regularly?

About His Family and Friends

How many siblings do you have, and what are they like?
Are you close with your parents?
Do you have any family traditions that are special to you?
What’s the best advice a family member has given you?
How often do you get together with your family?
Do you have a favorite family vacation memory?
Who in your family are you most similar to?
What’s your favorite thing to do when you visit your hometown?
What’s a typical family gathering like for you?
Are there any family recipes that you love?
How do you celebrate major holidays with your family?
Do you have any nieces or nephews?
What’s the most important lesson your family has taught you?
Do you have any family members you consider as role models?
What’s a funny family story that always gets brought up?
Who’s your oldest friend, and how did you meet?
How do you usually spend time with your friends?
Do you have a best friend? How did you two meet?
What’s the most adventurous thing you’ve done with friends?
Do you and your friends have any inside jokes?
What qualities do you value most in a friendship?
How do you handle disagreements with friends?
What’s the most memorable trip you’ve taken with friends?
Do your friends and family ever hang out together?
How do your friends describe you?
Are there any friendships you regret losing?
Do you have a group of friends you usually hang out with?
How often do you catch up with old friends?
What’s the best gift a friend has ever given you?
Do your friends ever embarrass you? How?
What’s a tradition you have with your friends?
Do you like introducing your friends to each other?
How do you support your friends when they’re going through tough times?
Have you ever lived with a friend? How was it?
Are you friends with any of your coworkers or classmates?
Do you have any friends you’ve known since childhood?
How do you make new friends?
What’s the most important thing you’ve learned from your friends?
Do you have any friendships that started in a unique or funny way?
Are there friends or family you wish you were closer to?

About Travel and Adventure

What’s the most exciting place you’ve ever visited?
Do you prefer traveling solo or with a group?
What’s your dream travel destination?
Do you like road trips? What’s the best one you’ve been on?
What’s the most adventurous thing you’ve ever done?
Have you ever been camping? How was it?
Are you into extreme sports like skydiving or bungee jumping?
What’s the most beautiful beach you’ve been to?
Do you like to travel for relaxation or adventure?
What’s your favorite type of vacation: beach, mountain, city, or countryside?
What’s your go-to travel snack?
How do you pass the time on long flights or drives?
Do you have a travel bucket list? What’s at the top?
What’s the most interesting local dish you’ve tried while traveling?
Have you ever traveled abroad? Where did you go?
What’s your favorite travel memory?
What are some travel essentials you can’t live without?
How do you pick where to go on vacation?
Have you ever gone on a spontaneous trip?
What’s the most challenging travel experience you’ve had?
Do you enjoy hiking? What’s the best trail you’ve ever hiked?
What’s the most beautiful natural wonder you’ve seen?
Do you like to visit museums and cultural spots when you travel?
Have you ever been on a cruise?
What’s the most remote place you’ve visited?
Do you prefer hotels, hostels, or Airbnb?
Have you ever traveled for a festival or special event?
Do you like to plan out your trips or just go with the flow?
What’s the next place on your travel list?
Have you ever been lost while traveling? What happened?
Do you prefer warm or cold travel destinations?
What’s the longest trip you’ve ever taken?
Have you ever taken a scenic train journey?
What’s your favorite way to document your travels?
Have you ever had a local show you around when traveling?
Do you like visiting tourist spots or hidden gems?
What’s the most interesting souvenir you’ve brought back from a trip?
Have you ever taken a cooking class in another country?
What’s your favorite travel app or tool?
Do you like to travel for work or just for fun?

About His Job and Career Goals

What do you do for a living?
Do you enjoy your job? Why or why not?
What’s your dream job?
How did you get into your current field?
What’s a typical workday like for you?
Have you ever thought about changing careers?
What’s the most rewarding part of your job?
Do you prefer working alone or with a team?
What’s the most challenging project you’ve worked on?
What are your career goals for the next five years?
Is there someone at work you really look up to?
How do you deal with work stress?
What’s your favorite part about your job?
Have you won any awards or gotten any promotions recently?
How do you balance work and personal life?
Do you like to bring your work home, or do you prefer to switch off after office hours?
What’s the best career advice you’ve ever received?
Do you have any side hustles or projects you’re working on?
What’s a skill you want to learn for your job?
Do you enjoy networking and meeting new people in your industry?
How do you stay updated on trends and news in your field?
Have you ever been to a professional conference or workshop?
Do you like to mentor others at work?
What would make you feel like you’ve “made it” in your career?
What’s the most important quality for someone to succeed in your field?
Do you plan on going back to school or getting more training?
What’s the first job you ever had?
Have you ever thought about starting your own business?
How do you handle criticism at work?
What’s a work-related book or course that has significantly helped you?
Do you work better under pressure or with plenty of time?
How do you prioritize tasks at work?
Do you set long-term career goals?
What’s your backup plan if things don’t work out in your current job?
Have you ever had to make a difficult decision at work? What did you do?
How do you get along with your boss and coworkers?
What’s the most useful piece of feedback you’ve gotten at work?
Is there a cause or mission that you feel passionate about in your job?
Do you prefer a structured work environment or a more laid-back setting?
Have you ever turned down a job offer? Why?

About Personal Growth and Dreams

What’s a personal goal you’re working on right now?
Do you have a “bucket list“? What’s in it?
What’s a book that changed your life?
Are there any habits you’re trying to build or break?
What’s a dream you’ve had since you were a kid?
How do you handle setbacks or failures?
What motivates you to get up in the morning?
What’s something you wish you were better at?
Have you ever faced a fear head-on? What happened?
What’s a risk you’re glad you took?
Do you have a mentor or someone you look up to?
What’s the best piece of advice you’ve ever received?
What’s something you’re proud of but don’t get to talk about often?
Do you have a personal motto or quote that inspires you?
How do you stay focused when you have a big goal ahead of you?
What’s a skill you want to learn just for fun?
What does “success” mean to you?
How do you deal with stress or burnout?
Are you a spiritual person? What practices or beliefs help you in life?
Do you like to volunteer or give back to the community?
How do you define happiness?
What’s a subject you wish you knew more about?
Do you have any creative outlets?
What’s the last thing that made you really excited?
Do you set New Year’s resolutions? Do you stick to them?
What’s a place where you feel completely at peace?
How do you push yourself out of your comfort zone?
What’s something you’re grateful for right now?
What’s the most impactful thing you’ve done for your personal growth?
What’s a goal you’ve achieved that you’re really proud of?
How do you approach self-care?
What’s a life lesson you had to learn the hard way?
How do you handle criticism or negative feedback?
What’s the biggest change you’ve made in your life so far?
Do you believe in destiny or that you create your own path?
What’s a dream job you’d pursue if money wasn’t an issue?
How do you recharge when you’re feeling drained?
Is there a cause or issue that you’re passionate about?
What’s the first thing you’d do if you won the lottery?
How do you want to be remembered?

About His Opinions and Beliefs

What’s a cause that really matters to you?
What’s your take on social media? Good, bad, or a mix of both?
Do you follow politics? What issues matter most to you?
How do you feel about climate change?
What’s your favorite genre of music and why?
Are you religious or spiritual? What are your beliefs?
Do you believe in life after death?
How do you feel about tattoos and piercings?
What’s your favorite movie and why?
Do you think money can buy happiness?
What’s your opinion on online dating?
Are you a dog person, a cat person, or neither?
How do you feel about long-distance relationships?
What are your views on marriage and divorce?
What’s a trend you just can’t get behind?
Do you believe in fate or free will?
How do you feel about gender roles in relationships?
What’s your opinion on fast food?
How do you feel about public speaking?
What’s your stance on privacy and sharing personal info online?
Do you think there’s other intelligent life in the universe?
What’s your take on “cancel culture“?
What’s your opinion on taking risks?
How do you feel about self-help books?
What’s more important to you: work-life balance or climbing the career ladder?
How do you feel about the education system?
What’s your stance on climate change and renewable energy?
How do you feel about diets and health trends?
What are your thoughts on parenting styles?
Do you believe in second chances?
How do you feel about open relationships?
What’s your opinion on consumerism?
What’s your stance on animal rights?
How do you feel about reality TV?
Do you think age is just a number, or is it important?
How do you feel about extreme sports?
What’s your opinion on people moving abroad for better opportunities?
What’s your take on artificial intelligence?
Do you think we’re too dependent on technology?
What’s your idea of justice?

Frequently Asked Questions

What should I avoid when asking questions?

Being Too Personal, Too Soon: Avoid sensitive topics like religion, politics, or past relationships unless the other person brings it up and seems comfortable discussing it.
Interrogation Style: Bombarding someone with questions can make it feel like an interview, not a conversation.
Ignoring Discomfort: If the other person seems uneasy, it might be best to change the subject.

What if the conversation stalls or hits an awkward pause?

Awkward moments happen to everyone. Having a few ‘go-to‘ questions in your back pocket can help reignite the conversation. But also, sometimes a pause is just a pause; it’s okay to let the conversation breathe.