Questions to Ask a Guy Over Text

Questions to Ask a Guy Over Text
By Subhash Das Updated

This generation is bold enough to know interesting questions to ask a guy over text. Not only girls, guys love it too when they are asked interesting and fun questions. Text messages are a great medium to connect with a number of people. But, the real game is set only when you know which type of questions can stimulate the attention.

100 Questions to Ask a Guy Over Text

It is quite important to know the pattern of questions to ask him. Not every question is suitable for every mood and occasion. To make things more interesting, a stunning list of questions to ask a guy over text has been compiled. Enjoy and savor everything presented here. So, without further ado, let’s start the interesting chat.


You have got such an awesome physique, what’s the secret?

Flirty question! Of course, it is honey. If text messages look dull, life will be monotonous. So, why not to send him something cool?


Which girly move you find absolutely stunning?

This question is a direct cue that you like him. Well! Play it fairly. Let him share his point. These type of questions to ask a guy over text are brilliant and quite safe as well.


What makes you unique in your office?

This is a beautiful question to ask any guy. It has the brilliant punch of philosophy and wisdom. Awesome, right?


Last time, when did you go to a bachelor’s party?

Bachelor’s party is the heaven for all the unmarried guys. And generally, guys remain pretty excited about it. Surely, he is going to be surprised by this question because girls rarely show any interest to this informal carnival of guys.


Which is your favorite party wear?

Why should girls have all the fashion? Guys are fashionable too. Ask this to your guy. And, next time you can gift him something of his choice.


Do you believe in supernatural things?

Supernatural thing is quite a debatable topic. But, you don’t need to indulge in something like that. Just flow with the question and let him answer it.


How do you judge a stranger?

Some questions draw a deep line in our hearts forever and this is one such. This question is the perfect blend of wisdom and presence of mind.


What is your favorite game of all time?

Whether your guy is a gamer or not, this is something that every guy loves to talk about. Surely, these are one of the coolest questions to ask a guy over text.


Which dish none can cook like you?

Interesting Questions to Ask a Guy Over Text

We all know that all the brilliant chefs all over the world are guys. They do it the best. Know what your guy cooks the best.


Romantic genre or thriller genre – what is your favorite one?

Some believe that romantic genre is totally for girls, but that is not true always. What’s your guy loves to watch? You need to ask this question to know more about him.


Have you ever cried while watching a movie?

Who says that masculinity doesn’t portray emotions? They do because emotion is a humanly feeling. Ask this question to reveal a different side of his character.


What do you usually take on dinner?

A very basic question to ask him for sure. This lifestyle related question reveal a lot about the person, so try to know him more.


Which pickup line is your favorite?

Pickup lines are catchy and sassy, but sometimes few lines sound casual but say a lot of things. Who knows, maybe you will find your favorite pick up line after asking this question.


What is the craziest thing to do on the first date?

Of course! You are actually asking to hear his first dating experience. And, what can be better for that than these type of questions to ask a guy over text.


Can you describe your mood in two words?

It is a difficult one for sure. But, why should the question be easy all the time? Make it twisted and tweaked.


Which dance move you practice often?

He might be or might not be a great dancer, but he might be quite interested in dancing. Ask this light-hearted question to scoop out a secret part of him.


Would you ever donate all your money to a charity?

A noble question for sure, but don’t need to judge him on the basis of this. It depends on the perception of individuals. Whatever his answer is, accept that.


Which childhood memory inspires you the most?

Our present is somehow latched with our past. Childhood is the most precious time for anyone. Ask your guy to hear something motivational. Amazing, isn’t it?


If you want to date someone this weekend, who would that be?

Wow! Sounds interesting. This question is quite a direct approach for any guy that would take you straight to his heart. Well! Surely he is going to love your boldness.


What is your favorite attire in your wardrobe?

We all have a single piece of attire that we love to wear on almost every occasion. What’s his? Only this question can lead you to the answer.


What do you do when you feel sad?

This is one of the many important questions to ask a guy over text in order to know him more. So that, next time you can help him to eliminate the root cause of his sadness.


What is the most beautiful part of a relationship?

Romantic Questions to Ask a Guy Over Text

When a guy finds the term ‘relationship’ on his mobile, he starts feeling excited. Well! Not us, this is something experts have shared. And, there is no harm in giving him a subtle hint, so are you ready for that?


Which is your favorite food of all time?

Whether your guy loves food or not, he definitely has a cuisine in his list that he loves to eat.


So, what’s your weekend plan?

This is one of our favorite questions. You are not asking a question only, but actually giving him a subtle hint to go out with you this weekend.


What is the most awesome compliment you have received till date?

Some compliments remain in our memory forever. Try to know his share of beautiful compliment, so that next time you can impress him secretly.


Which sports are your absolute favorite?

For any guy, answering sports-related questions is like hitting the jackpot. And, we love it too. Undoubtedly, this is one of our favorite questions to ask a guy over text.


What would you do if you suddenly wake up at 2 am in the morning after having a nightmare?

This question is really spooky. So, get ready to hear something supernatural and ghostly story.


What is the most memorable memory with your parents?

Parents are such a beautiful part of our life. We create life-long memories for them. What’s his best moment with them? Ask this interesting question to know the answer.


Have you ever played a prank on anyone?

If the guy is naughty, then this is the best chance to ask him such fun question.


What will you do if you fail to achieve something again and again?

Failure is a part of life, but what to do when it strikes again and again. Ask to know his point of view.


What is the most exciting thing in your life?

If your guy is fun loving, then he would love to answer it. So, are you excited enough to know his thoughts?


What do you do at late night?

Late night plans are usually secret, but if he wants to share, you should take the opportunity. So that next time, you can accompany him.


Why are you still single?

Ahem! Quite a flirtatious and cute question. This is undoubtedly one of the best questions to ask a guy over text.


What’s the best thing to do on birthday?

You have just asked him about his actual birthday planning. Brilliant question for sure, isn’t it?


How do you want people to remember you?

Quite a different question to ask a guy. But, he would be happy for sure to answer it properly.


Do you love cartoons or cartoon movies?

Who says that this genre is only for kids? Anyone can love it. What does he say?


Which country do you want to visit within this year?

Everyone has a dream. Try to know his upcoming plans on vacation trips so that you can happily join him.


What do you want to do within the next 5 years?

Don’t just consider it as a typical interview question. We find it quite a hilarious question to ask over text.


What do you find attractive in women?

Quite a progressive question to ask. Well! This is the spirit that every guy loves. We are absolutely in love with these type of questions to ask a guy over text.


How many scores would you give your intelligence?

Quite a brilliant question which is tough to answer for any guy. But, your guy would happily answer you.


How do you boost your confidence?

Have you just asked him to share one of his secrets? Well! Get ready to borrow some confidence from him. What do you say?


What’s your favorite car?

Cars can be called the second love of any guy. Won’t you love to know about your rival?


What is the most beautiful thing to ask on the first date?

The first date would surely give him some goosebumps. Try to save the answer somewhere for future reference.


What is your favorite topping on an ice cream?

Ice cream is something that can melt anyone’s heart. If you are a hardcore ice cream lover, then you need to know about it.


What is the best surprise you have got till date?

Who doesn’t love surprises? You truly need to know this answer so that next time, you can surprise him too with something like that.


Which junk food chain is your favorite?

He might be calorie conscious but there has to be one junk food chain that he loves. Next time, you can join him too there. This is one of the yummy questions to ask a guy over text.


Do you love to do charity works?

You shouldn’t judge him by asking this question because it is all about perception. But definitely, it is a nice addition to this list.


Have you ever performed on stage?

Cute Questions to Ask a Guy Over Text

One such question where you are trying to peek through his life. Lovely question, isn’t it?


What was your favorite subject in school?

A conversation is incomplete without a casual and fun question, and this is one such question. It is definitely a cute question to know about his school days.


What do you do when you are home alone?

We all do craziest things only when we are home alone. Such opportunities rarely come into our lives. Thus, this question is very bold in nature.


How would you describe yourself in one phrase?

It is indeed a difficult question to answer. But, why should leave such a golden opportunity to test his wisdom?


When did you feel that you have achieved success in life?

Success has no perimeter or definition. It varies with every aspect. Sail yourself on his beautiful journey.


How did you take criticism?

Not everyone has the capacity to take criticism positively. Are you excited to know his perception?


Has anyone ever compared you with any movie actor?

We find these questions to ask a guy over text very cute and upfront. Surely, you are giving him some hints.


What is your favorite party track?

If a party is all in his mind, then this question would blow his mind. Be ready to make some noise with your party guy.


What is the most daring thing you have ever tried?

The list might be pretty long in his case; let him share one such thing that is unforgettable. Don’t you find this question to be pretty interesting?


Which type of burger is your favorite?

There are some unique types of burger all over the world. Make sure to take him with you someplace like that.


What was your expression when you tried egg for the first time?

Don’t be surprised to find back to back food related questions. This is going to work awesome if your guy is foodies too. Asking back to back, such questions would tempt him to plan a surprise date night. Aren’t you excited?


Do you have any strange habit?

Human beings behave strangely sometimes, so don’t be surprised to hear something creepy.


What are the qualities you want in your partner?

Quite a vital question at the point when you have a lot of interest in him. Obviously, his answer would help you to shape your equation with him.


Which movie have you watched recently with your family?

If your guy lives with his parents, then this is a beautiful question to ask him. In this way, you would come to know about his family and the special bonding they share with one another as well.


What do you find very strange among your friends?

Friends or buddies are someone, with whom we share a very special bonding. These type of impressive questions to ask a guy over text sound extraordinary always.


What is the best thing about your hometown?

We all find our hometowns very special, and he would be no different too.


If a hot girl proposes to you, what would be your reaction?

Lovely Questions to Ask a Guy Over Text

Wow! That’s what we call a super sensual question. So, don’t blame him if his answer goes to some other path.


Have you ever met your doppelganger?

A fun question for sure. If he has met, then you can definitely expect some interesting storyline from him.


If you were the president of your country, what else could you have done for your countrymen?

Well! Don’t awake the statesman inside him. This is a question which would test his presence of mind for sure. So, take it easy.


Which historical people never gained the popularity that they were supposed to?

If reading various types of historical books is his hobby, then he would love to answer it. And of course! These type of questions often become an elongated chat. So, be prepared for that.


What is the highest number of messages you have ever sent to anyone in a day?

We consider it to be a very cute question to ask a guy over text. Sometimes, this sort of question helps a lot in bringing two people closer.


Which activity never makes you feel bored or tired?

Sometimes, a tweaked question can bring a lot of life to an odd topic. Ask him about his hobby in a different way. Crazy, right?


Which mobile app is your current favorite?

With the advent of new technologies, the app market is flooded with apps. So, who knows that with this answer, you might end up finding your fav app.


What’s your favorite food in depression?

This generation loves to explore a variety of foods and tags. Surely, he would love to tell you his food that he eats in depression. Well! Food energizes the mind, and this type of question proves that.


What’s your hidden talent?

Hidden talents make us special and most importantly, everyone has at least one. Aren’t you excited to know his hidden talent? These type of questions to ask a guy over text are enough to glue his eyes to the screen.


Do you love to help strangers?

Good Samaritans are rare nowadays, so don’t get upset if an unusual answer comes from him.


What do you do to keep yourself happy always?

Happiness is a rare virtue. So, if your guy remains happy most of the time, won’t you want to know the secrets?


Are you passionate about anything weird?

Passion follows a dream, and eventually together they create a story. Is there anything bizarre he is passionate about? Well! Only his answer will lead you to the cue.


What’s the cutest question anyone has ever asked you?

Beautiful Questions to Ask a Guy Over Text

Cuteness is not limited to any gender or to any age group. We believe that this is itself a very cute question to ask a guy.


How would you protest if you find anything anti-social activities?

It is necessary to express vehement, but not everyone loves to do so. Is your guy a peace lover? Find out with this question.


What’s the best selfie you have ever taken? Can you send me the pic?

Of course! You have to ask for it, he is definitely not going to you the pic just like that.


What is the first thing you do when you get up in the morning?

Morning chores are different for different people. Let him disclose everything about him.


Have you ever fallen in love with someone by only hearing her voice?

It is going to be a blend of a beautiful and an incredible question at the same time. Well! Let him tell you the story then.


Which show on tv do you find very strange?

We might love Tv shows but there would always be one show that we just hate. This is definitely one of the different and off-beat questions to ask a guy over text.


Will you ever disclose your computer password to anyone?

Interesting question, isn’t it? We disclose everything to those people whom we trust. The answer would definitely lead you close to his heart.


Which art form you find very intriguing?

Every art form is beautiful and different. Often, we love to talk about everything aesthetic in life. So, you should definitely ask these type of questions.


What keeps you energetic?

Don’t you love it when someone praises you? Well! He is no different too. This question is actually applauding loudly how energetic he is.


How do you manage your time?

Time management is an art, and not everyone can do it efficiently. But, if he can, that is no less than a blessing.


Your skin looks amazing, what’s the secret?

Guys are mostly very casual about skincare, but not everyone. Some guys are way more particular about the regime than girls. So, if he is like that, you can definitely take some inspiration from him.


Are you obsessed with anything?

Obsession has no age limit. Anyone can be like it. Try to know his obsession if he has any. It would help you to unfold a lot of mystery.


Which gadget is your favorite?

Awesome Questions to Ask a Guy Over Text

Admit it or not, we all love gadgets. This text message would create a lot of scope for an elongated conversation between you two.


What is your favorite season?

This might seem like a basic question, but quite a beautiful question that can be asked to anyone.


What do you find very funny in your character?

Well! Not everyone likes to admit it. Though we find this question very amusing. This is one of the funniest questions to ask a guy over text.


What makes you very special?

There might be very few people who can answer this question. But, that must not prevent you from asking this question. This is a very special question indeed.


What do you do in your spare time?

Spare time is the best entertainment time for many of us. We absolutely adore this. This is one such question which always creates a long discussion.


Does dream come true?

This is quite a debatable issue and people differ in opinion. For some, their dream has indeed come true, while some would go totally against it. Whatever the debate is, this question is on the wiser side.


Do you believe in fortune?

Men build their own fortune, this is what few people believe. While some have totally sacrificed themselves before fortune. Aren’t you curious to know to which category he belongs?


What do you hate the most?

This is one of the off-beat questions to ask any guy. But, sometimes few things become necessary to know and this is one such question.


What is the tagline of your life?

We all love to describe our life in one sentence. It sounds chic and cool. What’s his?


If a movie is ever made on your life, what would be its name?

We just love it and that’s why this of our favorite questions to ask a guy over text. Well! Don’t expect any polished answer from him. Because it has no prototype at all. Just let him flow in the imagination.


Have you ever sent an embarrassing text message to your class teacher?

Probably, we enjoyed the most during our school or college days. That was the best period of our life. But, admit it or not we have a bunch of embarrassing stories too. What is his story? Only he knows the best.


If an average looking girl proposes to you, what would be your line of action?

Interesting question, isn’t it? Every guy wants a beautiful girl in his life. But, are all the same? What’s his take on it?


If your best buddy cheats on you, how would you take that?

It is not an easy thing to digest backstabbing. How your guy handles it, it is definitely something to think of seriously.

These are the top 100 questions to ask a guy over text. The list contains a variety of interesting and fun questions to ask your guy. The list is actually ever expanding. But, all these information are absolutely stunning and abreast. So, which one is your favorite?

List of Questions to Ask a Guy Over Text


  • Always make sure to pretend his mood.
  • Do not spoil anything by asking unnecessary irrelevant questions.
  • Spare him if he doesn’t want to answer a certain question.