Questions to Ask a Guy

True story: a friend of mine met a guy who asked for her phone number and Snapchat username so he could text her. For over a week, their conversations went something like this:

Him: Wyd?

Her: Not much. Wyd?

Him: Talking to the most beautiful girl in the world.

Her, gagging, but still trying to keep the conversation going: What did you do today? Anything fun?

Him: It was all pretty boring…until I go to talk to you.

Her: *gags* *rolls eyes* *puts phone down and gets back to real life*

Day after day, that was the extent of the conversation. Eventually, when it became apparent that this guy’s soul was about as deep as a puddle, my friend cut him off. But it got me thinking, what are some interesting questions to ask a guy to really get to know him? What questions can you ask to engage a guy’s attention, get a conversation going, and move the conversation to the next level?

In a world where most people get to know each other via text and social media, it can be hard to know how to what to ask to get a good conversation going. Asking the right questions is a vital part of that process.

So this post comes to you in several parts. Some of these are great questions to ask a guy you like, or a guy you want to get to know. They’re good for one-on-one conversation, and some are good questions to ask guys over text. Some of them would be great to ask a guy friend…or perhaps someone you’d like to be more than a friend.

Good Questions to Get to Know a Guy You Just Met

There are lots of posts out there with suggested questions to ask a guy, questions like, “If you could be any fictional character, who would it be?” or, “If you could live on a fictional planet, what color would the grass be?” All in all, they’re not bad questions, but they don’t take into account one very important factor: YOU JUST MET THIS GUY. Save the questions that will require some deeper thought (not to mention creativity) for a little later, and don’t be afraid to start with the basics.

What do you like to do on the weekends?

What do you do to chill after a long day?

Which do you prefer: books, movies, or television?

The answer to #3 will determine some follow up questions, like:

• Who is your favorite author?
• What kind of movies do you like?
• What is the last show you binge watched?

Do you prefer sports or video games?

Do you prefer cats or dogs?

What do you do for a living?

What is your dream job?

If you could remove one color from the world, what would it be?

If you could remove one person from your life, who would it be?

What was your favorite movie as a child?

Here are some more interesting things to ask a guy by text:

What would you do if you could be invisible for a day?

If you could change anything about yourself, what would it be?

Do you like your name? What would you change it to?

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

What is your most sentimental possession?

These are all good things to ask to get to know a guy you just met. They’re light, easy, and don’t require much thought. But let’s say you’re ready to take the conversation to the next level…

Good Questions to Ask to Get to Know a Guy Better

These questions are great when you’re past the “just met” phase, but still have a long way to go to the “soul mate” stage. Here are some more great questions to get to know him. Pay close attention to his answers to these questions, and remember to follow up. These are just conversation STARTERS. It’ll be up to you to keep the conversation going! Some of these questions are simple suggestions to get you thinking. Use your imagination and your personality to make them awesome!

If you could be famous for something, what would it be?

If you could live anywhere in the world, where would you choose?

Which are you most afraid of: spiders or snakes? Heights or failure? Clowns or never seeing     the Super Bowl in person?

As a child, which rule did you enjoy breaking the most?

Who is your best friend?

Seems pretty basic, right? But this is ALWAYS a good question to ask a guy you like because it proves that you’re really interested in getting to know him.

Follow up questions:

• How long have you known him/her?
• How did you meet?
• What is the craziest thing you’ve done together?

The next few sections are themed questions. These are interesting questions to ask a guy at any stage in the relationship, but they can be especially fun while you’re still in the “getting to know each other” stage.

Questions about “firsts”

Who was your first love?

What was the first movie that made you cry?

How old were you the first time you kissed someone?

What was your first broken bone?

What was your first concert?

Questions about “lasts”

What was the last movie you watched/book you read?

Who was the last person to break your heart?

What was the last thing you did that you instantly regretted?

What would you like your last words to be?

Who is the last person you kissed?

Questions about family

Depending on how long you’ve known the guy you’re trying to get to know better, these can be tricky questions. You never know what kind of family questions will trigger emotion, so proceed with caution!

How many siblings do you have?

Are your parents still together?

Who is your favorite cousin/sibling/aunt/uncle/pet?

What are your family reunions like?

Did your parents (or guardians, grandparents, etc.) ever have a specific dream for your life?

“Have you ever” questions

My suggestions here are pretty tame, but feel free to use your imagination 😉

Have you ever stolen something from a store?

Have you ever felt “love at first sight”?

Have you ever gone skinny dipping?

Have you ever dined and dashed?

Have you ever gotten lost and turned it into an adventure?

“What’s the Weirdest” questions

What’s the weirdest song on your playlist?

What is the weirdest food you’ve ever eaten?

What is your weirdest superstition?

What is your weirdest dream job?

What do you consider to be the weirdest thing about yourself?

“Would you rather” questions

Would you rather go on a blind date or hang out with your grandma?

Would you rather live in a world without coffee or French fries?

If you had to choose, would you rather be blind or deaf?

Would you rather live in a world without books or without social media?

Would you rather lose all your hair or have to spend a month dressed as the opposite gender?

Questions to Ask a Guy on a Date

Okay, so you’ve been texting for a while, and it’s time to take the next step: an actual date. These questions will help you keep the conversation going if you find yourselves falling into an awkward silence. For more questions and great advice on navigating that first date, click here.

What kind of things really make you laugh?

What is your favorite place in the entire world?

What is your biggest goal in life right now?

Follow up questions to this one might be:

• What is the next step you need to take to reach that goal?
• What, if anything, is standing in your way?

What were you like as a kid? or a teenager?

What is your biggest pet peeve?

What terrible movie do you love?

Do you quote TV or movies in normal conversation? What’s your most used catch phrase?

What song do you know every single word to?

What character on TV do you find most annoying?

What do you think is the most annoying song on the radio right now?

What is the craziest thing you’ve ever done?

Truth Questions to Ask a Guy

Truth questions for guys can be tricky, so you might save these to use as questions to ask the guy you’re dating. Remember, be prepared to answer these yourself! Never ask a guy you like questions that you aren’t willing to answer. In fact, in order to break the ice, it might be better to tell him your answer while he’s thinking of his own.

What are you most self-conscious about?

What do most of your friends believe about you that is totally untrue?

What is the biggest lie you ever told just to impress a girl?

What is the silliest thing you have an emotional attachment to?

What is the most embarrassing thing you’ve ever been caught doing?

What is the most embarrassing thing you’ve ever caught someone else doing?

Have you ever loved someone who didn’t love you back?

What do you really hope your parents never find out about?

Are you a natural risk taker?

What is the riskiest thing you’ve ever done?

What is your go-to guilty pleasure movie, TV show, or food?

What is the most embarrassing picture on your phone?

How often do you take a selfie?

Have ever sent a dirty picture of yourself?

Have you ever asked someone to send you a dirty picture?

Serious Relationship Questions to Ask a Guy

Okay, you’ve made it past the dating stage and you’re developing a serious relationship. What are some good relationship questions to ask a guy, things you’d really like to know? What are some important questions to ask?

CAUTION: Sometimes a girl’s idea of what a “serious relationship” is  doesn’t match the guy’s idea. Only ask the following questions if you’re sure you’re on the same page, AKA, you know these questions won’t run him off.

CAUTION AGAIN: Some of these questions might be deal breakers for you in your relationship. Only ask them if you really want to know the answers.

Do you have any close female relationships other than me?

Do you have feelings for any of your exes?

How do you respond when something makes you angry?

What experience has most shaped who you are today?

What first attracted you to me?

Who, if anyone, are you holding a grudge against right now?

Where do you see yourself in five years?

If you were offered a dream job in another location, would you ask me to move with you?

Do you have financial goals, like savings or retirement, and how much of a priority are they?

If I asked one of your exes how you treated them, what would they say?

What’s more important to you: working toward a goal or living in the moment?

Do you want to have children someday?

What type of affection is most annoying to you?

How do you prefer to show affection?

If I had a middle of the night emergency, would you want me to call you?

Love Questions to Ask a Guy

Now that you’re in a serious relationship, there might still be some questions that you haven’t asked and he hasn’t answered on his own. If you’re looking to build intimacy, there are certain love questions to ask him to help get the ball rolling. Or maybe there are just some things you want to know! Read on for suggestions to ask the guy you think you might be in love with, or who you think might be in love with you.

REMEMBER TO RECIPROCATE! Be sure to answer every one of these questions (except for maybe the last one), even if he doesn’t ask them directly.

What was the first thing you noticed about me?

What was your first impression of me?

Did your first impression change after our first date?

Is there anything you’ve ever wanted to ask me, but haven’t had the courage?

What does being in love feel like for you?

Have I ever done or said something that hurt you unintentionally?

This might be the best question to ask a guy you want to have a long-term relationship with. If he answers honestly it will give you a lot of insight into his emotional needs and can help you figure out your role in meeting those needs.

Questions to Ask a Guy Friend

Whew! That’s a lot of questions! But you’ll notice the progression of this post doesn’t account for every scenario. What if you meet a guy, begin texting, maybe even go on a date, but then realize you make better friends than lovers? What are some good questions to ask a guy FRIEND?

Truthfully, you could just read back through this list and find some great questions to help you get to know a guy friend. Some of them might be even funnier and less awkward when you’re asking them without the pressure of a romantic relationship gripping the two of you like a vice.

Questions like “Who is your best friend?” are still important – perhaps even more so, now that you’ve drawn the “just friends” boundary line. And questions about his family might seem more like a friendly “get to know you” discussion and less like an interrogation ala [insert any TV crime drama here] if he doesn’t think you’re grilling him for information about his history and background to search out commitment issues.

Still, if you’re looking for more suggestions about what questions to ask a guy keep the conversation going, here are a few that are great questions to ask guy friends, whether you’re looking to take your friendship to the next level or not.

If you could travel anywhere in the world, where would it be? How long would you stay? Can I go in your suitcase?

What song always puts you in a good mood when you hear it?

What song makes you think of something sad every time?

What was your favorite TV show to watch with your family?

What food always puts you in a good mood?

Who is the funniest/meanest/smartest person you know?

What was the best vacation you’ve ever had?

What one word would you use to describe yourself?

What one word would you use to describe me?

What is the one thing that you wished everyone (or someone in particular) would notice about you?

What do you think people notice first about you?

Have you ever met a famous person?

What famous person would you love to meet?

What is your greatest, silliest skill?

What is the skill you’ve given up trying to learn?

Do you play (or wish you could play) any musical instruments?

Who has had the most positive influence on your life?

Would you consider yourself a role model?

If you knew you could try one thing without failing, what would it be?

Questions to ask a guy NOTES