Easy conversation that flows naturally is always a good sign that things are going well with someone you like, but let’s be real: Conversation isn’t easy for everyone. Some people are shy, and that doesn’t mean they don’t like you, it just means they might need a little time and direction to get comfortable. Enter: These handy questions to ask a guy, whether you’re on a first date, chatting with someone on a dating app, or trying to reheat a lukewarm text sesh with your crush.

Now, don’t get us wrong—anyone you’re on a date with should be making an effort to get to know you by asking you questions, too. The purpose of this list isn’t to make you the project manager of the conversation, it's to provide you with an extra tool you can lean on when the conversation goes dry or when you’ve already covered the basics but want to dive in a little deeper. Some of these questions are lighthearted, but many get straight to the heart of who someone is: how they grew up, what they’re looking for in a partner, and what their hopes and dreams look like for the future, among others.

And lest you think you can only ask these to someone new, not so! These questions can also come in handy on date night with your long-term partner, or even just when you’re hanging out with friends. People change! So even if you’ve been together forever, it’s important to keep talking and get to know who they are at this moment.

So without further ado, let’s dive into the questions! Keep this list bookmarked or copy and paste your faves into your Notes app for easy access. Get lost in the best convo of your life, thank us later.

Random Questions to Ask a Guy

  1. What would you re-name me if you could?
  2. If you could change your name, what would it be?
  3. What would you name our dog if we had one?
  4. Would you still love me/like me if I were a worm?
  5. Who would play you in a movie about you?
  6. What’s your most controversial food opinion?
  7. What’s your favorite food that everyone else thinks is gross?
  8. If you had to get a tattoo today, what would you get?
  9. If you had to get a piercing today, where would you get it?
  10. Which is the superior genre of breakfast foods: sweet or savory?
  11. What’s a conspiracy theory you actually believe in?
  12. Who is your celebrity doppelgänger?
  13. What’s one thing that’s considered cringe that you love anyway? (Your cringey pleasure?)
  14. How often do you think about the Roman Empire?
  15. What’s the most overrated thing that everyone else is obsessed with?
  16. What’s your favorite candy?
  17. What’s your go-to movie theater snack?
  18. Do you have feelings about pineapple on pizza?
  19. Ranch or ketchup?
  20. What’s the most cringe trend of the moment?
  21. What’s your social media platform of choice?

Fun Questions to Ask a Guy

  1. What’s your zodiac sign? (If he responds to this with some kind of eye-roll and/or stereotypical anti-astrology dude comment, that tells you everything you need to know.)
  2. Moon sign? (Bonus points if he also knows his rising, obvs.)
  3. What’s the number one thing you got in the most trouble for at school?
  4. What were you like in middle school/high school?
  5. How did you meet your best friend?
  6. What’s one thing your parents don’t know about you?
  7. What are your top three vices?
  8. What’s your personality test of choice? (Is he a Myers-Briggs guy? An astrology fan? An Enneagram devotee?)
  9. Do you think you’re a good driver?
  10. What kind of person are you at parties?
  11. What’s your drink of choice?
  12. If you could only eat one thing for the rest of your life, what would it be?
  13. What’s your most controversial opinion? (We’re talking like, “I don’t actually like dogs that much,” not like, “I don’t think women deserve rights,” BTW.)
  14. If you could get on a plane right now and go anywhere, where would you go?
  15. Have you ever done anything illegal?
  16. Do you remember your dreams?

Questions to Ask a Guy Over Text

  1. What was the weirdest thing that happened to you this week?
  2. If you could have anything for dinner tonight, what would it be?
  3. What would you make me for dinner tonight?
  4. Do you remember what you dreamed about last night?
  5. How many cups of coffee do you think you’ll need to get through this day?
  6. What are your top three emojis right now?
  7. Guess what emoji I’m thinking of right now?
  8. What’s the most random thought you had today?
  9. What made you laugh today?
  10. If you could’ve done anything you wanted to today, what would you have done?
  11. Phone calls, FaceTime, or texting—what’s your preference?
  12. Best meme or TikTok you saw today?
  13. What's the most recent song you listened to on Spotify?
  14. What was the last Youtube video you watched?
  15. What's in your Amazon cart right now?

Flirty Questions to Ask a Guy

  1. What do you call me when you talk to your friends about me?
  2. What made you want to swipe right on my profile? (If you met on a dating app.)
  3. When was the last time you had a crush?
  4. When are you going to ask me out?
  5. Do you think you have a type?
  6. What’s one thing you saw today that made you think of me?
  7. Do you remember your first kiss?
  8. Who was your first crush?
  9. How do you know when you have a crush on someone?
  10. Do you believe in love at first sight?
  11. Have you ever been in love?
  12. When was the last time you were in love?
  13. What’s one thing you haven’t told me that you want to?
  14. What do you think makes a good kisser?
  15. Who is your celebrity crush?
  16. Where would you take someone on a first date if you were trying to impress them? (Excellent way to inquire yourself into an impressive first date—hint hint.)
  17. What’s your love language?

Sexy Questions to Ask a Guy

  1. What physical feature are you most attracted to?
  2. If you could only have sex in one position for the rest of your life, what would it be? (This is a more fun twist on the classic “What’s your fave position?”)
  3. What do you think makes someone good in bed?
  4. What do you think makes you good in bed?
  5. What’s the weirdest place you’ve ever had sex?
  6. What do you remember most about the first time you had sex?
  7. Tell me about your first orgasm.
  8. What sex position/sex act do you think is overrated?
  9. What’s something you wish you knew about sex before you had it for the first time?
  10. What kind of porn do you watch?
  11. What do you masturbate to? (Porn? Imagination? 18th-century erotica?)
  12. Do you consider yourself kinky?
  13. What’s one thing you were surprised to find out you were into in bed?
  14. What’s the number one thing on your sex bucket list right now?
  15. Thoughts on group sex?
  16. What’s one sex thing you’ve tried and don’t want to do again?
  17. Do you have sex dreams?
  18. Do you prefer morning sex or night sex?
  19. Shower sex: hot or overrated?
  20. How often do you masturbate?
  21. Do you like to initiate?

Deep Questions to Ask a Guy

  1. What’s one thing you would change about your childhood?
  2. Which of your parents are you closest to and why?
  3. Which of your siblings are you closest to and why?
  4. What’s your biggest regret from your last relationship?
  5. Why did your last relationship end?
  6. What’s one thing you would say to your ex if you could?
  7. If you could go back in time and say one thing to anyone from your life, living or dead, what would it be?
  8. What’s your favorite thing about your best friend?
  9. What’s your favorite thing about yourself?
  10. What do you think is your worst quality?
  11. What is the biggest misconception people have about you?
  12. What’s your biggest fear?
  13. What’s the hardest thing you’ve ever been through?
  14. What’s one thing you’ll never do again that you wish you could?
  15. What’s one thing you thought you were too cool for when you were younger that you wish you’d just embraced?
  16. What’s the best advice you’ve ever received?
  17. What’s the worst advice you’ve ever taken?
  18. What’s one thing you wish you knew more about?
  19. What do you think is your biggest insecurity?
  20. What’s your biggest defense mechanism?
  21. What’s the most important thing you’ve learned in therapy?

Questions to Ask a Guy About Dating and Relationships

  1. Do you consider yourself a "relationship person"?
  2. Do you usually get broken up with, or do the breaking up?
  3. What makes a relationship “serious,” in your opinion?
  4. What are your thoughts on open relationships/non-monogamy?
  5. Do you like dating apps or do you prefer to meet people organically?
  6. What was your best first date?
  7. What’s one thing you like to know about someone before you go on a date with them?
  8. How do you feel about kissing on the first date?
  9. How do you feel about sex on the first date?
  10. When was your last serious relationship?
  11. Do you think you’ll ever get married?
  12. What would you do if you were dating someone your friends didn’t like?
  13. Have you ever cheated on a partner?
  14. Have you ever been cheated on?
  15. What was your hardest breakup?
  16. What’s one thing you learned from your last relationship?
  17. What’s your biggest fear about relationships?
  18. What’s your favorite thing about being in a relationship?
  19. What’s your favorite thing about being single?
  20. What’s your biggest dating red flag?
  21. What’s my beige flag?
  22. Are you a golden retriever or black cat boyfriend?

Questions to Ask a Guy to Get to Know Each Other Better

  1. Do you have siblings? Are you close with them?
  2. Are you a morning person or a night person?
  3. How would you describe your personal style?
  4. Do you consider yourself an introvert or an extrovert?
  5. Do you see yourself having kids someday or are you more of a cool uncle type?
  6. Do you have a big friend group or a small circle of close friends?
  7. Do you like to cook or are you more of a takeout person?
  8. What’s one thing you miss about your hometown?
  9. What was your favorite age and why?
  10. What was your dream job growing up?
  11. Do you like your job now?
  12. What do you do to calm down when you’re stressed?
  13. What was the last thing you laughed really hard over?
  14. What do you do to celebrate big news?
  15. If you had to move to another city tomorrow, where would you go?
  16. What was the last TV show you were obsessed with?
  17. What was the last book you couldn’t put down?
  18. What are your thoughts on attachment theory?
  19. What’s your attachment style?
  20. What’s your go-to comfort TV show that you watch over and over?

Questions to Ask Your Boyfriend or Husband

  1. What’s one thing you’ve never told me?
  2. What do you remember most about our first date?
  3. What’s one way you think you’ve changed since we started dating?
  4. What’s one thing you’ve never done that you want to do?
  5. If you could repeat one year of your life, which one would you choose?
  6. What’s one thing you wish we did more of?
  7. What's your favorite thing we do together?
  8. What's your favorite thing about our relationship?
  9. Why do you think we work as a couple?
  10. What’s your favorite memory from the past year?
  11. Where should we go on our next vacation?
  12. What’s one misconception you think people have about us as a couple?
  13. Is there anything that has surprised you about our relationship?
  14. Have any of your goals or dreams for the future changed since we first started dating?
  15. Are you where you wanted to be personally/professionally at this point?
  16. Has dating me helped change your perspective or opinion about anything?
  17. Where do you see us five years from now?