Last updated on January 2nd, 2023 at 02:04 pm
No good conversation started with a boring question. The same goes for dating. If you think you can hit on that one girl/boy you’ve been meaning to talk with a good old “How’s it going?”, you won’t get very far. Sometimes, to strike a good conversation, you have to approach things with more creativity, which is why we decided to outline some of the best conversational questions to ask on all sorts of occasions.
Before we jump into the questions themselves, we’d like to set some ground rules and clarify a few things in advance as it will make things easier for both you and us. First of all, there’s no guarantee that these questions will hit home as it depends on the person. And secondly, no, you are a skilled talker, you just don’t realize that yet. Alright, now that we got this out of the way, on to the questions themselves.
The first point on our list features the main questions. Some of you might be wondering, what are these main questions? Aren’t all of them are main? And the answer is no, not all. The main questions are the ones you ask when you just met. You ask the main questions when you want to learn the basics about the person. Some of the most crucial Qs to ask are the following.
- What do you do for a living? Do you like it?
- What is your favorite thing to do in free time, or in general?
- Do you have a hobby or something?
- Where were you born? Was it a village or a big city?
- What are your lifetime goals? Are you working on them?
- What drives your decisions?
- Are you a calm type of person? Or do you like to party all night long?
- What kind of music do you like?
- What is your dream destination? What country would you like to visit the most?
- What do you like better? Coffee or tea?
Good questions to ask a guy you just met
These questions are very safe. They won’t touch upon hot topics such as religion or politics, which makes them perfect to ask a guy you like without looking overly invested. Think of them as great conversation starters and not relationship questions. After all, it’s best to not go over the top before dating him. We’ll also throw some yes or no questions into the mix for you to not sound obvious. In any case, take a look at some ideas.
- Do you like your job? Would you like to open a company and expand on it? Or would you rather do something else entirely?
- What was your hometown? Do you have any stories you’d like to share about it?
- Tell me about your family? Do you have a lot of members? Who is the oldest?
- Who are your friends? What do they do? Do you get to see them very often?
- Do you miss your home? Or your current place is exactly where you wanted to be?
- Do you have a nickname? What your friends used to call you?
- What kind of movies do you like the most? Is it an action? Drama? Or both?
- Would you rather live in an expensive hotel or opt for camping?
- Do you like dogs or cats? Do you have a pet now? Have you had one before?
- What foreign country did you visit first?
- What kind of skills you have? Are you proud of them?
- Do you play a musical instrument?
- Can you juggle?
- Do you like video games?
- What is the best movie franchise of all time?
Questions to ask a guy to get to know him
After you break the ice, it’s time for some fun. If you want to get to know him deeper you have to ask more specific stuff. It doesn’t mean that you have to ask whether he will marry you but rather questions that are challenging to answer. These are perfect to get to know him better as they force him to solve a puzzle inside his head. If you want to learn more about the man something useful, start with these.
- What would you do for one million dollars? And what you wouldn’t do even for one trillion dollars?
- If the rest of your life you were to live on an island, what kind of entertainment would you bring along?
- What do you think about social media? Are they good or are they bad?
- iPhones or Androids?
- What drives your decision when you pick a smartphone? Is it specs? Looks?
- If you were to encounter something mystical, what things would you do first?
- If you had a chance to meet your favorite actor/musician/writer, what activity would you like to do with them?
- If you were to live for the rest of your life with a pet, would it be a cat or dog?
- Do you think human teleportation is a fantasy or distant future?
- What’s better? Read people’s minds or see through walls?
- PlayStation or Xbox?
- What superhero do you like the most?
- What is your stance on police brutality? Do you think this could be stopped? How?
- What is the most important event of the year?
- Do you like bikes or cars? Why?
Questions to ask a guy you just met
We know that many of you want to learn some good ice-breaking questions and we are more than happy to deliver. After all, it can be hard to pull yourself together with all the stress that comes with meeting new people. We’ve prepared questions to ask a guy you just met online so you don’t have to worry about a thing.
- Do you like this place (website)? What brought you here?
- What makes you smile?
- Do you have a favorite brand? What is it and why?
- What are your talents? Do you plan on expanding on them?
- If you had a million bucks, what would you buy first?
- What sport do you like? Do you have a sports team you root for?
- When you were a kid, what was your favorite cartoon?
- What is the scariest movie you’ve ever experienced? What terrified you the most?
- What crazy thing you did and wish it never happened?
- Do you play a musical instrument?
- If you could teleport in an instant, what place would you visit first?
- What is your favorite meal?
- If you could end one major world problem, what would it be?
- How many times you’ve watched your favorite movie?
- What old thing would you bring back into modern society?
Flirty Questions to ask a guy over text
One of the best ways to learn about a man is to ask stuff through text messages. Why? Cause they will feel less stressed. Whether it’s sex questions or some meaningless discussions, texting is great for such things. We managed to compile some basic Qs to make things less tense. Last but not least, we managed to gather some funny questions you can use to text a guy.
- What is your favorite gif or video that causes you to laugh?
- Send me some music you like to listen to lately?
- Can you describe yourself using stock internet pictures?
- How much time do you spend online?
- What dumb pick-up line you’ve used and it actually worked?
- How many times you’ve watched my profile picture?
- What kind of music do you like the most?
- If you were to dress me up, what costume would it be?
- How would you act if I started kissing you right now?
- Did you try to picture me naked?
- Can you send me some of the best memes you have?
- On a scale of 1 to 10, how do you rate Nicky Minaj Anaconda music video?
- What kind of meme describes your life the best?
- How much is the fish?
- Cinema or Netflix and chill?
Deep questions to ask a guy you like
After you’ve learned so much about the person, it’s time for some deep and somewhat philosophical stuff. Now we know that it can be hard to discuss some worrying things but you absolutely must do so. Serious questions might seem stressful and overly complicated to some people, so it’s best to ask a guy in the question game. That way, he will be less stressed and you’ll be able to learn what you want.
- What do think, can money buy happiness? If yes, how?
- Do you think that drugs are bad or the people that use them?
- What is your stance on global warming? In what way do you think we can solve this issue?
- Is technology more helpful or more damaging?
- In what case the crime is ethical?
- What do you think about the Vietnam war?
- Do you think Marijuana should be legal? Or should we ban it completely?
- Do you think animals should have the same rights as humans?
- How do you cope with stress? What are your methods?
- Is there life after death? Or we just stop our existence?
- Do you think that the modern economy is flawed?
- Is there a fifth government that controls the world?
- Why were the pyramids built? What purpose do they have?
- Is reincarnation possible? What are your thoughts?
- Would you die for your loved one?
Random questions to ask a guy
Phew, now that we’ve covered the deep stuff, it is time for something less intense. Yes, we’d like to ask him some random things. Why? ‘Cause it will ease the overall mood of the conversation and will allow you to get to know them even better. You can use these while talking to a guy you like over text too. So, here’s what you need to learn about a person you like first.
- What would happen if electricity wouldn’t be discovered?
- Can people live without paper? How many products would die out if they could?
- How long can you not breathe underwater?
- Did you know that Pokemon started out as a game and not as kids show?
- If you could live in one climate for the rest of your life, what would it be?
- What was the last meal you’ve eaten? Did you like it?
- Coffee is better with or without milk?
- What was the worst thing you did to yourself?
- Techno or Pop?
- What idiom do you hate and why?
- What song sounds sexy to you but no to everyone else?
- Do you think karma is a real thing?
- Which one is better? Paper books or audiobooks?
- Fish vs Chicken?
- In a hand to hand battle, who would win, Batman or Robin?
Questions to ask a guy you like over text
Now, one of the most common questions we hear is “what questions to ask a guy you like?”. There are many of them but it doesn’t mean that you should ask them all. What you have to do is be specific and pick good questions to hit home. We have such questions on this list and you can use them in texts or in real-life, you decide.
- What are you grateful for the most?
- What was your best childhood memory?
- If you could change one thing about your past, what would it be?
- Can you tell your favorite joke of all time?
- You have three words to describe yourself, what are they?
- When was the last time you felt like crying?
- Do you think love can bloom on the battlefield?
- What are your short-term goals?
- Do you plan on working in a company or do you want to start something yourself?
- What is the scariest thing for you?
- What helps you stay positive?
- Can you name your biggest guilty-pleasure thing?
- What do you seek in a girl?
- What is your passion?
- What makes you feel alive?
Cute questions to ask a guy
If you’re looking for cute questions to ask a guy you like while texting, we got you covered. It can be hard at times to keep such conversations going because very often, men want to look and sound strong. But no worries as we managed to find some very clever ones as they are not cheesy and will help you understand what he prefers in a person.
- Can you describe your ideal date activity?
- Can you name at least one thing you cannot resist?
- What is the most important thing on a date?
- What are your thoughts on the term soul mate? Do you think it is a thing?
- Is there something that will 100% of the time make you smile?
- If you had three wishes fulfilled, what would they be?
- Do you like to cuddle?
- What better way to keep a spark in a relationship?
- Are you soft on the inside?
- What is the longest time you’ve dated someone?
- Are you afraid of spiders?
- What was the first thing you’ve thought about me?
- Can you name your biggest achievement?
- Would you like a fast ride in a car or rather a long walk in a park?
- Whom do you admire?
Funny questions to ask a guy
If there’s one thing a man likes, that’s a good laugh. Hence why we made sure that you know at least a couple of fun flirty questions. We also decided to spice things up and included some fun sex questions to ask a guy you like. Also, a small heads up, some of our fun dating questions are not sure-shots so be very careful with them. Not everyone likes dumb stuff and it all can result in unrepairable damage.
- What was your most embarrassing experience?
- Do you have a celebrity crush that no one knows about?
- Can you name the cutest animal on the planet?
- What would you like me to wear next time (if you plan on seeing the person again)?
- Can you describe your most hilarious moment in life?
- What is your favorite comedy movie and why?
- Which one is more important? Smart or happy?
- Can you recollect what was the funniest thing you did in school?
- Are you the naughty type of guy or a softie?
- What thing you were doing as a kid that today is considered to be silly?
- Can you name a guilty pleasure song that nobody likes but you?
- If you had the ability to pick a superpower, what would it be?
- Is there a game you hate because you always lose?
- What car would you like to give a test drive?
- If I were to come half-naked today, how would you react?
Interesting questions to ask a guy
If you aren’t the type of person to ask funny stuff, we have prepared some intriguing questions to discuss. We made sure most of them are very interesting but do keep in mind that not everyone shares the same enthusiasm as you do. These Qs can be used to ask a guy you like over text and, frankly, that’s where we tested them first. So, here are some interesting ideas.
- What are your thoughts on WWII? Do you think there will be a WWIII?
- What do you like to do in your free time?
- Do you have a pet? What is it? What’s its name?
- You are tasked to provide a TED talk tomorrow, what is your subject?
- Is there are a fictional character you relate to the most?
- Name your favorite 90s movie?
- What do you idolize and why?
- Was there something in your life that made you rethink your entire lifestyle?
- Can you name three songs you can listen to eternity?
- Can you teach me something in the next five minutes?
- What are your thoughts on circus animals? Should they be there or not?
- When did you realize that you are no longer a child?
- Name three things that can inspire you?
- What is your lamest skill and why do you think it’s lame in the first place?
- What is your biggest turnoff?
Personal questions to ask a guy
Very personal, or more appropriately super-personal stuff to ask a guy you like over text can lead to all sorts of outcomes. Some things are best said face-to-face rather than text. You must be 100% sure that both of you are ready for such talks. As for the questions themselves, they range from really personal sexual issues to things that make each of you happy. You get the idea.
- Are you a religious type of guy?
- What are your thoughts on a higher power?
- Long term commitments or short flings?
- How many kids would you like to have?
- Do you think taxation is theft?
- Did you have moments in your life when you thought you were gay?
- Should all couples marry or is it just formalities?
- What is equality in a relationship?
- Can you adopt a child?
- Do you want a girl or a boy?
- Once there is a baby, who would have to leave their job? Why?
- In bed, do you like being on top or at the bottom?
- What kind of sex pose do you like most and why?
- What is the most devastating thing a parent can do?
- Who should do the housework?
Relationship questions to ask a guy
If you think you are ready to explore the other side of your potential partner, these good relationship questions will surely come in handy. As usual, we’ve mixed some serious relationship questions and some funny ones. Regardless of which one you use, through them, you must learn how he feels and what are his thoughts on the whole situation. You’ll definitely learn something new and it will make him feel valued at the same time.
- How many girls did you have before me?
- On a scale of 1 to 10, how much do you like me?
- What is the best thing about me?
- Have you ever been in love?
- What are some things you’d rather not tell to me?
- What is love to you? Do you think it’s chemistry or is it a soul thing?
- How long do you think we will date?
- Do you feel tense or comfortable around me?
- What are your thoughts on pornography?
- What do you think can damage our relationship?
- What do your friends think about me? Do they like me?
- Would you love me if I lost physical appearance?
- When was the first time you’ve kissed a woman?
- On a weekly scale, how much should a couple have sex?
- What are your fantasies?
Awkward questions to ask a guy
Do you know what can brighten-up your day? That’s right, some really awkward questions. If you run out of ideas, awkward Qs is the way to go. These will surely sparkle the mood, especially when you land on those most awkward sex questions. Now, before you try to ask those Qs, make sure you’re on the same page. Otherwise, it will make him think the stuff he shouldn’t and nobody wants that.
- Was there an adult time when you peed your pants?
- What was the most awkward thing you’ve said during sex?
- Did you ever fall asleep during sex?
- How long can you last not peeing?
- Do you have an embarrassing fantasy? What is it?
- What was the stupidest thing you did during sex?
- If you could, would you give birth to a child?
- What fears you have others don’t?
- On a scale of 1 to 10, how much do you want to bang me?
- What is the best pun you know?
- What would you choose, play video games to earn money or have sex for free?
- Are you afraid that someone sees you naked?
- Do you have naked pictures of yourself?
- Did you think that alcohol makes some women prettier?
- Can you tell your absolute worst joke?
Weird questions to ask a guy
When someone is looking for it, this can only mean two things. Both of you like funny weird questions or you are so deep into a relationship that really weird questions are the only ones that are left to explore. In any case, we’ve prepared some weird sexual questions to ask a guy you like, as well as some less sexy for good measure. Let’s take a look at all of them.
- What song would you like to be played at your funeral?
- When was the time when the phrase “looks can be deceiving” was actually correct?
- Would you go on a date with me if I said I like to eat cats?
- Do you keep porn on your PC?
- What kind of spying technology would you like to have?
- Do you think that someday humanity will live like Adam and Eve?
- Do you like to play games where you have to take your clothes off?
- Did you ever have sex in an upside-down position?
- Is there a celebrity you wouldn’t mind doing?
- How often do you operate on autopilot?
- How long can you not sleep and still be somewhat productive?
- Have you ever been to a woman’s bathroom?
- What would you like to do on top of the Giza pyramid?
- If you were to teleport to a fantasy world, what would it be?
- What kind of melody describes you best?
Flirty questions to ask a guy you like
We think good flirty questions help couples drive their decisions. And this is precisely what we prepared. We made sure that some of the below listed Qs can provoke actions in case you want to tell him that you are ready for something bigger. We like to call them fun flirty questions for developing your sexual relationships. By the way, you can use them to ask a guy while texting but again, we’d talk in person as it is the reaction that you must follow next. Yet, if you still want to do it over text, you can but you’ll need your intuition to figure out the response.
- What part of my body do you like the most?
- Can you keep a secret? I have something spicy to tell. (presumably, you really have)
- Don’t you think it is a little bit too bright in here? Can we turn off some lights?
- How much do you need to feel tipsy?
- Do you agree that this place is a little bit crowded?
- You have a personal tailor or does that shirt look perfect on you?
- Isn’t it a bit too hot in here?
- Think you can beat me in an eye contact contest?
- When it comes to a woman’s body, what part do you find the sexiest?
- What was that French thing called?
- Shall thee be tempted to lay your teeth into my… dessert?
- Can you show me what a perfect kiss looks like?
- Are you afraid when girls do the first step?
- What do you wear when you go to bed?
- Would you like to count my tattoos/birthmarks?
Sexual questions to ask a guy
Before cover this part, it is important to understand that these are only used when you already had sex or are super close. After all, personal sexual questions aren’t meant for people who didn’t hit home yet as they can do a lot of damage. Now that it’s out of the way, let’s take a look at some both weird and funny sexual questions. Oh, and by the way, men love some sexual truth or dare questions so make sure you use them effectively.
- So I have this cool movie on the DVD but it’s all lonely here, would you join me?
- Is it me or is it cold, can you bring a blanket for us?
- What do you think about costumes and role-play.. in bed?
- Oh wow, is it me or did someone turned the AC up? It’s hot in here!
- Gentle or Rough? Which one do you like best?
- Do you think we can fix a few things since the last time?
- Where would you like to have sex? In the bed or on the table?
- Would you like a massage?
- Can you share your sex fantasies with me?
- Have you ever laughed during sex?
- Care to watch some porn with me?
- What are your thoughts on the basic instinct movie? Do you think I could be sexier?
- Can you tell me what would you do with me in bed?
- What turns you on?
- What was the most embarrassing thing you’ve done during sex?
Dirty questions to ask a guy
And the last ones are dirty truth questions to ask a guy over text. These are not for everyone and you really have to know when to ask them. But even so, we made sure that if you opt to use our funny dirty questions you have some room for flexibility. And by flexibility, we mean that they aren’t just funny dirty, rather dirty sex questions too.
- Want to learn what my lips taste like?
- What do you say we see who has a bigger bed of the two of us?
- I have a spell that will make you lose all your clothes, want to find out if it works?
- Can you tell me what is your most sensitive body part?
- I think it’s time I share a little secret with you.. don’t you agree?
- I think I need a hug, in bed, naked… Don’t you?
- Would you share your bed with me?
- I’m sorry, but why do I always forget about everything when I see you?
- What do you say we leave this dinner table for something more comfortable?
- Can you show me a naked picture of you?
- Do you think you have enough space on your bed?
- What if I tell you that I like to play dirty games?
- What is the color of my underwear?
- Can you guess what is on my mind right now?
- What do you say you stay for the night?
So there you have it, our ultimate 265 questions-long guides to an interesting relationship start. We hope these questions will spice things up for you and help you evolve your relationship to something bigger. Some of them are perfect for text and others are best said in person. But remember one thing, don’t be afraid to ask stuff. The more you ask, the further you go. After all, he is just as nervous and stressed as you are. Your main priority is to form an environment where both of you will feel comfortable. If you are still on the fence, we suggest that you mix and match and see what works in your scenario and let us know the results. And that’s about wraps for today. Be sure to come back as we post content like this all the time.