160 Questions to Ask a Guy That Will Capture His Attention

Let’s face it: figuring out what to ask a guy can sometimes feel like walking a tightrope. Too casual, and you risk sounding uninterested. Too deep, and he might wonder if he’s on a surprise job interview.

The sweet spot? Questions that feel natural but also keep him curious and engaged.

This list is here to make your life easier! Whether you want to make him laugh, uncover his deepest thoughts, or casually flirt without overdoing it, you’ll find just the thing to keep the conversation going—and maybe even leave him thinking, “Wow, she’s really something.“

Personal Questions to Ask a Guy To Get to Know Him

1. What’s your favorite way to spend a lazy day?
2. How do you usually handle stress?
3. Do you consider yourself more introverted or extroverted?
4. What’s a hobby or activity you enjoy most?
5. What’s your relationship with your family like?
6. What’s one thing you wish more people knew about you?
7. How do you usually celebrate achievements?
8. What’s your favorite kind of vacation?
9. Do you believe in fate or free will?
10. What’s one thing you’ve done that you’re proud of?
11. How do you handle criticism?
12. What’s your favorite way to spend time with friends?
13. What’s one thing you couldn’t live without?
14. How do you usually make decisions?
15. What’s your favorite kind of food or cuisine?
16. Do you consider yourself a morning person or a night owl?
17. What’s your go-to way to cheer yourself up?
18. Do you prefer big social events or smaller gatherings?
19. What’s your ideal way to spend a weekend?
20. What’s one habit you’re trying to improve?

Deep Questions to Ask a Guy

1. What’s one life lesson you’ve learned the hard way?
2. What motivates you to keep going during tough times?
3. Do you believe everything happens for a reason?
4. What’s a childhood memory that shaped who you are today?
5. How do you handle failure or rejection?
6. What do you think is the meaning of happiness?
7. What’s your biggest fear, and why?
8. Who has influenced you the most in life?
9. If you could change one thing about your past, what would it be?
10. How do you usually express your emotions?
11. What’s a goal you’re currently working towards?
12. How do you define success in life?
13. What’s one thing you’d like to be remembered for?
14. Do you believe people can truly change?
15. What role does family play in your life?
16. What’s one decision you made that you’re proud of?
17. Do you consider yourself more logical or emotional?
18. What’s a personal value you would never compromise?
19. How do you handle conflict in relationships?
20. What’s one thing you’re most grateful for right now?

Funny Questions to Ask a Guy

1. If you could only eat one food for the rest of your life, what would it be?
2. What’s the weirdest thing you’ve ever Googled?
3. Would you rather have the ability to talk to animals or read minds?
4. What’s the most embarrassing thing that’s ever happened to you?
5. If you were a superhero, what would your superpower be?
6. What’s the worst pickup line you’ve ever heard or used?
7. If you could swap lives with a celebrity for a day, who would it be?
8. What’s the strangest food combination you secretly love?
9. If you were in a zombie apocalypse, what’s the first thing you’d do?
10. What’s a ridiculous fear you’ve had since childhood?
11. If you could star in any movie, what genre would it be?
12. What’s the worst fashion trend you’ve ever tried?
13. Would you rather fight one horse-sized duck or 100 duck-sized horses?
14. What’s your guilty pleasure TV show or movie?
15. If you could instantly master a skill, what would it be?
16. What’s the worst haircut you’ve ever had?
17. If aliens landed tomorrow, what’s the first thing you’d say to them?
18. What’s the most ridiculous thing you’ve ever bought?
19. If you had to create a new holiday, what would it celebrate?
20. Would you rather always have to sing instead of talk or dance instead of walk?

Good Questions to Ask a Guy

1. What’s the best compliment you’ve ever received?
2. If you could live anywhere in the world, where would it be?
3. What’s your dream job or career path?
4. Do you believe in second chances?
5. What’s your favorite thing to do on weekends?
6. What’s one skill you wish you had?
7. How do you usually spend your holidays?
8. What’s your go-to way to relax after a long day?
9. What’s the best piece of advice you’ve ever received?
10. What do you value most in a friendship?
11. What’s one thing you’ve always wanted to try but haven’t yet?
12. What’s your favorite childhood memory?
13. If you won the lottery, what’s the first thing you’d do?
14. How do you usually celebrate your birthday?
15. What’s one thing you’re really passionate about?
16. If you could relive any moment in your life, what would it be?
17. What’s your favorite type of music or band?
18. How do you usually spend your time off work?
19. What’s a book or movie that inspired you?
20. If you could trade lives with anyone for a week, who would it be?

Interesting Questions to Ask a Guy

1. If you could time travel, would you visit the past or the future?
2. What’s the most fascinating place you’ve ever visited?
3. If you could meet any historical figure, who would it be?
4. What’s one invention you wish existed?
5. What’s a skill you think everyone should learn?
6. If you could live in any era, which one would you choose?
7. What’s a conspiracy theory you secretly think could be true?
8. If you could master one musical instrument, what would it be?
9. What’s one thing you’ve always been curious about?
10. What’s your favorite piece of random trivia?
11. If you could swap jobs with anyone, who would it be?
12. What’s the coolest thing you’ve ever learned?
13. If you could speak any language fluently, which would it be?
14. What’s one thing you wish you were better at?
15. If you could live in a movie universe, which one would it be?
16. What’s a new trend or technology you find exciting?
17. If you could instantly gain expertise in any subject, what would it be?
18. What’s the most adventurous thing you’ve ever done?
19. If you could change one law or rule, what would it be?
20. What’s a question you’ve always wanted someone to ask you?

Flirty Questions to Ask a Guy

1. What’s the first thing you notice about a girl?
2. If you could take me anywhere on a date, where would it be?
3. What’s your idea of the perfect kiss?
4. Do you think you’re more charming in person or over text?
5. What’s one thing about me that you find attractive?
6. How do you usually flirt with someone you like?
7. What would you do if I said I was crushing on you?
8. Do you believe in love at first sight, or should I walk by again?
9. What’s one thing you find irresistible in a girl?
10. If I asked you to plan a romantic evening, what would it include?
11. How would you describe your perfect girlfriend?
12. What’s the most romantic thing you’ve ever done for someone?
13. What’s your favorite compliment to receive?
14. If I dared you to make me blush, what would you say?
15. Do you prefer a girl who’s mysterious or completely open?
16. What’s your favorite type of cuddle—spooning or something else?
17. Would you ever write someone a love letter?
18. What’s one thing about me you think I don’t realize is attractive?
19. Do you believe in soulmates, and why?
20. What’s your favorite way to show someone you’re interested?

Dirty Questions to Ask a Guy

1. What’s the sexiest thing a girl could wear?
2. What’s your biggest turn-on?
3. Do you prefer being the one in control or letting someone else take the lead?
4. What’s your wildest fantasy?
5. What’s your favorite part of foreplay?
6. Have you ever had a dream about me?
7. What’s the most daring thing you’ve ever done in the bedroom?
8. If I whispered in your ear right now, what would you want me to say?
9. What’s one thing you’ve always wanted to try but haven’t yet?
10. How do you feel about public displays of affection?
11. What’s the most romantic or sensual thing you’ve ever experienced?
12. If we were alone right now, what’s the first thing you’d want to do?
13. What’s your favorite way to be kissed?
14. Do you prefer slow and passionate or wild and spontaneous?
15. What’s the most exciting place you’ve ever gotten intimate?
16. What’s your favorite way to show someone you’re attracted to them?
17. If I asked you to describe your ideal romantic night, what would it include?
18. What’s one thing you’d love me to do that I probably haven’t thought of?
19. What’s a secret fantasy you’d only share with someone special?
20. Do you think physical chemistry is as important as emotional connection?

Random Questions to Ask a Guy

1. If you were stranded on a desert island, what three things would you bring?
2. What’s the last thing you binge-watched?
3. Do you believe in aliens?
4. What’s the weirdest dream you’ve ever had?
5. If you could live without sleeping, would you?
6. What’s your favorite random fun fact?
7. If you could own any animal as a pet, what would it be?
8. What’s the strangest habit you have?
9. If you could instantly learn one new skill, what would it be?
10. Do you believe in luck, or do we make our own fate?
11. What’s your favorite snack to eat at midnight?
12. What’s a random talent you have that most people don’t know about?
13. If you could pick any superpower, what would it be?
14. What’s the most spontaneous thing you’ve ever done?
15. What’s a totally useless skill you’ve mastered?
16. If you could have dinner with any fictional character, who would it be?
17. What’s your favorite kind of weather?
18. What’s a song you could listen to on repeat forever?
19. What’s your favorite holiday and why?
20. If you could live in any fictional universe, which one would it be?

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Final Thoughts

Conversations don’t have to be complicated. Sometimes, all it takes is the right question to turn an ordinary moment into something unforgettable.

But don’t forget—conversations are a two-way street. Be curious, but also open up and share your own thoughts. That’s how connections grow naturally and effortlessly.

So, whether you’re chatting over text, face-to-face, or somewhere in between, let these questions inspire you. Who knows? They might just lead to your best conversation yet.