100+ Flirty Questions to Ask a Guy Over Text

Just before we dive right into reeling out the sparkling flirty conversations starters, it's important to walk through the tone.

If your intention with these questions is to truly be flirty, then you need to be very strategic with it.

First, the type of flirty questions you want to explore have to be those that match the current status of your relationship. Of course, you don't want to be jumping into overly sexual flirty questions on the first video chat.

Instead, start small. Ask for what a perfect date feels like to him or if he believes in love at first sight.

But if you've established some prior connection, then you may want to set the pace. Throw in some flirty nicknames and study the body language over text. If he is receptive, then make your move by going to deeper flirty questions.

Very soon, you'll be able to have sparking flirty conversations without any inhibitions. When that happens, take advantage of our different cute flirty questions below.

Don't just flirt, but also ensure to have fun while at it. Thankfully, we have a good number of fun questions that you can choose from below.

1. What's your favorite thing to do on weekends?

   
   

2. What do you think is most useless invention of all time?

   
   

3. What's your go-to karaoke song?

   
   

4. Who is your most notable historical figure?

   
   

5. What is your favorite physical feature in a lady?

   
   

6. What is your favorite video game?

   
   

7. What is the most embarrassing thing you've ever done?

   
   

8. What have you been doing with your free time lately?

   
   

9. What's your biggest "holy shit why haven't I done this sooner" moment?

   
   

10. What's your funniest dating story?

    
    

11. Do you have a favorite joke?

    
    

12. Are you a night owl or early bird?

    
    

13. What's the most exciting place you've ever visited?

    
    

14. Do you believe in astrology? What's your zodiac sign?

    
    

15. Can I see the last selfie you took? What's the story behind it?

    
    

16. Are you a cat or dog person?

    
    

17. What's your favorite way to spend a rainy dinner?

    
    

18. What's your favorite cuisine? Should we try the dish together?

    
    

19. If you could have a superpower, what would it be?

    
    

20. What is your favorite slow dance move?

    
    

21. What unnecessary products do you consider necessary?

    
    

22. Would you rather wake up tomorrow as the opposite sex or 50 years older?

If you need flirty questions to ask a guy and make him think deeply, you're at the right place. These are open-ended questions that keep the conversation respectful but evoke very personal responses.

1. What's your biggest fear?

   
   

2. What's one lesson you learned from your past relationships?

   
   

3. What is your most attractive quality in the opposite sex?

   
   

4. What is the most adventurous thing you've ever done for love?

   
   

5. Do you believe in love at first sight?

   
   

6. What is the most memorable compliment you've ever received?

   
   

7. What is the most romantic thing anyone has ever done for you?

   
   

8. What is your biggest turn-on in a lady?

   
   

9. What non-sexual quality is your biggest turn-on in a lady?

   
   

10. What is your biggest regret as an adult?

    
    

11. Do you believe in soul mates?

    
    

12. What do you imagine would happen if we switched lives?

    
    

13. Would you rather spend a whole day or a whole night with me?

    
    

14. How direct would you want someone to be if they had feelings for you?

    
    

15. What do you think about right before you fall asleep?

    
    

16. What makes you feel safe with someone?

    
    

17. What's your favorite thing about being in a relationship?

    
    

18. What is the most thoughtful gift anyone has ever given you?

    
    

19. How do you feel cared for by a lady?

    
    

20. If there was one thing you could change about me, what would that be?

    
    

21. What wish would you ask for if a genie appeared before you?

For ice-breakers, no-context conversations, or something to just keep the discussion going, we recommend random flirty questions like the ones below.

1. What's your favorite ice cream flavor?

   
   

2. What's your dream job?

   
   

3. Do you prefer movie or restaurant dates?

   
   

4. What's your favorite childhood memory?

   
   

5. What song has been on repeat lately?

   
   

6. How did you meet your best friend?

   
   

7. Which do you prefer: hot dog or chicken sausage?

   
   

8. What is the title of your favorite movie of all time?

   
   

9. What's your favorite song?

   
   

10. Can you describe your dream woman in one word?

    
    

11. Do you think you can make a long distance relationship work?

    
    

12. Who is your female celebrity crush?

    
    

13. What is your guilty pleasure?

    
    

14. What is the most adventurous thing you've done as a child?

    
    

15. Is there a nickname you go by?

    
    

16. When last did you feel butterflies in your tummy?

    
    

17. What question are you hoping I'll ask you?

    
    

18. What was your first impression of me?

    
    

19. What part of your daily routine do you always look forward to?

    
    

20. Do you have any secret crush?

    
    

21. If you were an ice cream flavor, what would you be?

    
    

22. What is the weirdest thing you've ever eaten?

    
    

23. If you designed your ideal dating app, what would it look like?

Build an emotional connection from scratch with subtle flirty questions. These questions are straight to the point and yet aren't overly forward in a way that'd trigger a negative response.

1. What's your idea of a perfect date?

   
   

2. What's your idea of the best surprise date?

   
   

3. Do you still speak to your high school crush?

   
   

4. Do you prefer cuddling or kissing?

   
   

5. How quickly do you fall asleep at night?

   
   

6. What is your best romantic movie of all time?

   
   

7. Do you enjoy flirty conversations?

   
   

8. When did you have your first kiss?

   
   

9. What secret fantasies do you wish to explore with me?

   
   

10. Where will you go on first date?

    
    

11. Do you believe in love at first sight?

    
    

12. What's a must-have for a perfect kiss?

    
    

13. For how long can you keep romance alive?

    
    

14. What is your favorite memory from a time you were in love?

    
    

15. What attractive quality do you look out for on the first date?

    
    

16. Do you prefer to make the first move?

    
    

17. How soon do you think a new couple can take a vacation together?

    
    

18. What made you happiest in your former relationship, assuming you had one?

    
    

19. Do you believe in love potions?

    
    

20. What's your favorite part of your body? Can I guess it?

    
    

21. Where is the craziest place you've ever had sex?

If you are bold enough to ask the more direct questions, then our cheeky flirty questions to ask a guy are your best bet. This category of flirty questions is wide-ranging and introduces the much-needed erotic spark.

1. What is your love language?

   
   

2. What do you like more? Cuddling or kissing?

   
   

3. Who is your most loved fictional character from a TV show?

   
   

4. Have you ever gone skinny dipping?

   
   

5. Who is your most loved fictional character from a movie?

   
   

6. Have you ever had a one-night stand?

   
   

7. What is your current relationship status?

   
   

8. What is the best compliment you have ever received?

   
   

9. What item or activity are you looking to get off your bucket list?

   
   

10. What secret fantasy would you like to explore if we were together?

    
    

11. Describe your dream woman in three words?

    
    

12. Did you always have this habit of stealing hearts?

    
    

13. What color is the underwear I'm wearing now?

    
    

14. If I asked you to take off one piece of clothing from me, what would you pick?

    
    

15. Little spoon or big spoon?

    
    

16. What is the cheesiest pick-up line anyone's ever tried on you? Did you like it?

    
    

17. What's a romantic quote you love?

    
    

18. What's your idea of the perfect weekend getaway?

    
    

19. What's the most disturbing thing under your bed?

    
    

20. Which is better: makeup sex or breakup sex?