100 Flirty Questions to Ask a Guy

100 flirty questions to ask a guy

Are you trying to make a connection with a special guy but don’t know where to start? Flirting is an art form, and the key to getting it right is asking the right questions. We’ve come up with 100 flirty questions to ask a guy that are sure to get the conversation going and help you make a lasting impression.

Whether you are looking for a subtle way to show your affection or just want some fun ideas for spicing things up, these flirty questions will help guide your dialogue toward making an unforgettable connection between both of you. We look at yes or no questions, open-ended questions, would you rather questions, and dirty flirty questions. So, let’s dive into the world of flirty questions to ask a guy.

20 flirty yes or no questions to ask a guy

1. Have you ever had a crush on someone you shouldn’t have?

2. Do you believe in love at first sight?

3. Have you ever had a secret admirer?

4. Do you enjoy neck kisses?

5. Have you ever sent a risky text to someone?

6. Have you ever been in love before?

7. Do you believe in soulmates?

20 flirty yes or no questions

8. Would you ever make the first move on someone you really liked?

9. Have you ever had a dream about me?

10. Are you usually the one to initiate conversations with someone you like?

11. Do you like it when a girl makes the first move?

12. Have you ever been in a long-distance relationship?

13. Do you believe in fate bringing two people together?

14. Have you ever had a crush on someone you never expected to?

15. Do you think about me when we’re not together?

16. Do you enjoy flirting with me?

17. Would you like to go on a spontaneous adventure with me?

18. Can you imagine us as a couple?

19. Do you think we have chemistry?

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

These flirty yes or no questions for a guy are a quick and easy way to break the ice with him and get to know them a little better. They are also great for sparking flirty conversations and finding out if there is a potential connection between you and the person you’re interested in.

20 ‘get to know you’ flirty questions to ask a guy

1. What’s your idea of the perfect date?

2. How would you describe your flirting style?

3. What’s the most adventurous thing you’ve ever done?

4. What three things would you bring if we were stranded on a deserted island together?

5. What’s the most spontaneous thing you’ve ever done for someone you liked?

6. What’s your go-to move when you’re trying to catch someone’s attention?

7. If you could only use one word to describe me, what would it be?

8. What’s the most attractive quality you look for in a person?

9. What’s your favorite physical feature about yourself?

10. What’s your favorite physical feature about me?

11. If you had to serenade me, what song would you choose?

12. Are you a good kisser?

13. What’s the naughtiest dream you’ve had about me?

14. What’s the most memorable compliment you’ve received?

20 'get to know you' flirty questions for a guy

15. How would you spend a lazy Sunday with me?

16. How would you describe your perfect kiss?

17. If you could have any superpower to impress someone, what would it be?

18. What’s the most romantic thing you’ve done for someone?

19. If you could be any fictional character’s love interest, who would it be?

20. What’s the hottest thing someone has ever said to you?

These flirty get-to-know-you questions to ask a guy are great for building a deeper connection with him and finding out what sparks their interest. They also provide insight into their personality and give you the opportunity to show your own interests and flirtatious side.

20 flirty ‘would you rather’ questions to ask a guy:

1. Would you rather be kissed on the lips or on the neck?

2. Would you rather receive a sweet goodnight text or a surprise morning kiss?

3. Would you rather have a candlelit dinner at home or a romantic picnic under the stars?

4. Would you rather have a shower together or a bath?

5. Would you rather go on a spontaneous weekend getaway or have a cozy movie night at home?

6. Would you rather have a slow dance in the rain or a passionate kiss in front of a breathtaking view?

7. Would you rather I bring you breakfast in bed or cook a delicious brunch together?

20 flirty 'would you rather' questions for a guy

8. Would you rather have a playful pillow fight or a tickle war?

9. Would you rather have a date night at a fancy restaurant or a fun night out dancing?

10. Would you rather cuddle up by a fireplace or have a romantic walk on the beach?

11. Would you rather receive a cute good morning selfie or a flirty voice message?

12. Would you rather have a surprise date planned for you or plan a surprise date for someone special?

13. Would you rather wake up next to someone special or go to sleep next to them?

14. Would you rather Netflix and chill or go out for a romantic date night?

15. Would you rather receive a passionate kiss or a sensual massage?

16. Would you rather have a candlelit bubble bath or a hot tub date?

17. Would you rather go skinny dipping at night or have a steamy makeout session in the rain?

18. Would you rather have slow and sensual sex or quick and passionate sex?

19. Would you rather receive a surprise gift or be surprised with a home-cooked meal?

20. Would you rather receive a flirty text or a sexy photo from me?

This is a fun and flirty game that can turn up the heat between two people. These questions are perfect for sparking playful banter and discovering what your crush prefers in different romantic scenarios. Who knows, you might even get some inspiration for future dates or surprises.

20 dirty and flirty questions to ask a guy

1. What’s your biggest turn-on?

2. What’s your favorite position?

3. What’s your favorite thing to do in the bedroom?

4. What’s one of your secret kinks?

5. Are you more dominant or submissive in bed?

6. What’s the most daring place you’ve ever had sex?

7. What’s your favorite type of lingerie on a woman?

8. What’s your opinion on BDSM? Have you ever tried it?

9. Have you ever had a one-night stand with someone you knew?

10. Do you like using toys during sex? If so, which one is your favorite?

11. Have you ever been caught in a compromising position?

12. Would you rather give or receive massages with happy endings?

13. Do you like dirty talk?

14. Have you ever tried role-playing in bed?

20 dirty and flirty questions for a guy

15. What’s the naughtiest thing you’ve ever done?

16. Do you prefer giving or receiving?

17. Have you ever used food during foreplay?

18. Do you prefer slow and sensual or rough and wild?

19. What’s the sexiest piece of clothing someone has ever worn for you?

20. How adventurous are you when it comes to exploring different positions?

These dirty and flirty questions to ask a guy are perfect for turning up the heat and getting to know his wild and naughty side. Just make sure that you’re both comfortable with discussing these topics and always practice safe and consensual sex. Remember, communication is key in any romantic or sexual relationship. So have fun, but also be respectful of each other’s boundaries.

20 questions to deepen the connection with a guy

1. What’s your biggest fear?

2. What’s the most important value to you in a relationship?

3. Do you believe communication is key in a relationship? Why or why not?

4. Have you ever been heartbroken before?

5. How did your last relationship end?

6. What are your top three values and why are they important to you?

7. What is something you’re passionate about, and why does it bring you joy?

20 questions to deepen the connection with a guy

8. Can you share a moment when you felt vulnerable and how it affected you?

9. What’s something you’re passionate about that others may not know about?

10. If money wasn’t a factor, what would be your dream job?

11. How do you show someone you care about them?

12. What’s your love language?

13. Do you have any regrets in life?

14. What’s one thing you’ve always wanted to try but haven’t yet?

15. Are you close with your family?

16. How do you cope with difficult situations?

17. What are your goals and ambitions for the future?

18. Do you believe in second chances?

19. What’s the most meaningful thing someone has ever done for you?

20. Are there any fears or insecurities that you’ve overcome, and how did you do it?

Once you’ve built a flirty and fun connection with a guy, it’s important to also deepen the emotional connection. These questions are great for getting to know him on a deeper level and understanding their values, fears, and aspirations. It shows that you’re genuinely interested in them as a person and not just their physical attributes. So, take the time to ask these questions and listen attentively to their answers. Who knows, it might just lead to a deeper and more meaningful connection.

When to use these questions

When it comes to asking flirty questions to a guy, timing is key. It’s important to choose the right moment to ensure the conversation flows naturally and both parties feel comfortable. One ideal time to ask flirty questions is when you’ve established a connection with the guy. Building rapport and establishing a level of comfort and trust sets the stage for more intimate conversations.

During a lighthearted conversation, such as discussing interests or engaging in playful banter, you can introduce flirty questions. This creates excitement and keeps the conversation interesting. Another suitable time is when there’s mutual interest. If you sense that the guy is reciprocating your flirting and showing signs of interest, it indicates he is open to deeper conversations and will likely respond positively.

Additionally, feeling confident plays a crucial role in asking flirty questions. When you’re at ease and confident in yourself, it reflects in your approach and makes the conversation more enjoyable for both parties. It’s important to gauge the guy’s reactions and responses; if he seems uncomfortable or uninterested, switching gears and steering the conversation in a different direction is best.

When to use these questions

These flirty questions to ask a guy can be used in various scenarios, depending on your intimacy level with the person. If you’re already in a committed relationship, these questions can still be used to spice things up and continue discovering new things about each other. Use them in person, over text, or even on a virtual date. Just remember to always keep the conversation respectful and consensual. Flirting should be fun and playful, not pushy or uncomfortable for either party. So use these questions wisely and have fun!

Final thoughts

In conclusion, the art of question-asking is an essential tool in building various types of relationships. These 100 flirty questions to ask a guy are just some examples to get you started but don’t be afraid to come up with your own and tailor them to fit the conversation.

Whether it’s adding a little spice with flirty and naughty inquiries, creating a fun and playful atmosphere with ‘would you rather’ scenarios, or getting to know his naughty side with dirty questions – there’s no denying the power of a flirty question. Just remember to always be respectful and aware of boundaries, communicate openly and honestly, and have fun getting to know this special guy on a deeper level. So go ahead, ask away! And who knows, you might just discover something new about yourself along the way.

If you enjoyed this post, you might also like 151 deep questions to ask to strengthen any bond or 60 couple questions to get to know your partner.

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