153 questions to ask the guy you’re talking to

Real talk: keeping a conversation going with a guy — especially one you, ahem, like — can be tricky sometimes. Fortunately, we have the perfect solution to fill any awkward silence that may befall your talking stage: asking questions. Whether you’re looking to strike up a conversation with your crush, spice up a run-of-the-mill convo with your partner by asking some sexy questions, or looking to get to know your long-term love even better than you already do, asking questions is a great way to strengthen your bond, reheat a lukewarm text sesh, or just get better acquainted with someone you have your eye on. Hence why it’s always a good idea to have a handy list of questions to ask a guy in your back pocket — and hence why we’ve rounded up this list of options for your inspiration.

Now, you don’t want to just rattle off random questions at the dude like it’s an interrogation. (That said, suggesting a round of 21 Questions is actually a great way to revive a fading text convo.) Ideally, you’ll want to, uh, actually pay attention to what he’s saying and respond with relevant Qs that encourage him to go into more detail. But if you need to break an awkward silence or rekindle a flagging conversation, dropping a fun and thought-provoking question can be just the thing to get the vibes back on track.

Should you find yourself in need of a little inspo, here are 153 questions to ask a guy, from light and low key to fun and flirty to hot and heavy. Keep these in mind for your next date night or sprinkle them into tonight’s texting convo, and I can assure you no awkward silence will go unfilled.

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. Would you still love me if I were a worm?

4. Who would play you in a movie about you?

5. What’s your most controversial food opinion?

6. What’s your favourite food that everyone else thinks is gross?

7. If you had to get a tattoo today, what would you get?

8. Which is the superior genre of breakfast foods: sweet or savoury?

9. What’s a conspiracy theory you actually believe in?

10. Who is your celebrity doppelgänger?

11. What’s one thing that’s considered cringe that you love anyway? (Your cringey pleasure?)

12. How often do you think about the Roman Empire?

13. What’s the most overrated thing that everyone else is obsessed with?

14. What’s your favourite chocolate bar?

15. What’s your go-to cinema snack?

16. Do you have feelings about pineapple on pizza?

17. What’s the most cringe trend of the moment?

18. What’s your social media platform of choice?

Fun questions to ask a guy (for good vibes only)

1. What’s your star 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 high school?

5. What’s one thing your parents don’t know about you?

6. What are your top three vices?

7. What’s your personality test of choice? (Is he a Myers-Briggs guy? An astrology fan? An Enneagram devotee?)

8. Do you think you’re a good driver?

9. What kind of person are you at parties?

10. What’s your drink of choice?

11. If you could only eat one thing for the rest of your life, what would it be?

12. 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.)

13. If you could get on a plane right now and go anywhere, where would you go?

14. Have you ever done anything illegal?

15. 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 you saw today?

Flirty questions to ask a guy (when you wanna be cute)

1. What do you call me when you talk to your friends about me?

2. When was the last time you had a crush?

3. When are you going to ask me out?

4. Do you think you have a type?

5. What’s one thing you saw today that made you think of me?

6. Do you remember your first kiss?

7. Who was your first crush?

8. How do you know when you have a crush on someone?

9. Do you believe in love at first sight?

10. Have you ever been in love?

11. When was the last time you were in love?

12. What’s one thing you haven’t told me that you want to?

13. What do you think makes a good kisser?

14. Who is your celebrity crush?

15. 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.)

16. What’s your love language?

Sexy questions to ask a guy (when you want to heat things up a bit)

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. What sex position/sex act do you think is overrated?

8. What’s something you wish you knew about sex before you had it for the first time?

9. What kind of porn do you watch?

10. What do you masturbate to? (Porn? Imagination? 18th-century erotica?)

11. Do you consider yourself kinky?

12. What’s one thing you were surprised to find out you were into in bed?

13. What’s the number one thing on your sex bucket list right now?

14. Thoughts on group sex?

15. What’s one sex thing you’ve tried and don’t want to do again?

16. Do you have sex dreams?

17. Do you prefer morning sex or night sex?

18. Shower sex: hot or overrated?

19. How often do you masturbate?

20. Do you like to initiate?

Deep questions to ask a guy (when you’re ready to get into it)

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 favourite thing about your best friend?

9. What’s your favourite 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 defence mechanism?

21. What’s the most important thing you’ve learned in therapy?

Questions to ask a guy about dating and relationships (so you know what you’re getting into)

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 sex on the first date?

9. When was your last serious relationship?

10. Do you think you’ll ever get married?

11. What would you do if you were dating someone your friends didn’t like?

12. Have you ever cheated on a partner?

13. Have you ever been cheated on?

14. What was your hardest break-up?

15. What’s one thing you learned from your last relationship?

16. What’s your biggest fear about relationships?

17. What’s your favourite thing about being in a relationship?

18. What’s your favourite thing about being single?

19. What’s your biggest dating red flag?

20. What’s my beige flag?

21. Do you think you’re a Golden Retriever Boyfriend?

Questions to ask a guy to get to know each other better (so you know what you’re working with)

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 takeaway person?

8. What’s one thing you miss about your hometown?

9. What was your favourite 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 a guy if you’ve been together for a minute (bc there’s always more to know!)

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 favourite memory from the past year?

8. Where should we go on our next vacation?

9. What’s one misconception you think people have about us as a couple?

10. Where do you see us five years from now?

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