20 Fun Questions to Get to Know Someone – The Only List You Need

Moving past the acquaintance stage to knowing someone on a deeper level requires digging a bit deeper into their lives using questions.

But not just any type of question.

Questions that require a simple “yes” or “no” will not cut the deal. You need to ask open-ended questions that let the other person open up and elaborate.

Keep in mind that you don’t want the other person to feel they are under some kind of inquisition. Although you want to ask questions about topics that reveal the other person’s dreams, goals, and general thoughts, your questions shouldn’t be like formal interviews.

Fun should be your watchword.

Here are 20 fun questions to get to know someone.

Questions About Likes

A good place to start is to find out about the other person’s preferences. It is usually better if you ask follow-up questions that will make your conversations flow naturally. For example, if you discover that they like birds, you should go one step further to ask what species of birds they like the most or what specifically about birds hold their interest the most.

With a little patience (because you don’t want to come across as pushy), you will increasingly become better acquainted with the other person and even grow closer to them in a short time. The key is to keep things light-hearted and exciting so that the conversations are not forced. You want to flow naturally into sharing personal stories with each other.

Some fun questions about likes or preferences that you could ask to know someone better include:

1. How did you get into your hobbies?

Hobbies are generally things that people enjoy doing, which makes it an easy topic for them to talk about.

When you ask this question, you are effectively doing two things:

• You set the tone for a pleasant conversation
• You let the person share their story instead of just what their hobbies are

Asking “what’s your favorite hobby” is good, too, but may need several follow-up questions to get the other person to reveal things about themselves to you.

But when you ask how they got into what they enjoy doing, you open the floodgates of something they are passionate about, which can make them go on and on about different aspects of their lives that you didn’t directly ask about.

2. What is that one book you won’t get tired of reading?

The books we read can significantly influence our views, ideals, and values. If you know what someone enjoys reading, you will be able to make sense of their value system.

A good follow-up question to this one would be something in the lines of, “So, is there any particular reason you prefer X type of books to Y?”

If you only stop at asking about their favorite book, that answer alone may not give you a clear idea of the genre of books they enjoy reading. To get to know someone better, you will need to probe a bit further to know what collection of books shapes their general perceptions.

If you handle this well, you will not only enjoy a rich conversation about favorite books, but about authors, ideologies, and most of all, you would have known them a little more than before.

3. If you were to binge-watch a TV show, what would it be?

This question will also help you to know someone a bit better in much the same way their favorite books would, especially if you dig a bit deeper to know what characters in the TV show intrigue them the most.

Most people like fictional characters that reflect a trait they cherish and hate or dislike fictional characters that exemplify a trait they don’t like.

Do you now see how digging in a bit deeper could reveal what the other person likes and dislikes? If you only asked a question without seizing an opening that presents itself in their answers to make further inquiries, you may not get a clear picture of what they prefer.

4. What holidays do you look forward to, and why?

This is a good way to know someone on a personal level as the question allows them to disclose to you their idea of fun.

Whether it is New Year’s Day, Christmas, Thanksgiving, Independence Day, or any other holiday, the level of excitement that goes into preparing for it can tell you a lot about a person’s value system.

Don’t forget to add the “why” part of the question, as that is the secret ingredient that will make the other person share a little more of their personal life with you.

If you ask, “What’s your favorite holiday?” it is more like a close-ended question. The response is usually straightforward and ends a conversation before it even gets started. But framing it as stated above makes it an open-ended question that allows the person to go into lots of details.

Pro tip: It is best to discontinue (at least for the meantime) once you notice the other person losing interest in answering your questions, or continuing the conversation. Pressuring them into answering questions can make them hide things from you and may even lead to resenting you.

Fun Questions to Get to Know a Girl

Pay attention here, guys!

There are lots of questions to ask a girl ranging from flirty to interesting and even deep questions. But if you simply want to get to know a girl with no strings attached (at first), it is best to ask her fun and casual questions.

But make no mistakes; her answers can provide deep insights into who she is, what she likes, and what she expects in a partner. So pay close attention to her responses.

However, keep things light. You don’t want her to think she’s under scrutiny. There are many things a girl can find attractive in a man; interviewing her is definitely not one of them (unless, of course, she’s looking for a job).

Remember that these are supposed to be fun questions to get to know someone, so ask them in the most amusing way as possible.

Here are some fun questions that most girls won’t hesitate to answer, which can help you know them better.

5. What do you still enjoy doing even though you’ve outgrown it?

Expect cute and funny answers here.

But the goal is not just to make her laugh. Instead, it is to get her to talk about nostalgic activities that she enjoys, even if she is too old to do them.

If you are struggling with conversation starters or finding the right questions to ask a girl, perhaps this one might just be what you need.

6. What spontaneous thing have you done recently?

This is a good question that lets you take a quick peek into a girl’s lifestyle?

Is she adventurous or prefers everything planned out with little room for surprises? Is she someone who can easily go with the flow of the moment, or someone that thinks ten steps ahead?

While it may be difficult to accurately form an opinion of her from just one response, you can ask follow-up questions depending on her answer and even take things further into a deeper conversation.

7. If you had the power to choose a decade to be born in, what decade would that be and why?

The answer to this will likely tell you a lot about her fashion sense, type of music, and her general ideology about glitz and glamour.

That “why” part of the question serves as a great way to start a conversation because it will allow her to say more than just a time in history she prefers but the reasons she prefers it.

And her reasons will tell you what type of person she is trend-wise.

8. If you have to marry one fictional male character, who would it be?

She may chuckle at first.

And then probably tilt her head to think for a while before she responds.

Whatever her response, you will be able to discover what she looks for in a partner. A lot of girls fantasize about their ideal man being like a fictional male character they have come to adore.

In many cases, it may be difficult to pin her choice to just one fictional male character. That’s probably because she admires several other traits in different characters and hopes her dream man will combine most, if not all, of them.

Well, if you are hoping to build a relationship with her, at least her response will give you a clue to what she expects from you, and you’ve gone a step further in getting to know her better.

Here’s a disclaimer, though. This is not an exact science. Nevertheless, that’s a chance that her response will give you a glimpse into what she hopes (on some level) to find her type of man.

Bonus Fun Questions to Get to Know Someone – A Girl to be Precise.

• Suppose your house was on fire, what would you grab?
• If you’re feeling down, what’s one thing that can make you feel better in an instant?
• What is your number one guilty pleasure?

Pro tip: Avoid questions that can make the other person feel as if you’re violating their privacy, especially early on in the relationship (whether they are your colleague, friend, or potential intimate partner).

Fun Questions to Get to Know a Guy

Getting a guy to answer your questions is relatively easy because a lot of guys find it enjoyable to talk about themselves. Ironically, men are generally not as talkative as women.

There’s actually a study that shows that women have more of Foxp2, the language protein, which makes them more talkative right from an early age. It is claimed that women can speak up to 13,000 words more than men every single day!

That’s just by the way, though. Let’s get back to fun questions you can ask a guy if you really want him to open up to you.

As long as you don’t ask close-ended questions, you are likely to get to know a guy pretty quickly.

Another thing to keep in mind is that men generally are good at compartmentalizing their lives. Meaning, they tend to focus on one thing at a time.

Why is this important to know? If a guy is focused on one thing, you’ll hardly get him to talk about something else. So, make sure your fun questions are aligned with what he is doing at the moment.

This also explains why men are less talkative – one topic doesn’t automatically sprawl in every possible tangent, as it is common with most women. Guys are likely to answer a question directly without going into other areas.

Check out these fun questions to ask any guy you will like to know better.

9. What secret skills do you have?

One of the fastest ways to get a guy to freely share personal information with you is to stroke his ego! And I mean that in a good way.

People usually have a few things they can do but which many people know nothing about. This is why most guys will be very pleased with this question (some will actually be excited) because it gives them the chance to impress you with their secret skills.

This question gives you an insight into what this person can do exceptionally well, even though he is not letting many people in his life to know about it. Perhaps others don’t appreciate him for his skills or some other reasons.

Asking him what his secret skills are, allows him to open up on a whole new level that many people don’t know.

10. What’s your most hilarious kitchen fail?

Okay, now this is something that almost always gets a guy to tell you a lot about his flaws without feeling awkward. Instead, he is most likely to laugh his heart out while sharing his seemingly embarrassing kitchen moment with you.

Regardless of how good a cook he is, most men have experienced times when they failed miserably trying to cook a dish or two. So, go ahead and ask even if he’s a chef!

You can use this question to ask other follow-up questions such as:

• What is the best dish you’ve ever made?
• Have you ever considered being a chef or opening your own restaurant? (If he doesn’t have one yet)
• If you could only eat one food for the rest of your life, what would that be? (Lot more fun than asking “what’s your favorite food?”)

Just remember not to shoot all of these questions at the same time. Let them flow naturally during the course of your conversation, and make sure to ask them in a laidback manner.

11. What are the three things you can never spend money on?

This is a good way to find out what a guy values and what he considers as a total waste. Of course, you don’t know someone well enough until you know their values.

12. What is one thing most people don’t believe about you?

An honest answer to this question will definitely dig up something you never knew about the person.

You can vary it by asking, “Is there something about you that I wouldn’t believe if I didn’t hear it directly from you?”

The goal is to get the other person to dig deep and reveal one or more things about them that are less known.

Pro tip: It is best to steer clear of potentially controversial topics, such as political views and faith-based questions, especially when you are just getting to know a guy. Wait until you know someone very well before you ask, “Are you a Republican or Democrat?” “Are you religious or spiritual?” or “What spiritual beliefs do you subscribe to?” A lot of men can be very passionate about their political views. If you say something against their affiliations at the start of a friendship, you might jeopardize your chances of getting along with them.

Random Fun Questions to Get to Know Someone

Random questions are a great way to get to know someone better, whether they are colleagues at work or someone in school you want to know better.

These questions are usually out of the blue, so it gets the other person to pause and think before responding. It’s a good way to get past the “yes” or “no” boring answers.

What’s the perfect time to use random questions? Use them when you notice a lull in your conversation.

For example, if you are with new a girl that you’ll like to know better, and there’s an uncomfortably long silence threatening to kill your conversation, ask something out of the blues – completely unrelated to something you’ve been talking about or remotely related to the situation at hand.

Doing this will make your random questions to have more impact on her as she’ll likely be taken aback and wonder what’s going on in your mind. As she thinks of an answer to your question, she’ll also be intrigued by your personality and want to know you even better!

Here are some random fun questions to get to know someone better. They will help when you are looking for a good conversation starter.

13. What do most people get wrong about you?

This random question digs into the common misconceptions about the person you’re asking. Most people never get the chance to explain themselves, which is why they’re most likely to use the answer to this question to clear the air. This random question can get you to discover some really deep things about the other person.

14. What are some of the cheesiest pick-up lines you’ve ever heard or used?

If you’re talking to a guy, ask them the lines they’ve used. If you’re getting to know a girl, ask them one they’ve heard and couldn’t help but think, “lame!”

This random question will likely bring up some very entertaining responses that will get you both laughing hard!

Here’s the thing, when someone gets comfortable enough to laugh their hearts out when they spend time with you, they’ll want to experience that pleasurable feeling again and again. This is a surefire way to get them to build a stronger bond with you and share other things about tier lives with you.

Besides offering amusing answers, this is a great way to know what turns a girl off, and some insight into a guy’s dating habits.

15. What is the funniest joke you’ve ever heard?

As random as this may seem, it is a great and light-hearted way to start a conversation.

A joke, especially one that the other person really enjoys and even tells it by themselves, is a good way to take off the pressure and awkwardness that usually accompanies serious conversations.

16. What skill would you like to master even if it takes forever?

Pose this question when you want to know about someone’s interests, especially if you think they are stuck doing something they don’t really enjoy.

You may not be able to give them what they truly want to do, but letting them talk about it is an excellent way to allow them to dive deep into their true passion and interests.

But since you want this to be a random question, it is best not to bring it up when they are feeling incompetent or less effective in their current endeavor as that will likely make them feel unfulfilled.

When is the best time to ask this question? Just about any time during a casual conversation is good. But for a dramatic effect, consider bringing it up when the other person is ready to talk about what he or she is good at.

This is a great question that can turn small talks into real talks.

Bonus Random Fun Questions to Get to Know Someone

• When was the last time you cried? (Don’t ask a man this, unless you are a woman!)
• If you had a million dollars right this minute, how would you spend it?
• What one question would you ask someone you like if you are sure you’ll get an honest answer?

Pro tip: Getting to know someone is a two-way street. You need to be warm and inviting if you want the other person to feel comfortable enough to share their personal information with you.

“Would You Rather” Questions

What’s makes a question fun if you have to think too deeply to answer it?

Here’s the thing, a question can be fun with a quick and snappy answer, yet it will tell you a great deal about the other person.

That’s where the “would you rather” questions can come in handy.

What’s the best time to use this type of fun questions to get to know someone?

Because this set of questions takes more of a quiz format, they are great when the atmosphere is playful. For example, you can use them when you want to play a little question and answer game or something similar.

Here are 4 “would you rather” fun questions to get to know someone better.

17. Would you rather make less money doing a job you love or more doing one you hate?

Want to know a person’s ideology about money? Ask this fun question.

It is more fun and polite than directly asking if the person likes money more than their passion (which can be disrespectful and insulting).

The answer to this question will tell you if they will follow their passion or simply opt to make ends meet as long as the pay is right.

Keep in mind that you’re not trying to judge them. Instead, you are trying to know them better.

18. Would you rather order in or cook?

This question does not necessarily seek to know whether a person has culinary skills or not (although, it is a good way to find out whether someone enjoys cooking, too).

Instead, you can use this question to know:

• If they have a busy schedule that leaves little to no time for preparing their own meals
• If they have all the time in the world to cook their food
• The person’s favorite restaurant (if they prefer to order food)
• Their favorite dish (if they prefer to cook)
• Their eating habits (whether they eat junk or healthily)

Of course, you need to ask follow-up questions to discover these details.

19. Would you rather lose your sight or your ability to love?

 

Okay, I know I mentioned earlier that these questions are usually quick to answer, but this particular one can make the other person pause and think for a while before answering.

The answer to this question will make you know if the person is more practically inclined or tends to lean more on their emotions.

But like every other question on this list, there’s no way to reach a concrete conclusion about a person’s personality trait just by asking one question. Again, this is not an exact science, but it can offer you helpful insights.

20. Would you rather be left alone when you are upset, or you like someone to comfort you?

This question will usually meet a ready answer, making it come across like a close-ended question. For this reason, it is best to have some follow-up questions handy.

Guess what the easiest follow-up question is?

“Why?”

That’s it. A simple “why” can keep the conversation going.

Kids use this question a lot.

Whatever answers someone you want to know gives, following up with a simple “why” can make them dig deeper and reveal more of themselves to you.

So, if they said they prefer to be left alone, ask why. And if they say they like someone to comfort them, again, ask why. But don’t use it the way kids do. They can get on adults’ nerves just by asking “why” unendingly!

Pro tip: In most cases, answering a question yourself can encourage the other person to provide the answer you are looking for. For example, you could say, “I love going to the nearby water park on my free days. Playing in the water makes me feel alive and puts me in touch with my inner child! What about you, what’s your favorite way to spend your day off?”

Tips to Choose the Most Appropriate Fun Question

Don’t worry if you find it a bit confusing or overwhelming to pick an appropriate question for your situation. Here are some tips to help you choose the right fun questions to get to know someone in any situation.

Who Are You Trying to Know More About?

This is the first and most important consideration when thinking of fun questions to get to know someone.

Who exactly do you really want to know? Are you trying to know more about a girl you like and hope to date, or one you think will be a great friend with no strings attached?

Your questions will depend on who the person is and the direction you hope to steer the relationship toward – good friends, dependable colleague, bestie, or lover.

What’s the Situation?

If you are with other friends in a casual setting (like a party, for example), it is best to choose a question that is relaxed and will not likely embarrass the other person even if a third party gets to hear their answer.

For example, you could ask them any “would you rather” questions.

But you definitely shouldn’t be asking a girl what her guilty pleasure is when there are other people around. That’s not how to treat a woman in public.

It is best to reserve such questions and other deep personal questions for when you are alone with the other person.

Talk About Things You Like

Choose a topic that you really enjoy talking about, and ask questions around that. Thing is, the other person will probably ask you the same question or something similar, too. You’ll be quick to give an answer if it’s something you like to talk about because you are interested in the topic.

Besides, you’ll be more comfortable asking follow-up questions if you talk about things that you like.

Remember that getting to know someone goes both ways. You can’t be asking to know someone when you are secretive or not showing interest in answering their questions.

So, if there’s someone you’ll like to know better, choose a few from this list and ask them during one of your casual conversations.