Getting to know someone you like can be exciting, but it can also be a bit tricky.
You want to make sure the conversation flows naturally while also learning more about his personality, interests, and values.
The key to building a connection is asking thoughtful questions that help you understand him better.
Whether you’re on a date, in a casual hangout, or just having a conversation over text, here are 120 questions to ask a guy you like to get to know him in a fun and engaging way!
Personal Background Questions
- Where did you grow up?
- Do you have any siblings?
- What’s your favorite childhood memory?
- What’s something about you that not many people know?
- How would you describe your family dynamic?
- Who is the most influential person in your life?
- What’s one thing you’ve always wanted to do but haven’t yet?
- If you could live anywhere in the world, where would it be?
- Do you believe in astrology or have any favorite zodiac signs?
- What’s your relationship like with your parents?
Hobbies and Interests
- What’s your favorite way to spend your free time?
- Do you have any hidden talents?
- What type of music do you listen to the most?
- Have you ever played a musical instrument?
- What’s your all-time favorite movie?
- Do you prefer reading books or watching TV shows?
- What’s the last book you read?
- Do you like to travel? What’s your dream vacation spot?
- Are you into any sports? Which one is your favorite to play or watch?
- What’s something you’re passionate about?
Career and Ambitions
- What do you do for work?
- Is there a career you’ve always dreamed of?
- Do you enjoy your job or wish you were doing something else?
- What would you do if you weren’t in your current profession?
- Are you more of a “9-to-5” person or do you enjoy working outside those hours?
- What motivates you to work hard?
- Do you prefer a stable career or one that involves a lot of changes and challenges?
- Where do you see yourself in five years?
- What’s a professional achievement you’re really proud of?
- What’s your biggest work-related pet peeve?
Lifestyle and Values
- Are you an early riser or a night owl?
- How do you like to unwind after a long day?
- Do you prefer going out or staying in?
- How important is physical fitness to you?
- What’s your idea of a perfect weekend?
- Are you a spender or a saver?
- What’s your favorite type of food to eat?
- Do you prefer cooking at home or dining out?
- What’s the most adventurous thing you’ve done?
- Do you believe in fate or destiny?
Relationship and Love Life
- What do you look for in a relationship?
- What’s your love language?
- Have you ever been in love?
- Do you believe in soulmates?
- What’s your idea of a perfect date?
- Are you a romantic person?
- How do you show someone you care about them?
- What’s the best relationship advice you’ve ever received?
- Do you think it’s important to be friends first in a relationship?
- What’s something you’d want to change about relationships today?
Fun and Quirky Questions
- If you could switch lives with anyone for a day, who would it be?
- What would you do with a million dollars?
- What’s the weirdest food you’ve ever tried and liked?
- What’s something you’ve always wanted to try but haven’t yet?
- If you could have any superpower, what would it be?
- Do you believe in ghosts or aliens?
- What’s your guilty pleasure?
- What’s the funniest thing you’ve ever done on a dare?
- If you could live in any fictional world, where would it be?
- What’s the worst haircut you’ve ever had?
Philosophical and Deep Questions
- Do you believe in the concept of good and evil?
- What do you think happens after we die?
- Do you think we have control over our own destiny?
- What’s your biggest fear?
- Do you believe in second chances?
- How do you define success?
- What’s one lesson you’ve learned the hard way?
- How do you handle stress or difficult situations?
- What’s something you value above all else?
- If you could change one thing about the world, what would it be?
Social and Cultural
- What’s your favorite holiday and why?
- Do you have a favorite place in the city you live in?
- Are you into fashion? What’s your personal style?
- What’s your opinion on social media?
- Do you think it’s important to be active in politics?
- How do you feel about public speaking?
- What’s the best concert you’ve ever been to?
- Do you prefer big gatherings or small get-togethers?
- How do you feel about social issues like climate change and inequality?
- What’s your favorite TV show right now?
Future Goals and Aspirations
- What’s something you’ve always wanted to learn but haven’t yet?
- What are your long-term goals in life?
- How do you plan to make a difference in the world?
- What’s one personal goal you’re working on right now?
- Do you believe in the concept of “following your dreams”?
- What’s something that excites you about the future?
- Do you see yourself getting married one day?
- What do you think makes someone successful in life?
- Would you ever consider moving to a different country?
- What’s your biggest aspiration in life?
Hypothetical and Fun Scenarios
- If you could have dinner with any three people, dead or alive, who would they be?
- What would you do if you found out you only had a week to live?
- If you could change one thing about your past, what would it be?
- What would you do if you could time travel?
- If you could master any skill instantly, what would it be?
- What would your dream house look like?
- If you could be famous for one thing, what would it be?
- What’s the craziest thing you would do for a million dollars?
- If you had a time machine, what period of history would you visit?
- What would you do if you could be invisible for a day?
Random Fun Facts
- What’s the best gift you’ve ever received?
- What’s your all-time favorite board game or video game?
- Do you like going to the beach or the mountains more?
- If you could have any animal as a pet, what would it be?
- What’s your favorite season of the year?
- Do you believe in luck?
- What’s something you wish people knew about you?
- Do you have any phobias?
- If you could have dinner with a celebrity, who would it be?
- What’s your favorite time of day—morning, afternoon, or night?
Reflective and Thoughtful
- When was the last time you helped someone, and how did it make you feel?
- What’s one thing you’re grateful for today?
- How do you stay motivated when things get tough?
- Do you think people can truly change?
- How do you express your feelings when you’re upset?
- What’s one thing you think is really important in a friendship?
- Do you consider yourself more of an optimist or a realist?
- What’s the most important lesson life has taught you so far?
- What do you appreciate most about the people in your life?
- How would you like to be remembered?
Conclusion
Asking the right questions can help you uncover the layers of someone’s personality and build a deeper connection.
Whether you’re just getting to know him or you’ve been talking for a while, these 120 questions to ask a guy you like, can make fun, interesting, and insightful conversations.
The key is to listen carefully, show genuine curiosity, and enjoy the process of learning about each other. Happy chatting!