Cute, Fun, & Romantic Questions to Ask a Guy

PDF download Download Article
Conversation starters to spice things up and get to know him better
PDF download Download Article

You want to talk to your crush or boyfriend, but how do you do that when you get lost in those handsome eyes? Well, worry not because we’re here to help! We’ve compiled a list of the best flirty questions you can ask a guy (in person or over text) to start and keep the conversation going. Try these out on a first date, in the bedroom, or while you’re hanging out to say, “Hey, I’m into you.”

This article is based on an interview with our dating and relationship coach, Suzanna Mathews, founder of The Date Maven. Check out the full interview here.

Section 1 of 6:

Cute

PDF download Download Article
  2. 2
    What’s your favorite part of the day?
    Advertisement
  3. 3
    What was your first impression of me?
  4. 4
    What’s your idea of a perfect weekend?
  5. 5
    What’s something that always makes you smile?
  6. 6
    What’s something many people don’t know about you?
  7. 7
    What makes you laugh?
  8. 8
    Who’s the first person you call when something good happens?
  9. 9
    If I was a flower, what type of flower would I be?
  10. 10
    What do you think my favorite food is?
  12. 12
    How do you like to relax after a long day?
  13. 13
    What’s the best compliment you could receive?
  14. 14
    Do you like surprises?
  15. 15
    What’s something you could never live without?
  16. 16
    What do you think is the best part about being in a relationship?
  17. 17
    You can only pick one: sunsets or sunrises?
  18. 18
    What makes you happy?
  19. 19
    What meal would you cook to impress me?
  20. 20
    What are you thinking about?
    22. Advertisement
Section 2 of 6:

Fun

PDF download Download Article
  2. 2
    If you could go anywhere in the world, where would you go?
  3. 3
    If you were an animal, what would you be?
  4. 4
    Who’s your favorite fictional couple?
  5. 5
    What’s the best song of all time?
  6. 6
    What movie would you live in?
  7. 7
    If you could master any skill, what would it be?
  8. 8
    If you were a dessert, what would you be?
  9. 9
    What’s your favorite ice cream flavor?
  10. 10
    What’s the spiciest food you’ve ever had?
  11. 11
    If you were famous, what would you be famous for?
  12. 12
    What’s your favorite board game?
  13. 13
    What are you most afraid of?
  14. 14
    You can only pick one: love or money?
  15. 15
    What’s your worst nightmare?
  16. 16
    What would you do if you won the lottery?
  17. 17
    If you had 3 wishes, what would they be?
  18. 18
    When was the last time you laughed so hard you cried?
  19. 19
    If you were a superhero, what would your power be?
  20. 20
    Who’s your celebrity crush?
  21. 21
    What’s one food you can’t live without?
  22. 22
    Are you a homebody or an explorer?
  23. 23
    Have you ever gone skinny dipping?
  24. 24
    What’s your favorite tear-jerking moment in a movie?
  25. 25
    What’s your favorite book?
  26. 26
    What would you do if you won the lottery?
  27. 27
    What’s your ideal meal?
  28. 28
    What was the last show you binge-watched?
  29. 29
    What’s your go-to karaoke song?
    31. Advertisement
Section 3 of 6:

Romantic

PDF download Download Article
  2. 2
    What’s your idea of a perfect date?
  3. 3
    What does love mean to you?
  4. 4
    Do you prefer hugging or kissing?
  5. 5
    Do you prefer movie or restaurant dates?
  6. 6
    Do you believe in love at first sight?
  7. 7
    Where would you take someone on a first date?
  9. 9
    In your opinion, what’s the worst pickup line?
  10. 10
    What does your ideal relationship look like?
  11. 11
    Do you believe in soul mates?
  12. 12
    Would you rather go on a romantic getaway or Netflix and chill?
  13. 13
    When was your first kiss?
  14. 14
    Have you ever dreamed about me?
    16. Advertisement
Section 4 of 6:

Spicy

PDF download Download Article
  2. 2
    What’s your biggest turn-on?
  3. 3
    What’s one thing you’ve always wanted to try in the bedroom?
  4. 4
    What would you do if I answered the door naked?
  5. 5
    Lights on or off?
  6. 6
    Do you have a secret fantasy?
  8. 8
    What do you wear to bed?
  9. 9
    Do you think about me when you’re alone?
  10. 10
    Are you into giving or receiving?
  11. 11
    Do you like massages?
  12. 12
    Do you have a guilty pleasure?
    14. Advertisement
Section 5 of 6:

Deep

PDF download Download Article
  2. 2
    What traits do you think are the most important?
  3. 3
    Have you ever had your heart broken?
  4. 4
    What’s something you regret?
  5. 5
    What’s the nicest thing someone’s done for you?
  6. 6
    Who do you look up to?
  8. 8
    What do you admire most about your life?
  9. 9
    What’s an accomplishment you’re proud of?
  10. 10
    What’s your dream job?
  11. 11
    If you could change one thing about yourself, what would you change?
  12. 12
    What would you change about social media?
  13. 13
    What’s your biggest fear?
  14. 14
    What’s the best gift you’ve ever gotten?
  15. 15
    What makes you angry?
  17. 17
    How would your friends describe you?
  18. 18
    What’s your favorite childhood memory?
  19. 19
    Are you an introvert or an extrovert?
  20. 20
    What do you admire most in people?
  21. 21
    Do you believe in second chances?
  22. 22
    What are you the most grateful for?
  23. 23
    What’s the most spontaneous thing you’ve ever done?
    25. Advertisement
Section 6 of 6:

Silly

PDF download Download Article
  2. 2
    Would you rather share your internet search history or bank balance?
  3. 3
    If you came with a warning label, what would it say?
  4. 4
    Would you rather be a high school teacher or a clown?
  5. 5
    What’s the sexiest vegetable?
  6. 6
    If you were president, what would you do first?
  7. 7
    Would you rather only speak in rhyme or sing every time you speak?
  8. 8
    Is a hot dog a sandwich?
  9. 9
    What’s one sound that describes you?
  10. 10
    Would you rather be itchy all the time or have constant hiccups?
  11. 11
    If you were a ghost, what would you haunt?
    13. Advertisement

Expert Q&A

Ask a Question
200 characters left
Include your email address to get a message when this question is answered.
Submit
      Advertisement

      Tips

      Show More Tips
      Submit a Tip
      All tip submissions are carefully reviewed before being published
      Name
      Please provide your name and last initial
      Submit
      Thanks for submitting a tip for review!
      Advertisement

      You Might Also Like

      The Ultimate Collection of Funny, Cheesy, & Romantic Rizz Lines
      21 Questions Game: Spicy & Freaky Questions to Get to Know Your Crush
      100+ Flirty Things to Say to a Girl & Boost Her Self-Esteem
      20+ Signs a Guy is Attracted to You
      How to
      Seduce a Man
      140 Flirty Jokes & Pick-Up Lines to Make Her Laugh
      How to
      Seduce a Woman
      70+ Sweet, Playful & Steamy Good Morning Texts To Send Your Man
      3 Ways to Be Smooth and Rizz Up a Girl
      How to
      Seduce an Older Woman
      What Are the Biggest Turn-Ons for Guys?
      Reading Women’s Body Language: Signs & Signals That She’s Flirting
      How to
      Flirt
      How to
      Talk to a Girl
      Advertisement

      About This Article

      Thanks to all authors for creating a page that has been read 27,640 times.

      Did this article help you?

      Advertisement