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241 Questions to Ask a Guy on a Date, In-Person, or Via Text

There are plenty of good questions to ask a guy to find out what you need to know.

Did you know that a failure to ask any questions on a date is a major red flag? Dating experts suggest that while the behavior might not be malicious, it is indicative of someone who doesn't often pay attention to other people's feelings. Dragging that habit into a relationship spells even more bad news. An inability to ask your partner questions creates distance. It can also complicate a pair's ability to problem-solve. Don't worry, though. Even if you've dodged the duty in the past, there are easy ways to make up for it now. All you need to do is think up a few questions and, well, ask them. And if you don't know where to start, keep reading—especially if you're prepping for an encounter with someone of the male variety. We've put together a comprehensive list of questions to ask a guy during your next night out.

READ THIS NEXT: 228 Questions to Ask a Girl During Your Next Date.

Fun Questions to Ask a Guy When Flirting

Don't fret, the questions are coming. And it's a good thing too because dating isn't easy. You have to be attentive, express interest, display charm, and so many other things that may not come naturally. The worst part? You also have to keep an eye out for lulls in the conversation. If one comes, you've got to squash it fast. That's where we come in. Sort through the questions below to help keep the wheels turning.

Helpful Ice-Breakers

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  1. What's something you refuse to spend money on?
  2. What's your biggest guilty pleasure?
  3. What's your favorite holiday?
  4. What's your favorite movie?
  5. Do you consider yourself a foodie?
  6. What's one song that you never get sick of?
  7. What's one musical instrument you wish you knew how to play?
  8. Do you have a favorite author?
  9. Do you speak any other languages?
  10. What's your favorite video game?
  11. What was the last movie you saw in theaters?
  12. What network is your favorite show on?
  13. What's your favorite way to relax?
  14. What do you think has better material, Hulu or Netflix?
  15. What's one thing you've never been good at?
  16. What's your favorite fast food restaurant?
  17. What's your favorite food of all time?
  18. What's your mother's name?
  19. Where are you from?
  20. What's one website that you visit every day (email doesn't count)?
  21. Do you prefer the mountains to the ocean? Or the other way around?
  22. What's your favorite song?
  23. Did you play sports as a kid?
  24. What do you think your best quality is?
  25. …What about your worst?
  26. Do you prefer going out or staying in on Saturday nights?
  27. What subject did your favorite teacher from high school teach?
  28. Do you prefer a good movie or a good book?
  29. Do you have any useless skills?
  30. What food grosses you out?
  31. Do you like old films?
  32. Would you ever vacation in the same place twice?

READ THIS NEXT: 271 Questions to Ask Your Boyfriend Before Getting Serious.

Silly Questions to Ask Over Text

silly questions to ask a guy - couple on a date
Shutterstock / Song_about_summer
  1. What's the weirdest thing on your bucket list?
  2. What's something you really stressed over that wound up being no big deal?
  3. What's one food that you could eat every day for the rest of your life?
  4. Do you have a favorite cartoon?
  5. Do you know how to juggle?
  6. What's a scene from a movie that you wish you could recreate in real life?
  7. How many plants do you have in your apartment?
  8. What's the weirdest thing you've ever done to impress a potential love interest?
  9. What's the weirdest dream you've ever had?
  10. What's the best flavor combination for ice cream?
  11. If you were granted three wishes, what would you ask for?
  12. If you were a superhero, what kind of secret identity would you have?
  13. What's the best prank you ever pulled on someone?
  14. If you had a boat, what would you name it?
  15. Do you sleep naked?
  16. What's the most scandalous photo you've ever sent a crush?
  17. What's the meanest thing you've ever said to your parents?
  18. What's something you're glad you'll never have to do again?
  19. What's something that always makes you smile?
  20. Have you ever faked it in the bedroom?
  21. If you had to get rid of one of your five senses, which would you give up?
  22. Do you believe in aphrodisiacs?
  23. What was your favorite toy as a kid?
  24. What time do you usually wake up in the morning?
  25. If you had a catchphrase, what would it be?
  26. What's the weirdest thing that's happened to you this week?
  27. If you inherited a billion dollars, what would you buy first?
  28. What's your favorite pet name for a girlfriend?
  29. Which do you like better, dogs or cats?
  30. If you had a time machine, which era would you choose to visit?
  31. What game show would you go on to win money?
  32. Who would you choose to play you in a movie?
  33. Do you have a go-to karaoke song?
  34. Were you a boy scout?
  35. Do you like music festivals?
  36. What's your most expensive hobby?
  37. Do you know how to pick a lock?

READ THIS NEXT: 21 Questions to Ask in a New Relationship

Funny Questions to Ask a Guy

couple laughing - funny questions to ask a guy
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  1. Which fictional character would you date?
  2. What's your most embarrassing moment from high school?
  3. Who's your favorite family member?
  4. What's the worst lie you've ever told?
  5. What's your weirdest habit?
  6. Does your car have a name?
  7. How often are you on TikTok?
  8. Who do you think is the most handsome male actor working today?
  9. Do you prefer being the big spoon or the little spoon?
  10. Have you ever worn a dress in public?
  11. Can you do any good impressions?
  12. If asked to describe you, what's the worst thing that your friends might say?
  13. What's the most embarrassing thing you've ever done on a first date?
  14. Do you ever double-text?
  15. Are you awkward around kids?
  16. So, do you work out?
  17. Have you ever worn make-up?
  18. Do you snore?
  19. Do you know the lyrics to any Broadway tunes?
  20. Would you ever grow your hair long?
  21. Are you afraid of birds?
  22. What do you think about pineapple on pizza?
  23. How many times do you snooze your alarm in the morning?
  24. What's one thing you wish more women understood about men?
  25. Do you like going to brunch?
  26. Have you ever gotten a manicure?
  27. What's your biggest turn-off?
  28. What do you like most about dating?
  29. Do you know how to change a tire?
  30. What's the weirdest bet you've ever made?
  31. What crimes would you commit if you knew you'd never get caught?

READ THIS NEXT: 50 Cute Things to Say to Your Boyfriend Every Day.

Interesting Questions to Get to Know Someone

couple smiling at restaurant - good questions to ask a guy
Shutterstock / Fergus Coyle
  1. What's your dream job?
  2. Which historical figure do you admire most?
  3. What's more important: being attracted to someone or being able to have an interesting conversation with them?
  4. How old were you when you had your first kiss?
  5. Who's your celebrity crush?
  6. Do you believe in aliens?
  7. At what age do you hope to retire?
  8. Do you like to stick to a schedule or play things by ear?
  9. Do you prefer watching movies alone or with other people?
  10. Do you have any pets?
  11. What's the most significant physical challenge you've ever faced?
  12. And what's the most significant mental challenge you've gotten over?
  13. What's something that gets you angry fast?
  14. Do you have a favorite quote?
  15. What's your favorite time of year?
  16. Are you good with computers?
  17. Would you rather be rich or famous?
  18. Do you want to have kids one day?
  19. What's one behavior that would make even the most beautiful person seem unattractive?
  20. Are you closer to your mother or your father?
  21. What was the last serious conversation you had with a potential love interest?
  22. If you could only bring three items to a desert island, what would you pack?
  23. In three sentences or less, describe your dream girl.
  24. What's something you would like to do for a date night?
  25. What was one story you loved as a little kid?
  26. What would you choose for your last meal?
  27. What's your earliest memory?
  28. Do you like where you grew up?
  29. Do you believe in the sanctity of marriage?
  30. Do you like surprises?
  31. How do you handle rejection?
  32. Do you like theme parties?
  33. What do you call your grandparents?
  34. What's the nicest compliment you've ever received?
  35. Are you friends with any of your exes?
  36. Do you prefer exercising alone or with a group?
  37. What do you like to do on a day off?
  38. Do you prefer dive bars or dance clubs?
  39. If you had the opportunity to go back to school, what would you study?

Deep Questions to Ask

couple having a series conversation
Shutterstock / fizkes
  1. What's your favorite childhood memory?
  2. Why did your last relationship end?
  3. What's one piece of advice you would give to your younger self?
  4. What's your definition of a healthy relationship?
  5. What's your favorite family memory?
  6. Where do you see yourself in five years?
  7. Is there anything that you would change about your life?
  8. Do you consider yourself a spiritual person?
  9. Have you ever broken someone's heart?
  10. What's your biggest regret?
  11. Do you usually make decisions with your head or with your heart?
  12. What cultural norms do you hope to see change over the next few years?
  13. How important is physical appearance to you?
  14. Who's your favorite person in the world?
  15. What's your love language?
  16. Have you ever been addicted to something?
  17. What would you never allow someone to do to you?
  18. What's something you're grateful for that's happened over the past year?
  19. How would your behavior change if tomorrow you woke up without any fear?
  20. What activity makes you feel most like yourself?
  21. What motivates you to get up in the morning?
  22. Have you ever been in love?
  23. How has your sense of right and wrong evolved over the years?
  24. What's one mistake that you'll never do again?
  25. Have you ever been heartbroken?
  26. How can you tell when someone is lying?
  27. Would you marry someone outside of your faith?
  28. What's the most meaningful gift you've ever been given?
  29. What's something people usually get wrong about you?
  30. Have you ever cheated on a significant other?
  31. Have you ever been cheated on?
  32. When do you think it's OK to tell a lie?
  33. What was the longest relationship you've ever had?
  34. …and the shortest?
  35. Do you think any topics are too taboo to talk about on a first date?
  36. What was the proudest moment of your life?
  37. If you could organize the perfect date, where would you go?
  38. Do you believe in soulmates?
  39. What's your biggest phobia?
  40. Do you consider yourself a feminist?
  41. What's something you would do more often if you weren't worried about being judged for it?

READ THIS NEXT: 236 Important Questions to Ask Your Girlfriend

Fun Questions to Ask on the First Date

couple laughing over coffee - good questions to ask a guy
Shutterstock / Dragon Images
  1. What's your favorite ice cream flavor?
  2. Do you believe in love at first sight?
  3. How long you have known your best friend?
  4. Are you a morning person or a night person?
  5. What's your most prized possession?
  6. What's the funniest movie you've ever seen?
  7. What's your ideal Saturday night?
  8. Are you a night owl?
  9. What's something that absolutely terrified you as a kid?
  10. Describe a time when you really stepped out of your comfort zone.
  11. What's your favorite Martin Scorsese movie?
  12. What's your biggest turn-on?
  13. Describe your first crush.
  14. Do you have a favorite joke?
  15. Do you have a favorite podcast?
  16. Do you have any recurring dreams?
  17. If you had the chance to be on reality television, would you take it?
  18. If you could move to any other country, where would you go?
  19. If you could trade lives with anyone in the world, who would you choose?
  20. Do you like to cuddle?
  21. In your opinion, what's the most fun way to travel?
  22. Do you believe in astrology?
  23. What's your favorite time of day?
  24. Do you believe in past lives?
  25. Have you ever had a fling with someone from work?
  26. What's the next book you want to read?
  27. What are your favorite pizza toppings?
  28. What do you think your most feminine quality is?
  29. If you could learn one language with the snap of your fingers, what would it be?
  30. What's the best piece of dating advice you've ever received from a friend?
  31. Do you believe in any superstitions?

READ THIS NEXT: 75 Relationship Quotes to Reignite Your Love.

Flirty Questions About You

woman flirting with man
Shutterstock / Dmytro Zinkevych
  1. What's your favorite physical feature on me?
  2. If I were an animal what would I be?
  3. How old do you think I was when I had my first kiss?
  4. What's my favorite color?
  5. What sets me apart from other people you've dated?
  6. Do you like what I'm wearing?
  7. What's my natural hair color?
  8. Where are you going to take me for our second date?
  9. Would you say that I'm your usual type?
  10. How do you think I like my coffee?
  11. What do you think my superpower is?
  12. What was your first impression of me?
  13. Do you think I'm the oldest kid in my family or the youngest?
  14. Do I seem shy or outgoing?
  15. Do I seem like a good driver?
  16. What do you think my nickname was growing up?
  17. Can you guess my middle name?
  18. What do you think my first job was?
  19. What do you think is my best quality?
  20. How often do you think I date?
  21. What do you think my bedroom looks like?
  22. How many books do you think I've read over the past year?
  23. What social media app do you think I spend the most time on?
  24. What do you think I do for work?
  25. How old do you think I was when I got my first job?
  26. Do you think I've had a lot of boyfriends in the past?
  27. What do you think my favorite hobby is?
  28. What do you think I usually order at a restaurant?
  29. What kind of cocktail should I drink?
  30. What do you think I know most about in this world?

Wrapping Up

That's it for our list of questions to ask a guy during your next date, but be sure to check back in with us soon! Best Life is committed to helping you find the right words for any occasion. Sign up for our newsletter to enjoy similar kinds of content, as well as hit pieces on health, entertainment, and travel.

Carrie Weisman
Carrie Weisman oversees all SEO efforts at Best Life. She specializes in content optimization and editorial marketing. Read more
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