Cute, Fun, & Romantic Questions to Ask a Guy

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Conversation starters to spice things up and get to know him better
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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

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  2. 2
    What’s your favorite part of the day?
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  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?
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Section 2 of 6:

Fun

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  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?
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Section 3 of 6:

Romantic

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  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?
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Section 4 of 6:

Spicy

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  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?
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Section 5 of 6:

Deep

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  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?
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Section 6 of 6:

Silly

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  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?
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Join the Discussion...

What are some flirty questions to ask a guy?
WikiLynxJumper585
WikiLynxJumper585
Please give me your favorite flirty questions to actually get a guy hooked. I’ve got a few guys I’m talking to, but I feel like I’m always struggling to keep the conversation going in a way that doesn’t sound like I’m talking to my parents. I’m just not naturally “sexy” I guess when it comes to texting or chatting. So yeah, lay your best lines on me! The more the better!
WikiCheetahTamer353
WikiCheetahTamer353
Ooo okay, I love this game. It’s so fun finding those little curious, testy lines that feel like they’re just one-degree away from being full-blown flirty. I spent a few minutes crafting my favorite lines, so feel free to borrow anything I’ve got here!

“If you could plan the perfect first date, what would it be?”
“What's your idea of the perfect lazy Sunday?”
“What's something you're passionate about that most people don't know?”
“Which childhood cartoon character did you have crush on growing up?”
“What kind of trouble did you get into as a kid?”
“If you had the whole city to yourself for a day, where would you go?”
“What’s your guilty pleasure?”
“What’s the best compliment you’ve ever received?”
“How would you describe your style?”
“Are you a boxers or a briefs guy?”
“What’s your absolute favorite way to be surprised?”
“What's the most sensual food in your opinion?”
“What's the perfect soundtrack for a romantic evening?”
“What's your ideal morning-after breakfast?”
“What’s the best place you’ve ever been on a date?”
“If you had to seduce someone using only words, what would you say?”
WikiAxolotlWatcher104
WikiAxolotlWatcher104
The way that you deliver questions can have a huge impact on whether they come across as flirty! Think about your body language and your tone of voice. If you lean into him and make eye contact, or smirk, or play with your hair, or touch his arm, these can all heighten the flirtiness factor. Just make sure not to go overboard or it can just sound like a sexual innuendo. I know it's easier said than done to strike a balance between getting to know someone in a flirtatious manner and laying it on too thick.
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      References

      1. ↑ Suzanna Mathews. Dating & Relationship Coach. Expert Interview
      2. ↑ Suzanna Mathews. Dating & Relationship Coach. Expert Interview
      3. ↑ Suzanna Mathews. Dating & Relationship Coach. Expert Interview
      4. ↑ Erika Kaplan. Relationship Advisor. Expert Interview
      5. ↑ Cher Gopman. Dating Coach. Expert Interview
      6. ↑ Cher Gopman. Dating Coach. Expert Interview

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