500 super interesting questions for a pen pal and more

The more attractive the girl, the more difficult it is to surprise her with anything. They didn't give her any kind of compliments. What kind of pick-up phrases did she hear? What should I tell her? How to attract her attention and stand out from the gray mass of her admirers?

You need to learn how to skillfully conduct dialogue. Give her interesting topics for conversation, ask questions that she would like to answer.

She should be interested in you. During the conversation, you should find common ground, and a note should appear in her head next to your name: “Not an idiot. We continue checking. So far the results are satisfactory.”

Start the conversation with one of the questions below. Don’t remain silent, actively participate in the dialogue, but let the girl take on the role of speaker.

Are you ready for the big game?

Then we begin!

Questions to start a conversation

  • Where did you grow up?
  • What is more important to you: appearance or intelligence?
  • What moment in your life will you never forget?

  • What is your idea of ​​a perfect weekend?
  • Are you superstitious?
  • What can lift your mood almost instantly?
  • Are you an introvert or an extrovert?
  • What's your favorite day of the year?
  • If you only had a week to live, what would you do?
  • How do you prefer to spend your weekends: at home or going somewhere?
  • Name one thing without which you cannot imagine your life.
  • What would you do if you were the last person on Earth?
  • What word do you hate?
  • Would you prefer a holiday in the mountains or at the sea?
  • What will you choose: love or money?
  • If you could invite five people to dinner, living or dead, who would you invite?
  • What was the last thing you dreamed about?
  • If you could start a music group, what kind of group would it be?
  • Imagine it's your 75th birthday. How do you imagine him?
  • What would you do if you found yourself in Russia in the 20s of the last century?

  • What situation initially seemed terrible to you, but in the end turned out to be a win for you?
  • What's your favorite word?
  • If you could choose a decade to grow up in, what would you choose?
  • What was the first concert you attended in your life?
  • If you could live in any city on Earth, what city would it be?
  • The stupidest thing you've ever spent money on.
  • Could you go a whole day without your phone?
  • If you were an alcoholic, what kind would you be?
  • What one thing would you take with you to a desert island?
  • If you didn't have to work, what would you do with your life?

Topics for conversation

There are a lot of topics, so choosing the right one for yourself will not be difficult:

  • Live nature;
  • journalism;
  • astrology;
  • fortune telling, predictions, magic;
  • hobby;
  • needlework;
  • floriculture;
  • humor;
  • story;
  • painting;
  • music;
  • movie;
  • literature;
  • photo;
  • cosmetics;
  • hair, face and body care;
  • perfumery;
  • diets;
  • accessories;
  • boutiques;
  • shoes;
  • cloth;
  • fashion events;
  • children;
  • Pets;
  • garden Garden;
  • attractions;
  • trips;
  • present;
  • rest;
  • holidays;
  • self improvement;
  • psychology of communication;
  • psychology of love;
  • psychology of relationships;
  • trainings/tests;
  • esoterics;
  • Mystic;
  • souvenirs;
  • sex (18+);
  • Sport and health;
  • weight loss and weight loss;
  • room design;
  • sewing.

Questions to make a girl smile2

  • Do you think people singing in the shower can save the world?
  • When was the last time you laughed heartily?
  • Do you know any magic tricks?
  • What's your favorite joke?

  • What funny nickname would you give to your child?
  • What's your favorite place to play hide and seek?
  • What's your favorite classic comedy?
  • Name the most embarrassing thing you've ever bought?
  • Do you remember any funny dream you had recently?
  • What's the craziest trick guys have used to get to know you?
  • What's your favorite place to travel?
  • Do you think baldness is sexy?
  • If you became a man for one day, what would you do?
  • If you were a vegetable, what kind would you be and why?
  • If your life were a movie, what genre do you think it would be?
  • What is your spirit animal?
  • Do you believe in aliens?
  • What cuisine do you prefer? European or Asian?
  • What dish would you call your favorite?
  • Name your happiest childhood memory.
  • You're a night owl or an early bird?
  • Who is your favorite musical artist?
  • Do you believe in astrology?

  • What's your superhero name?
  • What superpower would you like to have?
  • Which foreign word seems funniest to you?
  • What taste do you associate yourself with?
  • What does your nickname mean on social networks?
  • Would you like to see me again next week?
  • What fantasy world would you like to be in?

General recommendations

Very often in life the following situation occurs: a guy met a girl by correspondence, they exchanged a few phrases, and then there was an awkward pause. They have nothing to talk about. In this case, a man should have at least a small list of questions for the girl in his head. They will help to interest a girl in correspondence and start a relationship with her.

To select questions taking into account the woman’s age, her interests and your plans for the relationship, use the advice of psychologists:

  • Think in advance what questions you can ask a girl via correspondence, and which ones are best excluded from communication, or left for another time.
  • Don't be afraid to be a little vulgar and provocative. Pepper in SMS helps create excitement and intrigues lovers.
  • Read the answers carefully to avoid getting into trouble later. If a girl understands that the questions are being asked without interest, she will lie or ignore your letters.
  • Search and come up with non-standard phrases for communication. Banality is a guy’s enemy when meeting girls.
  • Communication must involve two people. If you ask questions and the lady answers them frankly, be prepared to be tested too.
  • Be sure to choose funny phrases and tasks. Humor and an ambiguous hint in a question help relieve tension and make people closer to each other.
  • Consider how busy the girl is at the time of communication and correspondence. If a question requires a deep, meaningful, detailed answer, ask it in the evening. And during the day, when you’re busy at work or school, use a list of quick phrases.

Questions to get to know her better3

  • What do you do in your free time?
  • If you could live anywhere on the planet, where would you choose?
  • What's your favorite ice cream flavor?
  • Do you prefer cats or dogs?
  • Would you like to go horseback riding if given the opportunity?
  • Do you prefer beef or chicken burgers?
  • What's your lucky number?
  • Do you have a favorite memory from school?

  • What's the first curse word that comes to your mind when someone is rude to you?
  • What is one thing you would change about yourself?
  • What is the most special gift you have ever received?
  • If you had to eat the same food for the rest of your life, what would it be?
  • Pizza or rolls? Or both?
  • What's your favorite movie?
  • If you had an endless supply of cash, what would you spend it on?
  • What quality do you value most in people?
  • Do you feel happier in a big city or in a village?
  • When you're in a bad mood, is it better to leave you alone or do you wait for someone to cheer you up?
  • If you could become the best in only one field, what would you choose?
  • If you could go back in time and give yourself advice, what would you tell yourself?

How to ask a girl in an original way “how are you”, “how are you living”?

It can be quite difficult to interest the girl you like. To do this, you should use the entire arsenal of jokes, beautiful words and compliments.

Options for unusual questions to start a conversation:

  • How is my queen doing?
  • Beauty, how are you doing sweetly?
  • Hello! What does the queen of my heart do?
  • I miss you so much, it’s important for me to know how you are doing. Tell me soon!
  • What's new in your life, baby?
  • As soon as I saw you, my head immediately began to boil with a bunch of questions: how are you? Where are you? What's new? Tell me everything!
  • How are you Tell me immediately!
  • How are you, what's new? I'm listening to you carefully!

Personal questions4

  • Name the happiest memory from your childhood.
  • Tell me about the worst date of your life.

  • What's your weirdest habit?
  • Have you ever broken someone's heart?
  • How do you behave with people who irritate you for no apparent reason?
  • Do you say “yes” or “no” more often?
  • What is the main reason that makes you get up in the morning?
  • What motivates and inspires you?
  • What things would you like to forget?
  • What do you regret most in this life?
  • Who couldn't you live without?
  • What is your main goal in life at the moment?
  • Is there anything you can say with 100% certainty that you will never do?
  • If you were a stereotype, what would it be?
  • What character trait do you consider to be your best?
  • What's the worst advice you've ever been given in your life?
  • Do you like adventure or do you prefer routine?
  • Can you tell us about the closest and most trusting relationship you have ever had?
  • What are you most afraid of?
  • What do you like to do more than anything in the world?


  1. Do you think baldness suits girls?
  2. Are there any differences between the frog princess and the toad princess?
  3. How to take revenge on your boss: put pepper in your tea or feed herring with milk?
  4. Platypus or duckbill, which is correct?
  5. If you pour water into an aquarium for a fish, will it drown?
  6. If I were an animal, what kind would I be?
  7. I don't understand what the difference is between a snowman and a snowwoman. And you?
  8. How did ancient women shave their legs?
  9. Do woodpeckers get concussions?
  10. Do bald people have dandruff?

Accompany humorous SMS with emoticons, gifs, pictures. React violently to the lady’s answer if you find it funny. Make jokes in response so that the chain of letters is not interrupted by silence.

Romantic questions5

  • Which love story that actually happened do you think is the best?
  • What do you think the best romantic trip looks like?

  • What nickname would you affectionately call me?
  • What do you think the perfect romantic gift should look like?
  • What was it about me that first attracted you?
  • What did you think of me when you saw me for the first time?
  • Do you prefer a good hug or a good kiss?
  • What does your ideal date look like?
  • What makes you happiest in a relationship?
  • Name your favorite romantic song.
  • Would you like a big, luxurious wedding or a small and modest one?
  • How did you feel when we first kissed?
  • What is your idea of ​​a perfect honeymoon?
  • Tell me what you find attractive? Just let it be something you haven’t told anyone about yet.
  • Which kisses do you like more: passionate or tender?
  • Guess what I like most about you.
  • How do you prefer a guy to show his feelings?
  • Do you like hearing how beautiful you are?
  • In a relationship, do you value conversations or sex more?
  • What was the most romantic date you were taken on?

How to ask a girl you like about her age?

The question of age for a woman can be very delicate and therefore such questions should be asked very carefully, without wanting to offend her.

Question options:

  1. Are you old enough to kiss me back?
  2. You look so confident and beautiful that it seems to me that you are older than me, isn’t that true?
  3. Will you tell me how old you are in my ear?
  4. If you were brave, would you admit how old you are?
  5. You look so good, so fresh and young, that I can’t even tell how old you are. Will you confess?
  6. I know it's tactless, but you definitely don't have to worry about it. How old are you?
  7. How old are you? Don’t be shy, I just want to know how many more years we can spend together with you.
  8. I’m embarrassed to ask how old you are, but I want to know: are you ideal for me or should I deviate from the ideal?
  9. If you don’t tell me how old you are, I’ll have to torture you with caresses for a very long time. Do you want this?
  10. How old are you? If you don't want to talk, at least give me a hint. I believe your every word.

How to communicate with a girl correctly to interest her?

Questions about what she likes7

  • What's your favorite way to spend a day off?
  • What's your favorite genre of music?
  • Tell us about the best vacation of your life?
  • What's next on your list of must-see places?
  • Tell me about your hobbies.
  • What age is your favorite?
  • What's the last thing you read?
  • Do you prefer to communicate with introverts or extroverts?
  • Name your favorite ice cream topping.
  • Which TV series have you been watching lately that has got you hooked?

  • Do you like listening to podcasts?
  • Do you have a favorite holiday? Which?
  • Do you prefer watching movies at home or going to the cinema?
  • What position do you like to sleep in?
  • How do you prefer to spend your summer?
  • What's your favorite quote from a book, movie or TV show?
  • How old were you when you first had a celebrity crush? And who was it?
  • What's guaranteed to make your day better?
  • What's your favorite day of the week?
  • Do you prefer reading books or watching movies?
  • Do you prefer breakfast, lunch or dinner?
  • As a child, did you eat bread crusts on sandwiches or ask them to be cut off?
  • What calms you down?
  • What is your favorite time of year and why?
  • What app do you use most often?
  • Would you rather cook the food yourself or order delivery?
  • Do you like board games?
  • What kind of coffee do you prefer?

  • If you could have any exotic animal, which one would you choose?
  • Your perfect way to spend your birthday.


Use intimate questions when communicating with a girl you don’t know well, if you feel that she doesn’t mind, they won’t confuse her. In other cases, leave them for later, when the relationship is a little stronger.

Vulgar phrases in correspondence take communication to another level, help create an intimate atmosphere and give a reason for a date. But they must be correct, careful, so that the guy does not look like a sexual maniac.

  1. What was your first sex like?
  2. Have you experienced a real orgasm?
  3. Do you have unfulfilled sexual fantasies?
  4. Do you like making love in unusual places?
  5. Do you approve of unconventional sex?
  6. What part of a man's body seems most attractive in bed?
  7. Does the size of your manhood matter to you?
  8. How do you feel about hard sex?
  9. Do you go to adult stores?
  10. Favorite position for making love?

On a note! Girls themselves can hint at a meeting with the help of provocative questions, hints at a love meeting. The main thing is to notice the ambiguity of the correspondence and get your bearings in time and take a decisive step.

Career questions8

  • What do you enjoy most about your current job?
  • What irritates you about her?
  • What achievements in your career are you most proud of?
  • Do you think you will stay at your job for a long time or not? And why?
  • Are you one of those who “work to live” or “live to work”?
  • Does your job make you feel happy?
  • How would your ten-year-old self react to what you're doing now?
  • What do you remember most about your first job?
  • How old were you when you first went to work?
  • Name the worst job you've ever had.
  • What initially interested you in your current profession?

  • Have you ever had a part-time job?
  • What's your favorite part of the workday?
  • What's the best decision you've ever made in your career?
  • What job advice would you give to a younger version of yourself?
  • How do you differentiate between your work and home life?
  • Are you waiting for retirement or are you going to work as long as possible?
  • What do you think about workaholics?
  • Do you have a best friend at work?
  • How do you motivate yourself at work?
  • What surprised you most when you first started your career path?
  • How do you collect your thoughts again after making a mistake?
  • What does your family think of your work?
  • Who influenced your career choice the most?
  • If you could change everything, would you choose your current job again?

How to ask a girl you like her phone number?

Some guys are embarrassed to ask for a girl's phone number, and thereby miss the opportunity to make a romantic acquaintance. Unobtrusive and positive questions, based on all the rules of “successful flirting,” can help with this.

Question options:

  1. Girl, I lost your phone number and it's the worst thing that ever happened to me. Can you help me remember it?
  2. Girl, if I had your phone number, I would probably be the happiest! Won't you make me happy?
  3. You know, today is my birthday and you can give me the best gift in life - your phone number.
  4. I know it's not original, but I'm so impressed by you that I don't want to miss the opportunity to meet you. Would you mind leaving me your phone number?
  5. Girl, I’m ready to agree that you give me the full phone number, forgetting to give one number. And then I will prove that I can reach you on the phone. Will you make me happy?
  6. To be happy, I only need two things: your name and phone number. Will you help me become happy?
  7. What a pity that we don’t have mutual friends. I would definitely get your phone number, but now I just have to beg you to give it to me.
  8. If I had one wish that could come true, it would be your phone number. Don't know where to find the nearest magic genie?

How to ask a girl for a phone number beautifully?

Questions about family9

  • How much time do you spend with your family?
  • Who in your family do you most enjoy spending time with?

  • Are you close to your family?
  • Who in your family are you closest to?
  • How would you describe your family now?
  • What's your favorite family tradition?
  • Have you ever wished you were raised differently?
  • Have you ever hidden anything from your parents or lied to them?
  • Would you like to have more brothers/sisters?
  • If you started a family business, what would it be?
  • Does your family have affectionate nicknames for each other?
  • What is the most important holiday in your family?
  • What would surprise your family the most if they found out about you?
  • How do you deal with family disputes?
  • What is more important to you: family or friends?

About relationships and love

If you don’t know what to ask a girl about in correspondence, move on to the topic of love and relationships. Ladies love to carry on conversations on personal topics. A conversation about relationships helps to get to know your interlocutor and establish close contact.

  1. Do you often fall in love?
  2. Did you confess your love first?
  3. Do you know what unrequited love is?
  4. Is romance a necessary part of a relationship or can you do without it?
  5. Can you call first after a fight with a guy?
  6. If a man cheats, will you forgive him?
  7. Do you believe in horoscopes?
  8. Does friendship between a man and a girl exist?
  9. The ideal guy, what is he like?
  10. Do you believe in love at first sight?

Questions about values10

  • If you only had one sense left (smell, touch, etc.), what would it be?
  • Tell us about your definition of success.

  • What makes you feel safe?
  • What are you most proud of in your life in recent years?
  • What do you admire most in the world?
  • Would you rather earn more money doing a job you hate, or earn less but do what you love?
  • What's the first thing you notice when you make new friends?
  • How has your perception of the world changed over time?
  • How can I earn your trust?
  • Do you have a motto that you use in life?
  • Do you like what you see in the mirror?
  • Do you believe in life after death?
  • Do you trust your intuition or logic more?
  • Is there someone you truly hate?
  • What mark do you want to leave behind in this world?
  • Would you lie to keep your best friend out of jail?
  • Do you consider yourself a good person?
  • Do you think a man and a woman can be just friends?
  • If you could erase unpleasant memories from your memory, would you do it?
  • Would you like to live forever if you could?

How to ask a girl you like how many boyfriends she's had?

Such questions are very intimate and not every girl will want to talk about this with a man, and if you have the opportunity not to ask about the number of guys, it’s better not to do it. However, if you want to test the sincerity of feelings or learn more about the person you are in a relationship with, ask the question in a humorous or sensitive manner.

Question options:

  • I understand that I’m not your first man, but, to be honest, I would like to know how many guys you had before me. Won't you share with me?
  • Let's talk to you about intimate topics? I’ll confess to you how many girls I’ve had, and you’ll tell me how many guys you’ve had.
  • I love you very much, but one obsessive question does not leave my head: how many boyfriends did you have before me? Believe me, I won't be angry or jealous. I just want to know more about you.
  • It seems to me that you are still such a heartbreaker! Admit it, how many men’s hearts have you already broken before me?
  • You are so charming that I have no doubt that men adore you. This is true? Have you enjoyed popularity and male attention? Have something to brag about?

How to ask a girl a question on an intimate topic?

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