201 Questions To Ask a Guy in person, or through text - never seen before

Most conversations are made out of questions and answers which then lead to replies to replies. Hence, a good question leads to a good conversation; an interesting question leads to an interesting conversation.

Whether you’re looking for things to ask a guy to keep the conversation going, or questions to ask to know him better, or questions to make a conversation fun and memorable; I’ve got you.

I’ve got a full list of 201 questions to ask a guy: questions to ask in person, and questions to ask through text. Choose carefully, write them down, or print them, because these are, indeed, remarkable.

Let’s get this started!

Funny & weird questions to ask a guy – Laugh it off together

We’ll start off with something to bring laughter to the conversation: funny or even weird questions to ask a guy. It doesn’t matter whether this guy is someone you want to impress or someone you know for a long time, or if he’s your boyfriend; Hell, you can even ask these questions to your guy friend!

Here’s the list, madam:

If everyone was obligated to participate in a talent show, what would your performance look like?
Will you tell me the lamest joke you know?
What’s something stupid you believed in as a child?
Do you have messy visitors, or are you a messy one?
Is there something you thought was amazing until you tried it?
What’s something that’d ruin your career if your boss would find out?
Would you date the female version of yourself?
How would you describe the worst first date there could be?
How would you describe the last ‘ick’ you’ve got from someone?
What’s the weirdest phase you’ve gone through?
What would you do if you were a woman for a day?
What’s the most embarrassing thing you’ve done in public?
What do you think is the weirdest way to meet someone?
Is there something you exaggerated and had a funny outcome?
How was your first kiss?
What’s the most embarrassing thing you did as a child?
Were you ever curious to wear girls’ clothes?
What’s something you just can’t seem to figure out about women?
How do you think your ex would describe you?
Do you watch a movie you don’t like until it ends or leave it there?
What’s the worst pick-up line you’ve ever used?
Is there a movie that everyone saw but you? (follow-up with why)
Is there something you hide from your friends because it’s a guilty pleasure?
What’s your recipe for a happy day?
Is there something you hate doing, but you have to do it every time?

Interesting & intriguing questions to ask a guy – Wow along in the conversation

There are good questions to ask a guy. A good question is an interesting, intriguing question; one that needs a while to answer. So, what are some really interesting questions to ask a guy?

I carefully crafted 25 interesting and intriguing questions for you to ask a guy. Here:

What type of an old man do you think you’ll become when you grow old?
If your childhood dreams would come true, what would you be doing right now?
What do you think is the rarest quality a person can have?
If you would be able to record 2 memories and keep them forever, which ones would you choose?
How would your friends describe you?
If people wouldn’t be able to see you, what’d you think would attract the most to you?
You’re only allowed to get 5 things from your house to go to an unknown place, what would you get?
What’s something you wish everyone knew/heard/saw?
If you had the chance to relive your life, would you do it?
Let’s say an alien decides to visit you and wants to know the most beautiful thing on Earth; What would you show the alien?
If you could choose to experience a day in the life of any animal, which one would you choose?
If an alien visited you and had no idea what music is, what piece would you show it/him/her?
If you could live in any movie, which one would you choose?
What impresses you the most about humans?
If you could spend an entire day on an island with anyone dead or alive, who would it be?
What would be your superpower in a sci-fi movie?
Do you love yourself? If so, how?
When was the last time you lied when someone asked you how you are?
What would your advice be to someone having a bad day?
If the entire world followed your advice, what would your advice be?
What do you think the world will be like 50 years from now?
What do you think the world would look like if all people were like you?
What would you do if right now you’d be the only human on the entire planet?
What’s the best compliment you’ve ever gotten, and why do you think it’s the best?
What do you enjoy most about your days?

16 ways to win a guy’s heart on the first date

Questions to ask a guy to get to know him deeper

There are certain questions to ask if you want to get to know a guy. Those are questions to ask him to know his intentions, and to get to know him better.

The good questions to ask a guy you like are also the ones that lead to deeper conversations. So, what to ask a guy to get to know him better; to get to know him on a deeper level? Here they are:

How are you doing, honestly?
What’s something very interesting about you that I don’t know of?
When was the last time your eyes shone out of joy?
Who’s a person that had a huge impact on who you are today?
What’s something small that you get overly happy about?
What do you value the most in a person?
What calms you down after a long tiring day?
What’s your opinion on social media?
What’s your saddest memory? Why is it the saddest?
Whose sadness has the power to make you sad too?
How would you describe your connection with your family?
When was the last time you cried?
Is there something/someone you wish you had more time for? (If yes, what is it?)
Is there a common reason your relationships ended?
Would you say you’ve had your heart get broken by someone?
What is something that could easily ruin your day?
How would you describe a person you can’t stand? What would their personality traits be?
What’s your most precious memory?
What do you spend most of your money on?
What do you look for in a relationship?
How do you practice self-care?
What motivates you to live?
What are you most grateful for?
How many people do you fully trust?
What do you think about the idea of fate and destiny?

Random & simple questions to ask a guy

These are simple questions you can randomly throw in a conversation if you want to keep it going with a guy. If a topic leads to one of those, or if the silence kicks in and you want to break it, these will just do the work. Random and simple, here we go:

What’s the perfect weekend for you?
Tell me something I don’t know about you
How would you describe yourself in three short words?
Tell me about a talent of yours… your favorite one!
What’s a question you’d like to be asked?
Is there something you need to talk about, but couldn’t do so?
What’s a trend you can’t stand these days?
What’s something you cook amazingly?
What’s your favorite thing about being in a relationship?
What’s something about you that you wish people around you would notice more?
Do you consider yourself to be an expressive person?
What’s the most interesting thing you’ve heard today?
What’s your idea of romance?
Do you believe in religion?
Do you have a lot of close friends?
What places did you visit?
Do you enjoy traveling?
Describe to me what your perfect, ideal day would look like?
What’s your idea of relaxing?
Do you have a secret place in which you find aloneness when you need it?
If money wasn’t a thing, how would you spend your days?
Do you have a comfort food? (If yes, what is it?)
What’s something you’d never tolerate?
Do you have any fears? (Follow-up question: what are those fears?)
What do you think of astrology?

Flirty questions to ask a guy

Flirting with a guy is a way to spice up the connection. It gets even more interesting with the questions added to the flirting. If delivered the right way these will take your flirting to a whole nother level:

How do you think it’d be my reaction if I could read your mind?
If you could hypnotize me and make me do anything for you, what would you make me do? How?
How dare you be this good-looking?
Would you say you’re much of a heartbreaker?
What do you think you’d find out if you’d be able to read my mind right now?
How did you end up so handsome? Any secrets you’d like to share?
Do you consider yourself a flirty person? (If the answer is yes, follow up with “Would you mind showing me?”)
What do you think about me when you’re all alone?
What got you drawn to me?
What do you think is the most attractive thing about me?
Do you notice yourself shining when you smile?
You have this type of glow, are you aware of it?
To be honest, were you that one guy at school that got girls running after you?
What do you like most about the time you spend with me?
You seem to be an interesting guy, tell me the most interesting thing about yourself.
Do you know that I like you?

Dirty questions to ask a guy

These dirty questions won’t spice up the conversation… no, they’ll set it on fire!

What do you think about the idea of sleeping naked?
What’s your idea of sexy?
Do you consider yourself to be kinky?
What turns you on the most?
What gets you easily weak (sexually speaking)?
What’s your favorite erotic movie?
If you could live in an erotic movie, which one would you choose?
What would your porn nickname be?
What’s the dirtiest thing you’ve said to a woman?
How would you describe the hottest fantasy?
Clothes on, or off?
What do you think is the most inappropriate place to have sex?

“This or that” questions to ask a guy

Short and simple, these “this or that” questions will make the conversation more fun. You can make it a bit of a game and ask them one after the other, or just ask them randomly every now and then to get to know more about the guy; your choice.

A trip around Europe or a new fast car?
Beach or mountain?
Sugar or no sugar in your coffee?
A place of calm or a place of noise?
Sci-fi or horror movies?
Online or in-person?
Hot weather or cold weather?
A walk in the city or a hike in a mountain?
Rich or happy?
Grateful or bored?
Attention or love?
Ice cream or frozen yogurt?

Questions to ask a guy through text

Questions are one of the ways to keep a conversation going with a guy over text. I’ve crafted a pretty big list of questions that you can ask a guy over text. There are a few categories:

Questions to ask over text to keep a conversation going with a guy
Deep questions to ask a guy over text
Flirty questions to ask a guy over text
Questions to ask a guy over text to see if he likes you

Knock yourself out!

Questions to ask over text to keep a conversation going with a guy

A fun and hilarious text conversation will require fun and hilarious texts and questions. An interesting and deep text conversation will require interesting and deep questions.

These are your fun and interesting questions when in need of continuing the conversation with your guy. Keep it going fun, deep, and interesting:

Will you send me a picture of the most beautiful thing you have around right now?
What concert do you wish you went to but missed for some reason?
What do you get easily mad at?
Would you say you’re a talkative person?
How would you describe your relation to your phone?
Did you ever accomplish a new year’s resolution? How did you do it?
What’s something mind-blowing you recently found out?
Do you have any embarrassing stories you’d like to share with me?
What music have you been listening to recently?
What was your favorite movie when you were a child?
What memory would you relive?
What’s the last positive text you sent today?
What’s the last thing you googled?
What’s the weirdest text you’ve sent by accident?
Will you send me a meme, and bet on whether it’s gonna make me laugh or not?
Have you ever ghosted someone? (If yes, why?)
What do you consider to be selfish?
How would you like to spend the holidays (ideally speaking)?
What was the best thing about your day today?
How would you describe your best personality trait?

*Feel free to add emojis, gifs, or memes to make your questions more fun!

Deep questions to ask a guy over text

Whether you’re texting in the initial stages of dating, or you already know one another a bit, or you’re in the texting phase with a guy; these deep questions will get you to know him better through text:

What do you think makes a relationship work?
If you had the chance to live your life differently, how would you do it?
Do you express yourself emotionally a lot?
What do you think makes a person a decent one?
Imagine your worst day, what would make it better?
What do you think of horror movies in general?
What behavior annoys you the most?
Would you say you’re more of a giver or a taker?
What’s something you think would improve people’s life 100%?
Where do you think is the ideal place to meet a potential partner?
Is there a person that always cheers you up when you’re in a bad mood?
What childhood memory would you replay?
What’s your favorite childhood memory?
What do you wish you didn’t judge, but can’t help but do it?
Beach, mountains, or city?
Do you have any stories that your friends consider unbelievable?
How do you like to travel?
What do you think makes you a good friend?
How would you describe your connection to the world in general?
Do you have any regrets?

Flirty questions to ask a guy over text

There are fun flirty texts you can send a guy to make your texting conversation more interesting; however, these flirty questions will spice it up even more:

I’m curious to know, why do you text me?
Do you know your love language? Which one is yours?
Is there something you’re hesitating to text me?
What would you think a date with me would be like?
What do you like most about texting with me?
How would you describe a perfect date with me?
Are you trying to flirt with me?
Do you think I’d make a good flirt?
What would you like to do together if/when we’d meet in person?
Is there any topic you’re dying to discuss?
What do you think when you think of me?
Would you like to know what I think of you when I think of you?
I thought of you today, want to know what?
How about we drop the bs, and start flirting?
How do you manage to be such a good flirt?

How to flirt with a guy over text?

Questions to ask a guy over text to see if he likes you

That’s a sweet phase to be in (not knowing if a guy likes you or not through text). I’ve got you covered with these 6 fun and easygoing questions:

Will you send me the coolest picture you’ve seen today?
Did you tell your friends how awesome I am?
How would you describe the ideal girl’s personality?
What do you think of our text conversation so far?
How would you react if you’d see me today?
From 1 to 10 (10 being the highest), How would you rate this text conversation?

What to talk about with a guy on the phone? – What are the good things to talk about with a boy over text?

When it comes to things to text about with a guy, you want to find good conversation topics, something worthy of your time while texting; Something to impress one another with.

I’ve picked some good conversation topics for texting for you for when you find yourself stuck and not knowing what to talk about with a guy over text; These will do wonders:

Free time – What you do in your free time, your hobbies, etc.
The world – Your visions and thoughts on the time and world we’re living in.
Jobs – Your past, and current jobs, if you’re happy or not with them.
Common interests – Something you both enjoy is always a good topic.
Foreign languages – Talk about whether you know a foreign language, or if you’d like to learn a new one.
Music – Favorite, least favorite music to listen to. Talking about music, even sharing it, never lets you down.
Movies/movie series – Just like the music, the topic of movies/movie series is a worthy topic to discuss. Your likes and dislikes on it; it will get you both to know more about each other.
Cities – What cities you’d like to visit, what cities you like, what cities you dislike, it’s just so much to talk about.
Science – If you’re into science, and know or like to know more about it, then texting about it is a pretty good idea; you won’t sense time passing.
Books – What books do you like, what books changed your life, etc. Just like movies and music, the taste and preferences in books tell a lot about you.
Personality types – This is a good topic to talk about when texting a guy when you want to know him better. Discuss your personality types, explain and discover more about one another.
Ask “this or that” questions – This or that questions are easier to answer, and you get to know more about one another. It’s fun and engaging, it’s one of my favorite things to talk about with a guy over a text message.

Those were all 201 questions to ask a guy in person or through text, and 12 topics to talk about with a guy through text. Choose what makes you comfortable talking about, and something that shows more of your personality.

Good luck,

Callisto