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44 Flirty Questions - Amazing List To Make Your Way To His Heart

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Robin is our female dating expert, style guru and resident life coach. Her expertise has been featured on Reader's Digest, Bustle, Hello Giggles, Best Life Online, Cheat Sheet, and many more. She lives with her fian ...
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by | | August 11, 2021


If you're looking for flirty questions, this is the place.

We've done successful blogs on how to tell a guy you like him and questions to ask a guy, so you trust us here, girl.

We will give you the only flirty questions needed to start a conversation and get his heart along the way.

Warning: these flirty questions are bold, so see if your crush can keep up.

Let's start!

Contents

13 Best Provocative Questions To Tease Him

Some people are natural-born flirters. Others, not so much. If you're socially awkward, flirting can be the hardest thing ever. Having a set of the flirtiest questions at hand can make the process a lot easier. Today, we've rounded up a bevy of flirty questions to impress the man of your desire.

Here are the 13 best flirty questions to tease him

1. What kind of a boyfriend would you be?

You want to know what kind of boyfriend you'll be getting. There's no telling if it will be the perfect relationship, but it's a great question to start.

2. What was your first impression of me?

Get to know what part of you appealed to him. This is a good flirty question for a drinking game between the two of you.

3. How would you describe your ideal relationship?

Learn what they expect from you if your relationship blossoms into something more. It's the perfect flirty question to set up some expectations (and so you know what to do!).

4. What's one thing you're super passionate about?

You get to learn about what they care about in their life. It's an interesting question because it's always great to see someone talk about what they're passionate about in life.

5. Do you have a secret fantasy, and if so, what is it?

This is bound to raise eyebrows... in a fun way. It's not exactly one of the dirty questions because it can be a funny question.

6. Why don't you tell me more about yourself?

This is a chance to discover things about him that you didn't know. It's simple, but it's the right question to learn more about them in one go.

7. Do you ever get shy around me?

Men act differently if they're around a girl they like. If they get shy around you, then they probably like you a lot. That's your sign to make a move, girl.

8. What's your favorite thing to do on a date?

It's a fun question because it's a great way to know what to do for him on his birthday. Or you know, for when you're going out on a date... once you're his girlfriend.

9. What makes you laugh?

Find out if they have a sense of humor. Or if their humor's the weirdest thing ever. Then add that to your agenda to catch him.

10. What do your weekends look like, and how do I fit into them?

This one's a shoot-straight from the hip message. Your crush will like it. It sounds like the craziest thing to be upfront, but it works!

11. What is something about you that would surprise me?

People often have amusing quirks. Girl, you might be shocked to hear what's his when you ask flirty questions like this.

12. What's your idea of a perfect date?

Is it a relaxing afternoon at the beach with packed lunch? Whatever it is, it should set the mood for a perfect kiss.

13. What emoji do you usually use when you're flirting?

This is one of the cute questions a girl could ask a guy. It's bound to be fun. Everyone has a favorite emoji.

12 Playful Questions To Ask A Guy You Like

You don't want to ruin the chances of hitting it off with someone you like. However, it's often tricky to impress someone you don't know, especially on the first meet. You haven't a clue what they want and the things that put them off. Even then, you can still put a smile on their face with these flirty questions to ask a guy you like.

Here are the 12 flirty questions to ask a guy you like:

14. Are you drawn to brains or beauty?

He better say both, just because he's with you. Remember to ask him why. Girl, you'll definitely be flattered.

15. If you won a trip to go anywhere on earth, where would you take me?

This is a great way to learn about his dream destination and favorite place. Make sure to share yours as well. You may have a lot in common.

16. Have you ever made a romantic gesture?

Flirty questions like this will show you if he's a hopeless romantic. Or if he is more of the casual relationship kind of person.

17. What is your love language?

There are 5 love languages. Where does he fall? It's important to know this informative and flirty question.

18. What's your favorite love song?

You'll understand his taste in music. Hopefully, he has good taste. Make sure to ask this one in your questions game, girl.

19. What's the perfect way to ask someone out?

This is the perfect question to ask if you want to find out just how romantic he is.  Try to add some other follow-up flirty questions to snatch that date with him.

20. Are you aware of how amazing you are?

This takes the cake for flirting questions. This will leave him blushing for you, girl.

21. What song would you compare our relationship to?

This is such a good question because it is always an interesting one. You could end up with a whole playlist.

22. What are you doing for the rest of your life?

Does he have room for you? This can easily be one of those deep questions that tell you a lot about him.

23. What does your future look like?

What are his plans for the future, and are you in them? Does he see a vivid image of his life with you 5 or 10 years from now? This question will show you.

24. How many million times do you think about me when I'm away?

The more he thinks about you, the more attracted he is to you. Watch out for his answer to this question.

25. What are your biggest passions right now?

Find out what drives him. It's one of those personal questions that you should know about him.

9 Cheeky Questions To Ask A Guy Through Text

So, you have a new crush. It's an exciting time for a girl filled with awkward moments and late-night texting, and tons of flirting. You're at the stage when you're getting to know each other. It feels unreal. But it's also nerve-racking to feel each other out and explore your connection. Use our collection of questions to ask a guy over text to get your crush blushing for a girl like you.

Here are 9 questions to ask over text:

26. If you could come to my dream tonight, what would you do?

Allow him to express his deepest desires in a flirty text. You never know; this might be a sexy question.

27. Where do you want to be right now?

This one is similar to asking, "If you could be anywhere, where would you be? And will you take me with you?" If he were not where he is, would he be with you at some dream destination?

28. What would you do to me If I'm with you right now?

It sounds like one of those naughty questions, but it can feel good to hear the answer. This will get him thinking about you.

29. Who was the last person you tried to impress?

People want to impress those they admire. So the answer should better be you, but someone else isn't the worst thing.

30. How do you make small talk with a stranger?

The art of making small talk is rare. This random question can give you an idea of how you should do it, too.

31. Does being sneaky give you a thrill?

Maybe it does, but, girl, you shouldn't be dating a sneaky man. We can learn from a past relationship.

32. Do you think you'd enjoy a love-hate relationship?

Does he enjoy being in a relationship full of drama and upheaval followed by momentary peace?

33. So what do you think we should do this weekend?

Grab this opportunity to ask him out instead of waiting for him to ask you. You got this one in the bag, girl!

34. What's something that will make me fall in love with you instantly?

What does he think is the most admirable trait is? Is it his physique? His charms? His humor? Hear his answer and tell him what you really think.

10 Would You Rather Questions To Charm Him

Would you rather questions are a fun and easy way to woo your crush. You get to break the ice and know your date better. The game is simple; take turns asking each other would you rather questions with two different options. Spice things up by asking him why he chose that answer.

Here are 10 flirty would you rather questions:

35. Would you rather hug or kiss?

Some men would rather hug their partners than kiss them. It's essential to know. This is one of the best romantic questions.

36. Would you rather kiss on the first date or wait until you know her/him better?

This is your chance if he kisses a girl as soon as the first date. Does he value creating an emotional connection more than a physical one?

37. Would you rather write a love letter or get a love letter?

Love letters never go out of fashion. If he chooses the first one, what would he write for a lovely girl like you?

38. Would you rather stare into your partner's eyes or stare at your partner's lips?

Find out what features they find attractive in women. And why not turn this into one of those dare questions?

39. Would you rather have pillow fights on the bed or wrestle one another on the bed?

Explore his fun and childish side. Being playful is a big part of a romantic relationship.

40. Would you rather have a fling with your high school crush or with your celebrity crush?

Everyone has a celebrity crush and a high school crush, even you. Between a girl and a dude, it's fun to reminisce about your past obsession.

41. Would you rather be known as someone who dresses to kill or be known as a smooth talker?

Do they go for the look or the personality when being noticed by a girl? Don't forget to ask about the reasons.

42. Would you rather sing your heart out to your partner in private or in public?

Either way, it must be true love to sing for someone. Is he into public displays of affection? Now you know how to surprise him on his birthday.

43. Would you rather shower your partner with gifts or shower your partner with money?

What's his love language when it comes to gifting? What would he shower the girl of his dreams?

44. Would you rather give your partner a back rub or give your partner a foot rub?

Both are pretty good. Think about all the romantic moments you'll spend together giving each other back rubs or foot rubs.

Downloadable and Printable List of Questions That Are Flirty

Here is a downloadable and printable jpg/pdf list of flirty questions (right-click the image and select Save Image As...):

Frequently Asked Questions

Asking flirty questions can be challenging for some people. Regardless, we'll answer the most asked questions about getting flirty with a man you like.

How do you flirt with a guy with words?

Guys are direct. Believe it or not, some men don't even notice that girls are flirting with them. So, muster up your confidence by directly telling them your intention. As for the flirting stuff, try to show your admiration by telling them what you like and appreciate about them. Also, you have our list of flirty questions to use as reference.

What should I do to win his heart through chats?

Online dating is a crucial part of dating. You can win his heart with some patience and dedication in your messaging. Ask him about his day. Ask about his favorite things. The more you show interest in him in your chats, the more chances that you'll win him over.

Is asking questions that are undeniably flirty enough to win him?

Flirty questions are one thing, but showing your man what you feel about him is the key to getting in a relationship with him. Again, be direct in your words and actions.

How do you tell if a man is also interested in you?

What do you do when you're interested in someone? You ask tons of questions. You find ways to be with him. You find reasons to talk to him. You want to find out more about him. So if he does the same thing for you, then you're set.

What should I do to make him want me?

When you're constantly texting or meeting with a guy, chances are he becomes attached to you. So try to hold back on your affection for a day or two. See if he notices and finds a way to be with you. It might be ironic, but giving him space can make him want you more.

How To Pick The Best Flirty Questions

You've been wondering how to make him want you, right? Well, we've got some good news for you.

It's tempting to choose flirty questions at random and throw them at whoever tickles your fancy. Don't. Instead, put some thought into selecting the best questions. This way, you have a better chance of having a positive impact.

Here is how to pick the best questions:

1. Consider His Personality

As you flirt with men, you'll realize those different personalities will respond differently to various flirting approaches. For this reason, you want to choose your questions clearly after assessing his personality type.

Some respond better to a daring, serious approach, while others prefer a funny one.

2. Confidence is Key

Confidence is attractive. It will help if you deliver messages with confidence. Take a deep breath and go for it; he'll appreciate it. Men like a girl with guts. The most important thing is to remember to be yourself.

3. Get the Timing Right

You need to deliver the lines at the right time. The feeling and the vibe have to be correct. Often, you'll have a hunch when the right moment comes.

More Great Ways to Talk to Guys

Sure, a smile, eye contact, and some confidence will go a long way when you're trying to talk to men. But these are only the surface ingredients. Sometimes, you need a little help to get things going. To get you off to the races, here are some tips for talking to men.

  1. Looking to find out more about someone you just met? Here are some casual questions to get to know someone.
  2. Here are some sexy questions to ask your boyfriend. They're suitable for a date or a casual hangout at home.
  3. You can't go wrong with our collection of interesting questions to ask a guy.

In Conclusion

Flirting can be considered an art that takes time to hone and perfect. However, you don't have to be the best to win over someone you've been eyeing. These questions to ask a guy can come in handy in pretty much any situation. They're also a great fallback if you're wondering how to tell a guy you like him. Don't wait too long. Go out and put a smile on someone's face today. Fortune favors the brave.

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