190 Really flirty questions to ask a guy

If you’re looking to spice things up with the guy you like, here are 190 really flirty questions to ask a guy you want to pursue.

Whether it’s your first date or you have been seeing each other for some time, using the right questions helps gauge his personality and determine your compatibility.

Flirty Questions To Ask A Guy

1. What do you find most enjoyable about me?
2. Do you know how your smile affects me when we interact?
3. I’m sure we can come up with some fun ways to get to know each other better.
4. Wouldn’t it be fantastic if you could be why I smile daily?
5. What keeps you wanting to chat with me?
6. Can you make me laugh right now?
7. If you could be anyone for a day, who would it be and why?
8. What has been the greatest compliment you’ve ever received?
9. I would love some insight into your current thoughts.
10. Do you prefer texting or talking on the phone?
11. Would you instead go out for a date night or have an in-home cozy evening?
12. What’s one new hobby or interest that you are exploring?
13. Can you teach me something new?
14. How many licks does it take to reach the center of a Tootsie Pop?
15. Are there any experiences that have piqued your interest, yet you have not had a chance to explore them yet?
16. Do you have any helpful flirting advice to share?
17. What’s the most subtle way of showing someone that you’re interested?
18. Are you competitive, whether in games or real life?
19. What brings out the smile on your face and gives you that much-needed boost of energy?
20. What interests do we share?
21. We should have an in-depth conversation; what do you think?
22. What potential date ideas do you have in mind?
23. How can I get to know you even better?
24. What’s something overly cheesy that you secretly enjoy?
25. Are there some activities in life you find yourself trying to avoid, perhaps due to not liking them enough or fear of missing out on some exciting experiences? Are these things on your list of must-do’s?
26. Do you think it’s possible to fall in love with someone without ever meeting in person?
27. Are there any topics or skills on your mind that have been keeping you from learning more and keeping your curiosity burning strong?
28. Let’s play a game – truth or dare?
29. Do you believe in fate, or do you create your destiny?
30. Can you summarize everything I need to know about you in one sentence?
31. What do you find attractive about someone else?
32. What has been your most daring adventure?
33. Do you have any dating pet peeves?
34. What would you bring if we were on a deserted island together?
35. Is there a question that’s been on the tip of your tongue every time we talk, one that you’ve been meaning to ask me but haven’t quite found the right moment for?
36. How do you like to spend a lazy Sunday with no plans?
37. Do you believe there’s an ethical difference between flirting and being friendly?
38. Is there something you’ve been yearning to do for that special someone in your life, a romantic gesture or thoughtful act you’ve wanted to carry out?
39. What’s the most thoughtful gift you’ve ever given someone?
40. Do you have any favorite quotes or mantras that guide your daily life?
41. Do you have some ideas on how to make someone feel truly special?
42. And finally, what can’t wait until tomorrow morning when the memories will last forever?
43. Do you believe in the possibility of having an intimate friendship with someone you’re attracted to?
44. What’s your favorite physical feature on someone?
45. What would be a creative way to ask someone standing near you out?
46. Do you believe in love at first sight?
47. What sexual experience would be ideal for you?
48. What’s the sweetest thing someone has ever done for you?
49. Let’s play 20 questions – you ask one, then I’ll ask one.
50. If you could go back in time and give yourself one piece of dating advice, what would it be?

Questions To Ask Your Boyfriend That Are Cute And Flirty

1. Do you mind if I use your shirt as a pillow?
2. How do you always look so great?
3. What was the best text message you’ve ever received from me?
4. Do you think I’m cute?
5. What three things would you bring if we were stranded on an island together?
6. How often do you think about me when we’re apart?
7. Is there something on your mind that you’ve always wanted to ask me but haven’t yet?
8. Do you mind if I hold your hand right now?
9. Where would you take me if you could choose anywhere in the world to explore?
10. What was our deepest conversation ever?
11. Do you have any great flirting tips for me?
12. What’s your favorite thing about me?
13. What would you wish I knew more about you?
14. Could you show me how to be an amazing kisser?
15. What activity would you suggest we try together?
16. Do you enjoy it when I show affectionate affection towards you in public?
17. Could you teach me how to cook your favorite meal?
18. What’s the craziest thing you’ve ever done for love?
19. What have you always wanted to try in the bedroom?
20. Do these questions bother you?
21. Describe the moment when you knew you were in love with me?
22. What’s your favorite memory of us together?
23. Would you rather keep quiet or teach me how to play your favorite video game?
24. What would make for the perfect date night for both of us?
25. Do you mind if I keep a secret from you?
26. What would your superpower be, if any?
27. How does it feel when you’re with me?
28. What has been the most romantic thing you’ve ever done for someone else?
29. Do you have any flirting advice that I may not have heard before?
30. What surprises you most about me?
31. What could you sum up our relationship in three words?
32. Demonstrate something that you’re particularly adept at doing for me.
33. What’s your biggest turn-on?
34. What do you enjoy most about cuddling with me?
35. Who do you wish would join us on our date if there was one celebrity you could invite?
36. Can you share with me a recent dream you had?
37. What’s something that makes you wish for more time with me?
38. How do you feel when I smile at you?
39. What’s the most embarrassing thing that’s ever happened to you on a date?
40. Can you give me some tips for dealing with challenging situations at work/school?
41. What’s your favorite thing about me physically?
42. What would it be if we could choose any activity together right now?
43. How does it feel knowing I’m thinking of you?
44. Share something unique that only you know about you.
45. What keeps bringing back memories of me?
46. Could you teach me how to dance along to your favorite song?
47. What do you find challenging about asking these questions?
48. Are there any topics that make you nervous?
49. How would you describe your relationship with me in one sentence?

Flirty Questions To Ask A Guy To Know A Guy Deeper

1. What is your biggest turn-on?
2. What qualities do you look for in a girlfriend?
3. Have you ever been in love before?
4. What would be an ideal date?
5. What is the sexiest thing a girl can do to turn you on?
6. What romantic gesture have you ever performed for someone?
7. How do you like to be touched?
8. What adventurous act have you ever performed in the bedroom?
9. What is your wildest sexual fantasy?
10. What do you consider an essential aspect of any relationship to you?
11. Have your feelings ever been hurt in public?
12. Which part of a woman’s body do you find most beautiful?
13. Where would you want to go on an ideal romantic getaway, and how do you like being pursued?
14. What is your biggest fear when it comes to relationships?
15. Have you ever had a one-night stand?
16. What was the best compliment you ever received from a girl?
17. How would you describe an ideal kiss to someone special?
18. What is the most embarrassing thing that has ever happened to you on a date?
19. What do you enjoy doing in your free moments?
20. What would be your dream job if it existed?
21. Do you feel comfortable taking risks?
22. And finally, what’s your favorite pastime while lying in bed?
23. What is the most important lesson you have learned from a past relationship?
24. Do you believe in love at first sight?
25. What would make for the perfect relationship for you?
26. What has been the best thing that any woman has ever done for you?
27. Do you believe in fate?
28. What’s an ideal morning for you?
29. How do you feel about being friends with an ex?
30. What is your biggest goal in life?
31. What is the most romantic thing you have ever said to someone?
32. What is currently important in your life?
33. How important communication in a relationship is?
34. What has been your most adventurous act?
35. What is the most valuable lesson you have learned in life?
36. How do you feel about commitment?
37. What’s an ideal wedding day?
38. What’s your ideal self-image?
39. What do you find most admirable about yourself?
40. How would you prefer being approached by a girl?
41. What is the most romantic thing a girl has ever said to you?
42. What would you consider an ideal evening for you?
43. What do you like doing to unwind after a long day?
44. What activity do you like doing on weekends?
45. How do you feel about being vulnerable in a relationship?
46. What would be the perfect proposal to you?
47. What’s your favorite way of showing affection?
48. What qualities are most important when searching for the right partner?
49. What is the most essential act you have ever performed for someone you cherish?

Flirty Questions To Ask A Guy You Just Met

1. What are your hobbies, and do they include spending time with me?
2. I’d love to know your music preferences; do we like the same songs?
3. Where did you see your last concert, and could we go to one together?
4. Is dancing something you’re into? It would be fun to dance with you.
5. Tell me your favorite drink so I can have it ready next time we hang out.
6. For a first date, what’s an activity that would help us get to know each other?
7. Do you think people can fall in love at first sight, or was it just my feeling?
8. What’s the perfect date for both of us? Are you into cooking, by any chance?
9. Your favorite food is? Maybe I can make it for you one day.
10. Do you have a favorite book? Let’s read it and discuss it!
11. Traveling – is it something you enjoy? We could travel together sometime.
12. What’s the most exciting place you’ve been to? I want to join you there next time!
13. Got any pets? I’m also an animal lover.
14. What TV show do you binge-watch sometimes? Maybe we should watch it together!
15. Do you have siblings? They must be cute, but not as much as you!
16. I’d like to hear about your hobbies. Perhaps I can participate too?
17. Exercise – is that something you enjoy? I’d like to be your workout partner.
18. Tell me about your favorite sport. Playing it together would be fun!
19. Got any hidden talents? I’m excited to find out what they are.
20. Your craziest adventure sounds interesting. I hope I can be a part of your next one!
21. What’s the best prank you ever played – and please tell me it wasn’t on me!
22. Do you prefer going out or kicking back at home? We should do both!
23. How would the ideal weekend with me look to you?
24. Bucket lists, do you have one? Spending time with you is on mine.
25. The most spontaneous thing you’ve done… Was it asking for a date by any chance?
26. Narratives of fate: believe in them? Like destiny brought us here?
27. Your ideal way to unwind after work? I hope it involves hanging out with me.
28. Someone’s romantic gesture that touched your heart – tell me, so I can up the game.
29. Do surprises bring you joy? ‘Cause I’ve got a surprise planned.
30. You have a fave season? Mine might just be the season of love…
31. Dream jobs, if possible, what would yours look like?
32. Whats the weirdest food that’s ever entered your mouth. Should we give it a try together?
33. You into parties? Let’s party up some time!
34. What trait about yourself do you love most – is it your stunning smile?
35. If you’ve got a pickup line ready, I’m here waiting to hear it.
36. The nicest compliment you’ve received – I want to say something even nicer.
37. Show me your favorite dessert, and I’ll bake it for us.
38. Tell me about the perfect day spent with me. What would we do?
39. Cool, show ‘em off the next time we’re together!
40. Your absolute fav color – let me know, and I’ll wear it next time we meet.
41. Love taking them? We should snap some cute shots together.
42. Cuddling fan? ‘Cause I might enjoy cuddling with you someday.

Kary Walters

I’m Kary Walters, a wedding planner, life coach, and writer with a passion for helping couples stay together and achieve their relationship goals. With over a decade of experience, I specialize in self-improvement and have worked with individuals & couples facing challenges.