The Ultimate Guide to Asking Her the Right Flirty Questions at the Right Moment

Flirty Questions to Ask a Girl

Is there a girl that you are crushing on and you want to get closer but do not know how? Well, one way of doing that is by asking her some playful and flirty questions to start a spark or reduce any awkward tension. However, you should be aware that not all flirty questions are appropriate and you should also only ask them at the right time.

It is not uncommon for men to draw a blank when it comes to asking playful questions to a girl – especially one that they like. Therefore, we have created a comprehensive guide with a list of questions for you to ask her to begin a fun, light-hearted conversation that could eventually lead to something more profound which could strengthen your relationship. We have sorted the questions into different types so that you know which ones to ask according to how close your relationship with her is.

Flirty Questions to Ask a Girl

Coming up with a list of questions to ask the girl you are crushing on is not going to cut it. You will need to know which are the right questions to ask when the time is right. If you ask something too trivial, she might dismiss your question or even become bored. On the other hand, asking her something too intimate at the wrong time or when your relationship with her is not ready yet could potentially create tension or worse, offend her!

However, it really is not as difficult as you might think. We have broken down the fundamentals of asking the right flirty questions to the girl you like into three parts. After you have read our guide, you can immediately put the lessons learned into action and start getting the heart of the girl you desire!

Lesson 1: Find Out How She Would Respond In A Given Situation

When you haven’t yet established a deep bond with her and do not know much about her past, the best way is to ask hypothetical questions. This way, not only will you avoid offending her without meaning to, but you could also keep her imagination running – which is always a good thing! When a person’s creative juices are flowing, they tend to feel more relaxed and let their guards down, allowing you to get a peek into who they really are inside. These questions are a great way to get to know her better while averting any possible offensive topics to her. Remember, keep it light and humorous at this point because you do not want to hit her with the heavy stuff and scare her away.

  • If you found a pair of glasses that could see through clothes, will you use it?

This is definitely a fun question that is also a bit naughty. If the mood is right and she has been responding well to your advances, this question could turn up the heat and steer her in the right direction!

  • If you can instantly gain a new skill, which one will you choose?

Whatever her answer is, you should always follow up with a “why” if she does not elaborate on it. From here, you will be able to find out which skill she lacks but wants to gain. Better yet, if you happen to possess the skill that she wants to learn, you can teach her!

  • Say you found a lamp on the shore of the deserted island and a genie appears after you have rubbed the lamp. The genie grants you three wishes – what are they?

This is a fun way of asking what are the three things she wants most in life. Therefore, her answers will inform you of her values and what are the most important things to her. Will she be wishing for world peace or riches beyond her imagination?

  • Have you ever gotten out of your comfort zone before?

Of course, if she answers “yes”, then you should follow up with a question asking her to describe what she did. If she answers “no”, you could encourage her to try something exciting that she has never done before with you. That will certainly leave a strong impression on her.

  • If your house was on fire and you could only save one thing from being destroyed, what would it be?

A question that could tell you what is the one thing that she values most in her home. Prompt her to elaborate on why she wants to save that thing over others and her answer will be a valuable inspiration on what gifts you could give her in the future.

More:99 Fun Long Distance Birthday Gift Ideas to Make Anyone Smile!

  • Who would you like to have coffee with if you could meet anyone – dead, alive, or imaginary?

A fun way to find out whom she looks up to the most or has unresolved issues with. You could also share your own answer with her and both of you will end up knowing each other a bit more.

  • Would you agree to go with some friendly aliens who came to Earth and offered you a visit to their planet?

This is an entertaining and relatively “safe” question to ask when you still do not know each other that well yet. You could end up having a very entertaining conversation and have loads of fun with this one.

  • Should you discover now that you had only one more year to live, what changes would you make to your current life?

This could be a bit of a sensitive question to ensure that you only ask it when the moment is right or you would like to steer the conversation toward a more serious topic. This question will help you get to know the girl at a more profound level and find out how happy is she with her current life.

  • If you are going to get a tattoo, what would it be and where on your body would you have it?

This is a great way to find out if she already has a tattoo hidden somewhere on her body. If you are bold enough, you could even ask her to show you! It is also cool if she does not have a tattoo and you can offer to hold her hand if she ever decided to get one.

  • Which skill that you do not have which would you like to gain now?

This is a great way to find out what weaknesses she has but want to improve on without putting her in an awkward position. Follow up the question with why she wants to gain this skill and if you actually possess the skill she desires, then offer to teach her!

  • If you were stranded on a deserted island, what will be the three things you wish you had with you?

This question opens the doors to many possible answers and you could find out what her character is from her answers. Is she the practical and level-headed kind who will want a survival kit with her? Or is she the dreamy kind who will want to find a magic lamp on the shore of the island?

  • If you could take me out, which restaurant would you choose and which food will you recommend?

This is a cheeky and flirty question that is also very useful to find out if she is interested in you. If she flat out says she probably won’t go out with you, then you should move on. However, if she answers the question enthusiastically, this is a great way to both show that you are interested in going out with her and set the right mood for actually asking her out!

Lesson 2: Get to Know Her Past and Current Life

Now that you have asked her some fun and easy questions, it is time to get to know the real her. At this stage, you will need to be extra sensitive and try to sense how comfortable she is with your questions. Should you get the feeling that she is getting uncomfortable, then change the topic and you could even lighten up the mood with a funny question from Lesson 1. On the other hand, if she is willing to answer these questions sincerely, you will gain a deep insight into not only who she is but how she became to be who she is now.

  • Was your childhood a good one?

Make sure that you are ready to change the subject in case she did not have a good childhood and does not feel like talking about it. If you let her dwell on an unhappy memory, it could make her sad.

  • What was your ambition when you were a kid?

It will be very interesting to see what she wanted to be when she was young and what has she become now. This question could pave the way to more profound questions like what has changed if she did not fulfill her dream or what she did if she managed to become what she wanted to be.

  • Which movie do you relate to most with your own life?

Instead of asking “Which is your favorite movie?”, this question will make her put more thoughts into her answer. Not only that, but you will also find out what is her taste in movies and this could be a great indication for which movies to take her to when you want to ask her out on a date.

  • Can you tell me about your happiest memory and also the most distressing one?

This is obviously a very sensitive question, especially about the distressing memory part, so do proceed with caution.

  • What did you do on the day you turned 18?

Turning 18 is very significant for most of us and her answer to this question will shed some light on what she was like when she was young. You could follow up by asking her if she would change anything she did that day knowing what she knows now to see how she has developed since she turned 18.

  • Can you tell me about the best summer you have ever had?

This question has two purposes. First, you will bring her back to one of the best times she had in her life which will guarantee to put her in a good mood. You will also get to know more about the people who contributed to some of the best memories she has.

  • What is it like growing up at your home?

Instead of just asking the standard “Where are you from?” question which probably many other men have already asked, your question will encourage her to talk about her past and what she remembers most about growing up. She would most probably talk about her family and the people who influenced her the most and shaped her into who she is today.

  • What was your first love like?

Before you ask this question, be sure that you will not be jealous (and you really should not since it was probably a long time ago) and spoil the mood.

  • What caused the breakup in your previous relationship?

If she is willing to talk about her first love, you could prod a bit deeper with this question. You will learn about what she does not like in a relationship or if there were any mistakes made. Remember her answer and make sure that you do not make the same mistakes.

Lesson 3: Mastering the Technique of Flirting Via Text Messages

By this time, you probably already have her number so it is time to keep the flow going by texting her. Texting flirty questions is a bit different from asking her questions face to face because it could be rather cumbersome to type a very long, elaborate answer on her phone. You also could not make use of body language or tones so make sure that your wordings will not create misunderstanding.

  • When you first met me, what was your first impression of me?

This is a great question to ask her because first impressions do count a lot. If she is interested in you but had a somewhat negative first impression of you, she will naturally continue her response with a “but” followed by an explanation of how she has changed her mind. If her answer is not a positive one and she did not tell you that she feels differently about you now, it could be a hint for you to back off.

  • What was the first thing you noticed about me?

Find out what is it about you that has caught her eye – it could be a physical feature or your characteristic. Then, make use of her answer to catch her heart too!

  • So I was watching a movie yesterday and it totally made me think of you! Can you believe it?

A fantastic icebreaker question because you would have instantly piqued her curiosity and it is almost guaranteed that she would text back asking you which movie that was. This is an almost fail-proof way to get the ball rolling on a text conversation.

More: Text Messaging: How to Keep a Conversation Going

  • Did anyone ever walk in on you in a very private moment?

This question is both a little naughty and flirty. If she is interested in you, she will probably tell you what she was doing (probably something sexual) when she was interrupted in that private moment.

  • If I have only laid eyes on you but we never talked, what would be the one thing I would never have guessed about you?

There is always something that is more than meets the eye. This question will probably lead to her revealing something very profound about herself – if she wants to share it with you. It could be a habit that she thinks might be embarrassing, something she likes that nobody would have guessed, or an obsession with something weird.

  • Could you share with me an embarrassing story about yourself that you never really disclosed to anyone else before?

If the girl you like is a little on the shy side or does not tend to talk about herself, this is a fantastic question to get her to open up to you a bit. Not only will this question yield an extremely interesting answer, but it is almost a guarantee to produce some laughs. Do not forget to share your embarrassing story with her too!

  • Could you tell me the one thing that you have always wanted to do but never did?

From her answer, you will be able to find out something that she really wants to do but has not yet experienced it. Remember the answer and you can either surprise her by doing it with her on a date or offer to do it with her together.

  • Do you remember the first time you have had a steamy dream?

This is obviously a very private question but if the moment is right, you could stimulate her sexually even without being physical. You could steer the conversation this way by sharing your own experience when you first had a wet dream so she would not feel awkward answering the question.

  • Which part of your body do you like to be kissed the most?

At first, she might feel a bit nervous and awkward rather than answer your question – which is why a text message will give her ample time to compose herself and answer it the way she wants. If she is interested in you, she will tell you the answer and make sure you remember it should you ever get to the stage where you become sexually intimate.

Should she responded well to the question above, you can go a step further by asking her this question. Her answer will reveal what she likes sexually and you can then decide if both of you are sexually compatible without too high of a risk.

  • What is the one thing you find a turn off?

Knowing what she likes will certainly come in handy, but knowing what she does not like will help you avoid making mistakes and inadvertently turn a positive situation into a negative one. Take note of her answer and try your best to refrain from doing what she has told you is a turn off to her. If you have actively avoided doing it, make sure she knows it and you will score huge brownie points with her.

  • Have you ever been kissed by a woman before?

Not only is this a great question to find out her sexual orientation, but it could also lead the conversation towards a more sexy topic.

  • If you can only choose to be either attractive or intelligent, which quality will you go for?

Her answer will reveal if she thinks looks are more important than brains or vice versa. It could also shed some light on how she thinks about herself.

  • How do you usually dress when you go to bed?

A flirty and definitely naughty question that has the potential to lead the text conversation into a steamy one. However, be aware that you do not come across as a pervert when you ask this question.

  • Do you believe that a man should always make the first move?

This is a great question to find out what her values are. Not only that, her answer will tell you whether you should make the first move and ask her out now or wait for her to do it.

  • Which 3 words best define you?

It will always be helpful for you to learn how she sees herself and what are the characteristics that she values the most. Her answer could incorporate either physical looks, personality traits, or a combination of both. We suggest that you ask her to use 3 words so that you can find out whether she prefers physical over personality qualities or vice versa.

What is your opinion on friends with benefits?

From her answer, you can discover if she is all right with a relationship just based on sex and she might even hint that she is looking for something of that nature. Or perhaps she is on the look out for a more serious relationship?

  • Have you ever tried dirty talking before?

Not everyone is into dirty talking so it could be very helpful to see where she stands on this. If she mentions that it is a turn on for her, you could follow up with some dirty talking text messages. So, prepare some sexy text messages before you ask her this question.

More: Sexy Truth or Dare

  • What are the qualities you deem the most valuable in a partner?

If you believe that you have the qualities she mentioned, then make sure you tell her. If you do not, then it is high time to start developing them!

  • Do you have a soulmate?

She might have someone whom she believes is her soulmate or she could still be looking for one. She might even not believe in the existence of soulmates. Either way, her answer will probably be a profound one.

  • Have you ever had sex in a public location?

This is a bold question but a good one to find out if she prefers an exciting sex life with some risks involved or something that is more private.

  • What do you think about having cuddles in bed?

Not everyone is a cuddler so it might be important for you to know if she is one. If you do not like cuddling but she could not live without it, then you might have a problem.

  • Which do you think is sexier on a guy: briefs or boxers?

Flirty questions do not always have to be super sexual. This is a light-hearted question that could lead to laughs, discovering more about her preferences, or both. Furthermore, this could also put an image of you in your underwear in her mind which could turn her on if she is also interested in you.

  • Are we, as a human race, improving or regressing?

If she comes across as someone who is very intelligent and opinionated, this will be a great question to get her to start talking about her thoughts on life, human beings, and other interesting topics.

  • Can you name 3 values that you believe we share?

This is a great question to find out what is her opinion of you without sounding too pushy. If she thinks you have a lot in common, then it is probably safe to assume that she likes you too.

  • Have you ever had a dream where I was in it?

This is a cheeky question to find out if she thinks of you when you are not together. If she says yes, make sure to ask her to detail what the dream was about. If it was a dirty dream, then you should probably remember it and make her “dreams come true”.

  • Can you tell me 3 things that are a must-have in your idea of a perfect date?

Her answer will tell you whether she is the romantic type who prefers candlelight dinners and walking on the beach or is looking for something exciting like an adventure. Ensure that you note it down because she is practically giving you the formula of success to take her out on a perfect date.

  • Have you ever had a “love at first sight” moment?

This is a great question to find out if she is the romantic type or a more rational kind of girl. If she says yes but does not elaborate, make sure that you ask her for more details – she could be giving you a hint that it was when she first saw you!

  • What are the things you think that people should not joke about?

Learning what her boundaries are will always be handy in helping you develop a relationship with the girl you like. There is almost nothing worse than joking about something she cares deeply about and making her think you are insulting her.

  • Can you tell me which is the most attractive physical feature you find in a guy?

Every girl has a soft spot for guys with a certain physical feature. Find out what her preference is and try to develop it or accentuate it the next time you see her. If you are confident enough, you can take a picture of the feature she told you and send it to her with the question: “like this?”.

  • What do you think about girls having a sugar daddy?

Her opinion about this will tell you if she likes it when a guy spends a lot of money on her or she prefers to be independent and buy things with her own money. A girl who likes to have a sugar daddy will expect you to take her to expensive restaurants and shower her with extravagant gifts whereas a girl who does not approve of this kind of lifestyle will not feel comfortable if you spend too much money on her.

  • Have you ever reached an orgasm during sex before?

She might never have an orgasm before with someone else and if this is the case, you could take it upon yourself to help her experience it. Should she have had orgasms before, then you could ask what makes her cum.

  • What do you think about us kissing?

This is the ultimate question to find out if she is interested in you romantically or not. If she answers in a favorable way, you could immediately offer to go over to her place or meet her somewhere to kiss her. On the other hand, if she gives a negative answer, it is probably quite clear that she only thinks of you as a friend.

Now that you have gone through all three lessons, you are ready to start asking the girl you are interested in some fun and flirty questions! Remember that this is not an interrogation and you should keep the conversation flowing naturally by answering some of the questions yourself. The questions should sound spontaneous and not forced so do not try to memorize them word for word. Be confident and pay attention to her answers, body language, and facial expressions to decide on which questions to ask next. If she looks or sounds uncomfortable answering some of the more personal or sexual questions, then tone it down by asking a light-hearted question. The art of flirting is something that is not difficult to learn but it does take time and effort to master.

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