Cute, Fun, & Romantic Questions to Ask a Guy

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

Written by Suzanna Mathews | Edited by Aly Rusciano

Last Updated: May 21, 2023

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• Cute
|
• Fun
|
• Romantic
|
• Spicy
|
• Deep
|
• Silly
|
• Tips

|Show more |Show less

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.

Steps

Section 1 of 6:

Cute

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1. 
   1
   What color do you think I look best in?
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?
11. 
    11
    What are 3 things on your bucket list?
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?
21. 
    21
    What’s your favorite thing about me?
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Section 2 of 6:

Fun

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1. 
   1
   What’s a song that describes us?
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?
30. 
    30
    Do you think aliens exist?
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Section 3 of 6:

Romantic

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1. 
   1
   What’s your love language?
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?
8. 
   8
   Would you consider yourself a romantic?
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?
15. 
    15
    Do you think I’m a good kisser?
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Section 4 of 6:

Spicy

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1. 
   1
   How do you picture me at night?
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?
7. 
   7
   What are your 3 favorite body parts?
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?
13. 
    13
    Are you a big spoon or a little spoon?
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Section 5 of 6:

Deep

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1. 
   1
   What does success look like to you?
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?
7. 
   7
   Have you ever been in love?
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?
16. 
    16
    If you could go back in time and change one thing, what would you change?
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?
24. 
    24
    What’s the biggest lesson you’ve learned?
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Section 6 of 6:

Silly

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1. 
   1
   What meme best describes your life?
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?
12. 
    12
    What alias would you use if you were a spy?
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Tips

• The best way to flirt with a guy is to be playful and have fun! So, don’t be afraid to tell a few flirtatious jokes to make him smile.
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• Ask about a guy’s interests and passions to see what you have in common and spark a deeper conversation.
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• Use these questions as conversation starters in person or over text—they work just the same!
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